Chemistry: Paper 4

Candidate
Centre Number Number
Candidate Name
CAMBRIDGE INTERNATIONAL EXAMINATIONS

General Certificate of Education Advanced Level
CHEMISTRY 9701/4
PAPER 4
MAY/JUNE SESSION 2002
1 hour
Candidates answer on the question paper.

Additional materials:
Data Booklet
TIME 1 hour
INSTRUCTIONS TO CANDIDATES
Write your name, Centre number and candidate number in the spaces at the top of this page.
Answer all questions.
Write your answers in the spaces provided on the question paper.
INFORMATION FOR CANDIDATES

The number of marks is given in brackets [ ] at the end of each question or part question.
You may lose marks if you do not show your working or if you do not use appropriate units.
FOR EXAMINER’S USE
TOTAL
This question paper consists of 11 printed pages and 1 blank page.

MML 1439 4/01 S16048/2
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© CIE 2002 UNIVERSITY of CAMBRIDGE [Turn over
Local Examinations Syndicate
2 For
Examiner's
Use
Answer all the questions in the spaces provided
1 (a) Write an expression for Kw.
.................................................................................................................................... [1]
(b) Use your expression to help you calculate the pH of 0.200 mol dm–3 NaOH(aq).
..........................................................................................................................................
.................................................................................................................................... [2]
(c) The pH of 0.200 mol dm–3 NH3(aq) is 11.3. Explain why this answer differs from your
answer in (b).
..........................................................................................................................................
.................................................................................................................................... [1]
(d) A 20.0 cm3 sample of 0.200 mol dm–3 NH3(aq) was titrated with 0.100 mol dm–3 HCl.
On the following axes, sketch how the pH changes during this titration. Mark clearly
where the end point occurs.
14
pH 7
0
0 10 20 30 40 50 60
volume of added acid / cm3
[3]
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(e) From the following list of indicators, put a tick in the box by the side of the indicator you
consider most suitable for this titration.
pH at which colour place one tick only

indicator
changes in this column
methyl violet 0.0 - 1.6
methyl orange 3.1 - 4.4
bromothymol blue 6.0 - 7.6
phenolphthalein 8.3 - 10.0

[1]
(f) A solution containing NH3(aq) and NH4Cl(aq) acts as a buffer solution, resisting
changes in pH when acids or alkalis are added.
Explain with the help of equations how this mixture acts as a buffer.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
[Total: 10]
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4 For
Examiner's
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2 The ester 4-nitrophenyl ethanoate hydrolyses in alkaline solution according to the following
equation.
O O
CH3–C–O– –NO2 + 20H – CH3 –C–O – + – O– NO2 + H2O
colourless yellow
(a) Suggest, and briefly describe, a suitable experimental technique for studying the rate
of this reaction.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [4]
(b) The reaction rate was studied using two solutions of different hydroxide ion
concentrations.
run A: [OH–] = 0.20 mol dm–3
run B: [OH–] = 0.40 mol dm–3
The following graphs show how the concentration of the ester, 4-nitrophenyl ethanoate,
varied over time in the two runs.
0.001
0.0009
0.0008
0.0007
[ester] / mol dm–3
0.0006
0.0005
0.0004
run A
0.0003
0.0002
run B
0.0001
0
0 10 20 30 40 50 60
time / min
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(i) By drawing tangents on the graphs, measure and calculate the initial rates of
reaction during the two runs. Give the units in each case.
initial rate of run A ....................................................................................................

initial rate of run B ....................................................................................................
[3]
(ii) By using your results, calculate the overall order of reaction with respect to [OH–].
............................................................................................................................ [1]
(iii) From the curve of run B, determine the order of reaction with respect to [ester].
............................................................................................................................ [1]
(iv) Explain how you arrived at you answer in (iii).
..................................................................................................................................
............................................................................................................................ [1]
(v) Write a rate equation for the reaction.
............................................................................................................................ [1]
(vi) Use your rate equation and the initial rates to calculate a value for the rate
constant, including units.
..................................................................................................................................
............................................................................................................................ [2]
[Total: 13]

6 For
Examiner's
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3 (a) Write an equation to represent the thermal decomposition of calcium nitrate, Ca(NO3)2.
.................................................................................................................................... [1]
(b) Describe and explain how the thermal stabilities of the Group II nitrates vary down the
group.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [3]
(c) When a molten nitrate of a Group I metal is heated strongly, it evolves oxygen and
leaves the metal nitrite, MNO2 (M = Na, K, Rb or Cs).
(i) Write a balanced equation for this reaction.
..................................................................................................................................
(ii) When a particular Group I metal nitrate was heated in this way until no further
change occurred, it lost 10.85% of its mass. Calculate the Ar of the metal and
hence identify it.
[3]
[Total: 7]
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4 (a) Complete the electronic configuration of the Fe3+ ion.
1s2 2s2 2p6 3s2 3p6 .................................................................................................... [1]
(b) By quoting suitable data from the Data Booklet, explain how E –o values can be used to
show the relative oxidising abilities of
(i) the halogens Cl2, Br2, I2,
..................................................................................................................................
..................................................................................................................................
(ii) the transition metal ions Cr3+, Fe3+, Co3+.
..................................................................................................................................
..................................................................................................................................
[3]
(c) Use these E –o values to predict whether a reaction will occur when the following pairs
of aqueous solutions are mixed. If a reaction occurs, write a balanced equation and
calculate the E –o cell.
(i) Fe3+(aq) and Cl –(aq)
..................................................................................................................................
..................................................................................................................................
(ii) Co3+(aq) and Br–(aq)
..................................................................................................................................
..................................................................................................................................
(iii) Cr2+(aq) and I2(aq)
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 8]

8 For
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5 The common analgesic drug paracetamol has the following structure.
CH3CONH OH
(a) Name the two functional groups in the paracetamol molecule
.............................................................. and ........................................................... [2]
(b) Draw the structural formulae of the molecules or ions formed when paracetamol reacts
with
(i) Br2(aq),
(ii) NaOH(aq) in the cold,
(iii) NaOH(aq) under reflux.
[3]
(c) Paracetamol can be synthesised by reacting 4-aminophenol with compound X.
H2N OH + X paracetamol
(i) Suggest a possible identity of X.
..................................................................................................................................
(ii) What reagent would you use to convert ethanoic acid, CH3CO2H, into X?
..................................................................................................................................
[2]
[Total: 7]
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6 Methylbenzene can react with chlorine in two ways, depending on the conditions of the
reaction.
CH3 CH3 CH2Cl

Cl2 Cl2
reaction I reaction II
Cl
A B
(a) State the condition needed for

(i) reaction I,
..................................................................................................................................
(ii) reaction II.
..................................................................................................................................
[2]
(b) One of the two compounds A and B reacts with NaOH(aq), but the other is inert.
(i) Which one (A or B) does not react? Give a reason for your answer.
..................................................................................................................................
..................................................................................................................................
(ii) Write an equation for the reaction with NaOH(aq) that does occur.
[2]
[Total: 4]

10 For
Examiner's
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7 Phenylamine is an important intermediate compound for the production of dyes.
NH2
phenylamine
(a) Phenylamine can be synthesised from benzene in two steps. Draw the structural formula
of the intermediate Y in the scheme below, and suggest reagents and conditions for
steps I and II.
I II
—NH2
reagent + conditions for step I .........................................................................................
reagent + conditions for step II ........................................................................................

[4]
(b) Phenylamine is a weak base.

(i) Write an equation showing phenylamine acting as a base.
(ii) How would you expect its basicity to compare with that of ammonia?
..................................................................................................................................
(iii) Explain the reasoning for your answer in (ii).
..................................................................................................................................
..................................................................................................................................
[3]
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(c) Dyes can be made from phenylamine by first converting it into benzenediazonium
chloride, and then coupling this with a phenol.
III IV
NH2 N2+Cl – dye
+ a phenol
(i) State the reagents and condition needed for step III.
..................................................................................................................................
(ii) What reagent is the phenol dissolved in for step IV to be effective?
..................................................................................................................................
(iii) Suggest the structural formula of the dye formed when benzenediazonium
chloride is coupled with 2-methylphenol.
[4]
[Total: 11]
9701/4/S02
12
BLANK PAGE
9701/4/S02
Centre Number Candidate Number Name

General Certificate of Education
Advanced Subsidiary Level and Advanced Level
CHEMISTRY 9701/04
Paper 4 Structured Questions
May/June 2003
1 hour
Candidates answer on the Question Paper.
Additional Materials:
Data Booklet
READ THESE INSTRUCTIONS FIRST
Write your name, Centre number and candidate number in the spaces provided at the top of this page.
Write in dark blue or black pen in the spaces provided on the Question Paper.
You may use a pencil for any diagrams, graphs, or rough working.
Do not use staples, paper clips, highlighters, glue or correction fluid.

For Examiner’s Use

1
3
If you have been given a label, look at the
details. If any details are incorrect or 4
missing, please fill in your correct details
in the space given at the top of this page. 5
Stick your personal label here, if 6

provided.
TOTAL
This document consists of 12 printed pages.

SP (NF/KN) S33030/4
© CIE 2003 [Turn over
www.xtremepapers.net
2 For
Examiner’s
Use
Answer all the questions in the spaces provided.
1 (a) What do you understand by the term standard electrode potential?
..........................................................................................................................................
......................................................................................................................................[2]
(b) The following cell was set up between a copper electrode and an unknown metal
electrode M 2+(aq) / M(s). The standard cell potential was found to be 0.76 V, and the
copper foil was the positive electrode.
direction of electron flow
copper foil
unknown metal
wire, M
M 2+(1 mol dm–3) CuSO4(1 mol dm–3)
(i) Use the Data Booklet to calculate the standard electrode potential of the
M 2+(aq) / M(s) system.
...................................................................................................................................
(ii) Draw an arrow over the voltmeter symbol in the above diagram to show the
direction of electron flow through the voltmeter.
(iii) Predict the outcomes of the following situations. Describe what you might see and
write ionic equations for any reactions that occur.
I A rod of metal M is dipped into a solution of 1 mol dm–3 CuSO4.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
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II Dilute sulphuric acid is added to a beaker containing a powdered sample of metal
M.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[6]
(c) Because of its increased scarcity, cheaper copper ornaments are no longer made from
the solid metal, but from iron that has been copper plated.
(i) Complete the following diagram showing the set-up for a copper electroplating
process. Show clearly the polarity (+/–) of the power source, and suggest a suitable
electrolyte.
d.c. source
object to be plated
electrolyte:
(ii) A current of 0.500 A is passed through the electroplating cell. Calculate the time
required to deposit a mass of 0.500 g of copper on to the ornament.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[5]
[Total : 13]
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2 (a) Barium ions are poisonous. Patients with digestive tract problems are sometimes given
an X-ray after they have swallowed a ‘barium meal’, consisting of a suspension of
BaSO4 in water. The [Ba2+(aq)] in a saturated solution of BaSO4 is too low to cause
problems of toxicity.
(i) Write an expression for the solubility product, Ksp, for BaSO4, including its units.
...................................................................................................................................
(ii) The numerical value of Ksp is 1.30 × 10–10. Calculate [Ba2+(aq)] in a saturated
solution of BaSO4.
...................................................................................................................................
...................................................................................................................................
(iii) The numerical value of Ksp for BaCO3 (5 × 10–10) is not significantly higher than
that for BaSO4, but barium carbonate is very poisonous if ingested. Suggest a
reason why this might be so.
...................................................................................................................................
...................................................................................................................................
[3]
(b) A useful commercial source of magnesium is sea water, where [Mg2+(aq)] is

0.054 mol dm–3. The magnesium is precipitated from solution by adding calcium
hydroxide.
Mg2+(aq) + Ca(OH)2(s) → Ca2+(aq) + Mg(OH)2(s)
(i) Write an expression for the Ksp of Mg(OH)2, including its units.
...................................................................................................................................
(ii) The numerical value for Ksp is 2.00 x 10–11. Calculate [Mg2+(aq)] in a saturated
solution of Mg(OH)2.
...................................................................................................................................
...................................................................................................................................
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(iii) Hence calculate the maximum percentage of the original magnesium in the
seawater that this method can extract.
...................................................................................................................................
...................................................................................................................................
[5]
(c) The magnesium ions in seawater are mainly associated with chloride ions.
__ __
(i) Use the following ∆H fo values to calculate a value for the ∆H o of the following
reaction.
MgCl2(s) → Mg2+(aq) + 2Cl –(aq)
__
species ∆H fo /kJ mol–1
MgCl2 (s) –641
Mg2+(aq) –467
Cl – (aq) –167
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) Use your answer to explain why MgCl2 is very soluble in water.
...................................................................................................................................
[2]
(d) All the chlorides of Group II elements are soluble in water. The same is not true of their
sulphates. These become less soluble as the group is descended.
Explain qualitatively the variation in solubility of the sulphates of the elements in

Group II down the Group from magnesium to barium.
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[2]
[Total : 12]
6 For
Examiner’s
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3 (a) The melting points of some oxides of Group IV elements are given below.
oxide melting
point / oC
CO2 –78
SiO2 1610
SnO2 1630
Describe the bonding in each oxide, and how it relates to its melting point.
(i) CO2
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) SiO2
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(iii) SnO2
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[3]
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(b) Writing balanced equations where appropriate, describe how the above three oxides
differ in their reactions with
(i) NaOH(aq),
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) HCl(aq).
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[4]
(c) The last oxide in Group IV, PbO2, reacts with concentrated hydrochloric acid liberating
chlorine gas.
o __
Use the Data Booklet to calculate the E cell and to write a balanced equation for this
reaction.
..........................................................................................................................................
......................................................................................................................................[2]
[Total : 9]
8 For
Examiner’s
Use
4 Chloroacetophenone (compound D, below) was formerly the most widely used tear gas,
under the codename CN. It was used in warfare and in riot control. It can be synthesised
from ethylbenzene, A, by the following route.
I II III IV
CH2CH3 CHClCH3 CH(OH)CH3 COCH3 COCH2Cl
A B C D
(a) Suggest reagents and conditions for step I.
......................................................................................................................................[1]
(b) Suggest reagents and conditions for converting ethylbenzene into compound E, an
isomer of B.
Cl CH2CH3
......................................................................................................................................[1]
(c) Draw the structure of the product obtained by heating ethylbenzene with KMnO4.
[1]
(d) Describe a test (reagents and observations) that would distinguish compound C from
compound F.
COCH2CH3
reagents
..........................................................................................................................................
observation with C
..........................................................................................................................................
observation with F
..........................................................................................................................................
[2]
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9 For
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(e) The efficiency of a tear gas is expressed by its ‘intolerable concentration’, I.C. The I.C.
of the tear gas CN has been measured as 0.030 g m–3 of air.
How many moles of chloroacetophenone need to be sprayed into a room of volume
60 m3 in order to achieve this concentration?
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[2]
(f) Residues of CN can be destroyed by hydrolysis with an aqueous alkali.
COCH2Cl + OH– COCH2OH + Cl–
Compounds G and H are isomers of compound D.
CH2COCl Cl COCH3
G H
(i) Arrange the three isomers D, G and H in order of increasing ease of hydrolysis.
...................................................................................................................................
(ii) Explain the reasoning behind your choice.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[3]
[Total : 10]
10 For
Examiner’s
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5 (a) Acyl chlorides are useful intermediates for making various acid derivatives. The
following reaction scheme shows some of the reactions of ethanoyl chloride.
step I OH + NaOH(aq)
CH3CO2H CH3COCl
step II
step III NH3

J
(i) Suggest a reagent for step I.
...................................................................................................................................
(ii) Write an equation showing the reaction between phenol and NaOH(aq), the
reagents in step II.
...................................................................................................................................
(iii) Draw the structural formulae of products J and K in the boxes above.
[4]
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(b) The diacid L occurs naturally and is used as a food additive to enhance the acidic
flavour in some fruit drinks.
HO2CCH2CH2CO2H
L
When the diacyl chloride of L is reacted with HOCH2CH2OH, a polymer is formed.
(i) What type of polymerisation is occurring here?
...................................................................................................................................
(ii) Write an equation showing the reaction between one mole of the diacyl chloride of
L and two moles of HOCH2CH2OH.
[3]
(c) The following formula represents a section of another polymer.
CO CONHCH2CH2CH2CH2NH
(i) What type of polymer is this?
...................................................................................................................................
(ii) Draw the structural formula of each of the monomers that make up this polymer.
[3]
[Total : 10]
12 For
Examiner’s
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6 (a) Titanium is an important transition metal. The metal itself is a component of many high-
strength low-weight alloys, and its oxide is used as an opaque agent in many paints
and pigments.
(i) Write out the electronic configuration of the titanium atom.
...................................................................................................................................
(ii) Titanium forms two chlorides. Suggest possible formulae for them.
...................................................................................................................................
[2]
(b) Anhydrous copper sulphate, CuSO4(s), is a white powder that readily dissolves in water.
(i) Describe and explain what is seen when CuSO4(s) is stirred with water.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) Describe and explain the final colour change seen when an excess of NH3(aq) is
added to CuSO4(aq).
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[4]
[Total : 6]
9701/04/M/J/03
UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS

CHEMISTRY 9701/04
Paper 4 Structured Questions
May/June 2004
1 hour 15 minutes
Additional Materials: Data Booklet
Write your Centre number, candidate number and name on all the work you hand in.

You may use a calculator.

1
3

provided.
Total
This document consists of 11 printed pages and 1 blank page.

SP (NF/GR) S60728/4
© UCLES 2004 [Turn over
2 For
Examiner’s
Use
1 Magnesium is used extensively in the form of alloys as a constructional material due to its
low density (1.7 g cm–3, compared to 7.8 g cm–3 for iron). It is usually prepared by the
electrolysis of magnesium chloride, MgCl2, at a temperature a little above its melting point of
715 °C.
(a) Suggest the half-equation that represents the production of magnesium at the cathode
during the electrolysis.
......................................................................................................................................[1]
(b) What will be the product at the other electrode?
......................................................................................................................................[1]
(c) Suggest two properties of its atoms that could explain why magnesium is less dense
than iron.
..........................................................................................................................................
......................................................................................................................................[2]
One of the reasons the melting point of magnesium chloride is quite high is because it has a
fairly high lattice energy.
(d) (i) Explain the term lattice energy.
...................................................................................................................................
...................................................................................................................................
(ii) Write a balanced equation including state symbols to represent the lattice energy
of magnesium chloride.
...................................................................................................................................
...............................................................................................................................[4]
(e) Suggest, with an explanation in each case, how the lattice energy of magnesium
chloride might compare with that of
(i) sodium chloride, NaCl,
...................................................................................................................................
...................................................................................................................................
(ii) calcium chloride, CaCl2.
...................................................................................................................................
...............................................................................................................................[4]
© UCLES 2004 9701/04/M/J/04
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(f) Use the following data to calculate a value for the lattice energy of sodium chloride.
∆Hf (NaCl) = – 411 kJ mol–1

∆Hat (Na) = 107 kJ mol–1
∆Hat (Cl) = 122 kJ mol–1
first ionisation energy of Na = 494 kJ mol–1
electron affinity of Cl = – 349 kJ mol–1
lattice energy of NaCl = ........................................ kJ mol–1 [3]
[Total: 15]
© UCLES 2004 9701/04/M/J/04 [Turn over
4 For
Examiner’s
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2 All the Group IV elements form chlorides with the formula MCl4.
(a) Describe the bonding in, and the shape of, these chlorides.
(i) bonding .....................................................................................................................
(ii) shape ....................................................................................................................[2]
The boiling point of lead(IV) chloride cannot be measured directly because it decomposes
on heating. The following table lists the boiling points of three Group IV chlorides.
chloride b.p. / °C
SiCl4 58
GeCl4 83
SnCl4 114
(b) (i) Plot these data on the following axes and extrapolate your graph to predict what the
boiling point of PbCl4 would be if it did not decompose.
150°C
100°C
50°C
Si Ge Sn Pb
(ii) Suggest why the boiling points vary in this way.
...................................................................................................................................
...................................................................................................................................
...............................................................................................................................[4]
© UCLES 2004 9701/04/M/J/04
5 For
Examiner’s
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(c) SiCl4 reacts vigorously with water whereas CCl4 is inert.
(i) Suggest a reason for this difference in reactivity.
...................................................................................................................................
(ii) Write an equation for the reaction between SiCl4 and water.
...................................................................................................................................
(iii) Suggest, with a reason, whether you would expect GeCl4 to react with water.
...................................................................................................................................
...................................................................................................................................
[3]
(d) SiCl4 is used to make high-purity silicon for the semiconductor industry. After it has
been purified by several fractional distillations, it is reduced to silicon by heating with
pure zinc.
(i) Suggest an equation for the reduction of SiCl4 by zinc.
...................................................................................................................................
(ii) Use your equation to calculate what mass of zinc is needed to produce 250 g of
pure silicon by this method.
mass of zinc = ....................... g [3]
[Total: 12]
6 For
Examiner’s
Use
3 By using iron and its compounds as examples, outline the different modes of action of
homogeneous and heterogeneous catalysis.
Choose two examples, and for each example you should
• state what the catalyst is, and whether it is acting as a homogeneous or a
heterogeneous catalyst,
• write a balanced equation for the reaction.
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..............................................................................................................................................[8]
[Total: 8]
© UCLES 2004 9701/04/M/J/04
7 For
Examiner’s
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4 This question is about the reactions of some functional groups.
(a) (i) Draw the structural formula of an amide of your choice containing four carbon
atoms.
(ii) What reagents and conditions are needed to hydrolyse this amide?
...................................................................................................................................
(iii) Write a balanced equation showing the hydrolysis of the amide whose structural
formula you drew in part (i).
...............................................................................................................................[4]
(b) (i) Draw the structural formula of an acyl chloride containing three carbon atoms.
(ii) What starting material and reagent are needed to form this acyl chloride?
...................................................................................................................................
(iii) Write a balanced equation showing the formation of an ester containing five carbon
atoms from the acyl chloride you drew in part (i).
...............................................................................................................................[3]
[Total: 7]
8 For
Examiner’s
Use
5 (a) State the reagents and conditions needed to convert benzene into
(i) chlorobenzene,
...................................................................................................................................
(ii) bromobenzene,
...................................................................................................................................
(iii) nitrobenzene.
...................................................................................................................................
[4]
(b) The nitration of benzene is a two-step reaction that can be represented as follows.
+ +
+ A NO2 + H
(i) Identify the cation A+. ...............................................................................................

(ii) Draw the structure of the intermediate B in the box. [2]
© UCLES 2004 9701/04/M/J/04
9 For
Examiner’s
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(c) The position of substitution during the electrophilic substitution of arenes is determined
by the nature of the group already attached to the ring.
Electron-withdrawing groups such as –CO2H or –NO2 direct the incoming group to the
3-position.
CO2H CO2H
nitration
NO2
On the other hand, electron-donating groups such as –CH3 or –NH2 direct the incoming
group to the 2- or 4- positions.
CH3 CH3 CH3

Br
bromination +
Br
Use this information to suggest a likely structure for the organic product of each of the
following reactions.
(i)
NO2
bromination
(ii)
NH2
chlorination
CO2H
[2]
[Total: 8]
10 For
Examiner’s
Use
6 Much research has been carried out in recent years investigating the exact structure of silk.
The silk of a spider’s web is at least five times as strong as steel, and twice as elastic as
nylon. A silk fibre is composed of many identical protein chains, which are mainly made from
the amino acids glycine, alanine and serine, with smaller amounts of four other amino acids.
NH2–CH2–CO2H NH2–CH–CO2H NH2–CH–CO2H

| |
CH3 CH2OH
glycine alanine serine
(a) Amino acids can exist as zwitterions. Draw the zwitterionic structure for glycine.
[1]
(b) Amino acids can act as acids or bases. Write equations to show:
(i) the reaction between alanine and HCl(aq),
...................................................................................................................................
(ii) the reaction between serine and NaOH(aq).
...................................................................................................................................
[2]
(c) Draw the structural formula of a portion of the silk protein, showing three amino acid
residues. Label a peptide bond on your structure.
[3]
(d) What type of polymer is silk protein?
......................................................................................................................................[1]
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(e) The Mr of a silk protein molecule is about 600,000. Assuming it is made from equal
amounts of the above three amino acids, calculate the average number of amino acid
residues in the protein chain. [Mr (glycine) = 75; Mr (alanine) = 89; Mr (serine) = 105]
number of residues = ................................... [3]
[Total: 10]
© UCLES 2004 9701/04/M/J/04
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BLANK PAGE
University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of
the University of Cambridge.
9701/04/M/J/04

CHEMISTRY 9701/04
Paper 4 Structured Questions A2 Core
May/June 2005
1 hour 15 minutes

A Data Booklet is provided.

1
3

provided.
TOTAL

SPA (MML 8078 3/04) S77899/2
2 For
Examiner's
Use
1 A student decided to determine the value of the Faraday constant by an electrolysis

experiment. The following incomplete diagram shows the apparatus that was used.
hydrogen
being
collected
dilute H2SO4 power pack

–
inert electrodes
(a) (i) Apart from connecting wires, what two additional pieces of equipment are needed
for this experiment?
..................................................................................................................................
..................................................................................................................................
(ii) Complete the diagram, showing additional equipment connected in the circuit, and
showing the powerpack connected to the correct electrodes.
(iii) List the measurements the student would need to make in order to use the results
to calculate a value for the Faraday constant.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[7]
(b) (i) Using an equation, state the relationship between the Faraday constant, F, the
Avogadro constant, L, and the charge on the electron, e.
..................................................................................................................................
(ii) The value the student obtained was: 1 Faraday = 9.63 × 104 Coulombs
Use this value and your equation in (b)(i) to calculate the Avogadro constant (take
the charge on the electron to be 1.60 × 10–19 Coulombs)
..................................................................................................................................
..................................................................................................................................
[2]
[Total: 9]
© UCLES 2005 9701/04/M/J/05
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Examiner's
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2 (a) What do you understand by the term order of reaction?
.................................................................................................................................... [1]
(b) Cyanohydrins can be made by reacting ketones with an acidified solution of sodium
cyanide.
(CH3)2C=O + H+ + CN– → (CH3)2C(OH)CN
In a series of experiments, the reaction was carried out with different concentrations of
the three reagents, and the following relative initial rates were obtained.
experiment [(CH3)2CO] [H+] [CN–] relative initial rate /

number / mol dm–3 / mol dm–3 / mol dm–3 mol dm–3 sec–1
1 0.020 0.060 0.060 1.00
2 0.020 0.050 0.050 0.833
3 0.020 0.050 0.060 1.00
4 0.025 0.050 0.050 1.042
(i) Use the data in the table to deduce the order of the reaction with respect to
propanone ....................................................
hydrogen ions ..............................................
cyanide ions .................................................

(ii) Hence write a rate equation for this reaction.
..................................................................................................................................
Two different mechanisms have been suggested for this reaction
Mechanism A: (CH3)2C=O + H+ → (CH3)2COH+

(CH3)2COH+ + CN– → (CH3)2C(OH)CN
Mechanism B: (CH3)2C=O + CN– → (CH3)2C(O–)CN

(CH3)2C(O–)CN + H+ → (CH3)2C(OH)CN
(iii) Which mechanism is consistent with the rate equation you deduced in (ii), and
which step in this mechanism is the slower (rate determining) step? Explain your
answer.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[7]
[Total: 8]
4 For
Examiner's
Use
3 Limestone is an important raw material, used in building, steel making and agriculture.
The first stage in using limestone is often to heat it in a kiln.
CaCO3(s) → CaO(s) + CO2(g) H = +178 kJ mol–1 reaction 1
Water is then added to the ‘quicklime’ produced in the kiln, to make ‘slaked lime’.
CaO(s) + H2O(l) → Ca(OH)2(s) H = – 82 kJ mol–1 reaction 2
(a) (i) Suggest two reasons why reaction 1 needs heating to a high temperature.
..................................................................................................................................
..................................................................................................................................
(ii) Explain whether MgCO3 would require a higher or a lower temperature than
CaCO3 for its decomposition.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[5]
Before the widespread use of cement, bricks and stones used for buildings were bonded
together with a mixture of slaked lime, sand and water, known as lime mortar. On exposure
to the air, the lime mortar gradually set hard due to the following reaction.
Ca(OH)2(s) + CO2(g) → CaCO3(s) + H2O(l)
(b) Use the data given above to calculate the enthalpy change for this reaction.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [1]
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(c) One of the major ores of magnesium is the mixed carbonate called dolomite,
CaMg(CO3)2.
Calculate the percentage loss in mass that would be observed when a sample of
dolomite is heated at a high temperature until the reaction had finished.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
[Total: 8]
6 For
Examiner's
Use
4 (a) (i) State the electronic configuration of the iron atom.
..................................................................................................................................
(ii) Apart from its electronic structure, state two properties of iron or its compounds
that are characteristic of a transition element.
..................................................................................................................................
..................................................................................................................................
[3]
(b) Acidified solutions of iron(II) salts can be titrated using a dilute solution of potassium
manganate(VII), KMnO4.
(i) Use the Data Booklet to calculate the standard cell potential and to write a
balanced ionic equation for the reaction that takes place during the titration.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Explain why no indicator is required for this titration. What colour change would
you see at the end point?
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
(c) Use the reaction between Fe3+ ions and water molecules to explain the meanings of
the terms ligand and complex formation.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
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(d) An important biological molecule containing iron is haemoglobin.
(i) What is the role of haemoglobin in the body?
..................................................................................................................................
(ii) Use your answer to (i) to explain why carbon monoxide is poisonous.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[2]
(e) In a possible industrial synthesis of ethanol, the complex Fe(CO)5 catalyses the
reaction between carbon monoxide, hydrogen and methanol according to the following
equation.
200 °C
CH3OH + 2CO + H2 –––––→ CH3CH2OH + CO2
300 atm
Describe a test (reagents and observations) that would distinguish ethanol from
methanol.
reagents ...........................................................................................................................
observation with methanol ...............................................................................................
observation with ethanol ............................................................................................. [2]

[Total: 13]
8 For
Examiner's
Use
5 (a) Give an expression for Ka as applied to the weak acid RCO2H.
..........................................................................................................................................
.................................................................................................................................... [1]
(b) The Ka values for three carboxylic acids are listed in the table below.
acid Ka / mol dm–3
CH3CO2H 1.8 × 10–5
ClCH2CO2H 1.4 × 10–3
Cl2CHCO2H 5.5 × 10–2
(i) Describe and explain the trend in acid strength illustrated by these values.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Calculate the pH of a 0.100 mol dm–3 solution of ClCH2CO2H.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) Calculate the pKa value for Cl 2CHCO2H.
..................................................................................................................................
..................................................................................................................................
[5]
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(c) The acid ClCH2CO2H features in the industrial synthesis of the important weedkiller
2,4-D.
OH OH OCH2CO2H
Cl Cl
I II
+ NaOH
+ ClCH2CO2H
phenol
Cl Cl
2,4-D
(i) Suggest a possible reagent for reaction I.
..................................................................................................................................
(ii) What type of reaction is
reaction I, .................................................................................................................
reaction II? ...............................................................................................................

(iii) Describe a test (reagents and observations) that would distinguish phenol from
compound A.
CH2OH
compound A
reagents ...................................................................................................................
observation with phenol ...........................................................................................
observation with compound A ..................................................................................

[5]
[Total: 11]
10 For
Examiner's
Use
6 The antipyretic (fever-reducing) drug antifebrin can be made from benzene and ethanoic
acid by the following route.
NO2 NH2
I II
NHCOCH3
IV
III
CH3CO2H CH3COCl antifebrin
(a) (i) What type of reaction is reaction I?
..................................................................................................................................
(ii) Suggest the reagents and conditions for reaction I.
..................................................................................................................................
(iii) Complete the following scheme showing the mechanism of reaction I, by drawing
appropriate formulae in the three boxes.
NO2
+ +
[6]
(b) (i) What type of reaction is reaction II?
..................................................................................................................................
(ii) Suggest the reagents and conditions for reaction II.
..................................................................................................................................
[2]
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(c) Suggest the reagents and conditions for reaction III.
.................................................................................................................................... [1]
(d) (i) Apart from the benzene ring, name the functional group in antifebrin.
..................................................................................................................................
(ii) What reagents and conditions are needed to hydrolyse antifebrin?
..................................................................................................................................
[2]
[Total: 11]
© UCLES 2005 9701/04/M/J/05
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Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every
reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the
publisher will be pleased to make amends at the earliest possible opportunity.
University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department
of the University of Cambridge.
9701/04/M/J/05

CHEMISTRY 9701/04
May/June 2006
1 hour 15 minutes
You may use a pencil for any diagrams, graphs or rough working.

At the end of the examination, fasten all your work securely together.

1
Total

SPA SJF3704 T12878/2
2 For
Examiner’s
Use
1 The oxidation of nitrogen monoxide occurs readily according to the following equation.
NO(g) + O2(g) ⎯→ NO2(g)
The following table shows how the initial rate of this reaction depends on the concentrations
of the two reactants.
[NO] [O2] initial rate

/ mol dm–3 / mol dm–3 / mol dm–3 s–1
0.0050 0.0050 0.02
0.0050 0.0075 0.03
0.010 0.0075 0.12
(a) (i) Use the data to determine the order of reaction with respect to each of the
reagents.
order with respect to NO …………………………
order with respect to O2 …………………………
(ii) Write the rate equation for the reaction, and use it to calculate a value for the rate
constant, k, stating its units.
rate equation .............................................................................................................
numerical value of k = …………………………
units of k …………………………
(iii) Use your rate equation in (ii) to calculate the rate of reaction when
[NO] = [O2] = 0.0025 mol dm–3.
rate of reaction =…………………………

[6]
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(b) Nitrogen monoxide plays an important catalytic role in the oxidation of atmospheric SO2
in the formation of acid rain.
(i) State the type of catalysis shown in this process.
...................................................................................................................................
(ii) Explain the steps involved in this process by writing equations for the reactions that
occur.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[3]
[Total: 9]
4 For
Examiner’s
Use
2 Monuments made of marble or limestone, such as the Taj Mahal in India and the Mayan
temples in Mexico, are suffering erosion by acid rain. The carbonate stone is converted by
the acid rain into the relatively more soluble sulphate.
CaCO3(s) + H2SO4(aq) → CaSO4(s) + H2O(l) + CO2(g)

acid rain
(a) (i) Write an expression for the solubility product, Ksp, of CaSO4, stating its units.
...................................................................................................................................
(ii) The Ksp of CaSO4 has a numerical value of 3 x 10–5. Use your expression in (i) to
calculate [CaSO4] in a saturated solution.
...................................................................................................................................
(iii) Hence calculate the maximum loss in mass of a small statue if 100 dm3 of acid rain
falls on it. Assume the statue is made of pure calcium carbonate, and that the acid
rain becomes saturated with CaSO4.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[5]
(b) The life of such monuments is now being extended by treating them with a mixture of
urea and barium hydroxide solutions. After soaking into the pores of the carbonate rock,
the urea gradually decomposes to ammonia and carbon dioxide. The carbon dioxide
then reacts with the barium hydroxide to form barium carbonate.
(NH2)2CO(aq) + H2O(l) ⎯→ 2NH3(g) + CO2(g)
Ba(OH)2(aq) + CO2(g) ⎯→ BaCO3(s) + H2O(l)
Acid rain then converts the barium carbonate to its sulphate.
BaCO3(s) + H2SO4(aq) ⎯→ BaSO4(s) + H2O(l) + CO2(g)
Barium sulphate is much less soluble than calcium sulphate. A saturated solution
contains [Ba2+] = 9.0 x 10–6 mol dm–3.
(i) Explain why barium sulphate is less soluble than calcium sulphate.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
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(ii) Write an expression for the Ksp of barium sulphate and use the data to calculate its
value.
...................................................................................................................................
...................................................................................................................................
[4]
(c) (i) Explain what is meant by the term lattice energy.
...................................................................................................................................
...................................................................................................................................
(ii) Predict, with a reason, how the lattice energy of BaSO4 might compare with that of
MgSO4.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[3]
[Total: 12]
6 For
Examiner’s
Use
3 (a) A transition element X has the electronic configuration [Ar] 4s2 3d3.
(i) Predict its likely oxidation states.
...................................................................................................................................
(ii) State the electronic configuration of the ion X3+.
...................................................................................................................................
[2]
(b) Potassium manganate(VII), KMnO4, is a useful oxidising agent in titrimetric analysis.
(i) Describe how you could use a 0.0200 mol dm–3 solution of KMnO4 to determine
accurately the [Fe2+] in a solution. Include in your description how you would
recognise the end-point in the titration, and write an equation for the titration
reaction.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) A 2.00 g sample of iron ore was dissolved in dilute H2SO4 and all the iron in the
salts produced was reduced to Fe2+(aq). The solution was made up to a total
volume of 100 cm3.
A 25.0 cm3 portion of the solution required 14.0 cm3 of 0.0200 mol dm–3 KMnO4 to
reach the end-point.
Calculate the percentage of iron in the ore.
...................................................................................................................................
[8]
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Use
(c) High-strength low-alloy (HSLA) steels are used to fabricate TV masts and long span
bridges. They contain very low amounts of phosphorus and sulphur, but about 1%
copper, to improve resistance to atmospheric corrosion. When dissolved in nitric acid, a
sample of this steel gives a pale blue solution.
(i) What species is responsible for the pale blue colour?
...................................................................................................................................
(ii) Describe and explain what you would see when dilute aqueous ammonia is added
to this solution.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[4]
[Total: 14]
8 For
Examiner’s
Use
4 The amino acids tyrosine, lysine and glycine are constituents of many proteins.
H 2N CH C OH
O
CH2
H2N CH C OH O
(CH2)4 H2N CH C OH
NH2 H
OH
tyrosine lysine glycine
(a) State the reagents and conditions you could use to break proteins down into amino
acids.
..................................................................................................................................... [2]
(b) Draw a ring around each chiral centre in the above molecules. [1]
(c) In aqueous solution amino acids exist as zwitterions. Draw the zwitterionic structure of
glycine.
..................................................................................................................................... [1]
(d) For each of the following reactions, draw the structure of the organic compound formed.
(i) glycine + excess NaOH(aq)
...................................................................................................................................
(ii) tyrosine + excess NaOH(aq)
...................................................................................................................................
© UCLES 2006 9701/04/M/J/06
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Examiner’s
Use
(iii) lysine + excess HCl (aq)
...................................................................................................................................
(iv) tyrosine + excess Br2(aq)
...................................................................................................................................
[5]
(e) Draw the structural formula of a tripeptide formed from all three of these amino acids,
showing clearly the peptide bonds.
..................................................................................................................................... [2]
(f) The formula of part of the chain of a synthetic polyamide is shown below.
CH2 NH CO CO NH CH2 CH2 NH CO CO NH CH2 CH2 NH
(i) Identify the repeat unit of the polymer by drawing square brackets around it on the
above formula.
(ii) Draw the structures of the two monomers from which the polymer could be made.
...................................................................................................................................
[3]
[Total: 14]
10 For
Examiner’s
Use
5 Benzocaine is an important local anaesthetic used in skin creams for sprains and other
muscular pains. It can be made by the following route.
CH3 CH3 CO2H CO2H CO2CH2CH3
I II III IV
NO2 NO2 NH2 NH2
benzocaine
(a) Suggest reagents and conditions for each of the above four reactions.
I ...................................................................................................................................
II ...................................................................................................................................
III ...................................................................................................................................
IV .............................................................................................................................. [6]
(b) Draw steps to show the mechanism of reaction I.
[2]
(c) Another local anaesthetic is amylocaine, which can be made from compound X.
O O CH3
C CH2 NH2 C CH2 N
O C O C CH3
CH3 CH3
CH2CH3 CH2CH3
X amylocaine
(i) Apart from the benzene ring, name two functional groups in the molecule of
compound X.
...................................................................................................................................
...................................................................................................................................
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(ii) Explain whether compound X would be more or less basic than benzocaine.
...................................................................................................................................
...................................................................................................................................
[3]
[Total: 11]
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9701/04/M/J/06
General Certificate of Education Advanced Subsidiary Level and Advanced Level
*6631076049*
CHEMISTRY 9701/04
Paper 4 Structured Questions May/June 2007
1 hour 45 minutes
Write in dark blue or black pen.
Do not use staples, paper clips, highlighters, glue or correction fluid
DO NOT WRITE IN ANY BARCODES.
Section A
Section B
Answer all questions. For Examiner’s Use
You may lose marks if you do not show your working or if you do not use 1
appropriate units.
A Data Booklet is provided. 2
At the end of the examination, fasten all your work securely together. 3
The number of marks is given in brackets [ ] at the end of each question or
4
part question.
5
Total
SP (KN) T32180/4
2 For
Examiner’s
Use
Section A
Answer all questions in the spaces provided.
1 Zinc chloride is one of the most important compounds of zinc. It is used in dry cell batteries,
as a flux for soldering and tinning, as a corrosion inhibitor in cooling towers and in the
manufacture of rayon.
(a) Draw a fully labelled diagram to show how you could use a standard hydrogen electrode
to measure the standard electrode potential, E o, of zinc.
[6]
(b) The electrolysis of zinc chloride can give different electrode products, depending on the
conditions used.
Suggest the products formed at each electrode in the following cases. One space has
been filled in for you.
conditions product at anode product at cathode
ZnCl2(l) chlorine
ZnCl2(concentrated aqueous)
ZnCl2(dilute aqueous)
[3]
(c) Use the following data, together with relevant data from the Data Booklet, to construct a
Born-Haber cycle and calculate a value for the lattice energy of zinc chloride.
standard enthalpy change of formation of ZnCl2 –415 kJ mol–1

standard enthalpy change of atomisation of Zn(s) +131 kJ mol–1
electron affinity per mole of chlorine atoms –349 kJ mol–1
lattice energy = ............................................... kJ mol–1 [3]
© UCLES 2007 9701/04/M/J/07
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Examiner’s
Use
(d) Zinc is an essential element for plant and animal life. It is often administered in the form
of a chelate, which is a complex between a metal ion and a polydentate ligand.
The rate of the reaction between zinc ions and the ligand 4-(2-pyridylazo)resorcinol,
PAR, has been studied.
HO HO
Zn2+ + 2 N N Zn2+ N N + 2H+

N N
–O
HO 2
PAR Zn-PAR
Both PAR and its zinc complex absorb radiation in the UV-visible region. The figure
below shows their absorption spectra.
1.4
1.2
1.0
absorbance
0.8
PAR
0.6 Zn-PAR
0.4
0.2
0.0
300 400 500 600 700
wavelength / nm
(i) Devise a suitable experimental technique for studying how the rate of this reaction
varies with [Zn2+(aq)].
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Describe a reaction you could carry out to show that PAR is a phenol.
..................................................................................................................................
..................................................................................................................................
[7]
[Total: 19]
4 For
Examiner’s
Use
2 (a) Write an equation showing the reaction that occurs when calcium nitrate, Ca(NO3)2, is
heated.
......................................................................................................................................[1]
(b) Describe and explain the trend in thermal stability of the nitrates of the Group II
elements.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(c) Gently heating ammonium nitrate, NH4NO3, in a test tube produces a mixture of two
gases A and B. No residue remains in the tube.
The mass spectrum of gas A contains peaks at m/e (mass number) values of 16, 17
and 18, whereas that of gas B has peaks at m/e values of 14, 16, 28, 30 and 44.
(i) Identify the peaks in the mass spectra, and suggest the molecular formulae of the
gases A and B.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Hence suggest an equation for the thermal decomposition of ammonium nitrate.
..................................................................................................................................
[5]
[Total: 9]
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5 For
Examiner’s
Use
3 Carbon forms two stable oxides, CO and CO2. Lead forms three oxides: yellow PbO, black
PbO2 and red Pb3O4.
(a) Carbon monoxide burns readily in air. Heating black lead oxide produces oxygen gas,
leaving a yellow residue.
(i) Suggest a balanced equation for each reaction.
..................................................................................................................................
..................................................................................................................................
(ii) Explain how these two reactions illustrate the relative stabilities of the +2 and +4
oxidation states down Group IV.
..................................................................................................................................
..................................................................................................................................
[3]
(b) Red lead oxide contains lead atoms in two different oxidation states.
(i) Suggest what these oxidation states are, and calculate the ratio in which they occur
in red lead oxide.
..................................................................................................................................
..................................................................................................................................
(ii) Predict the equation for the action of heat on red lead oxide.
..................................................................................................................................
When red lead oxide is heated with dilute nitric acid, HNO3, a solution of lead(II) nitrate
is formed and a black solid is left.
(iii) Suggest an equation for this reaction.
..................................................................................................................................
(iv) Explain how this reaction illustrates the relative basicities of the two oxidation states
of lead.
..................................................................................................................................
..................................................................................................................................
[5]
(c) Both tin(II) oxide and tin(IV) oxide are amphoteric.
Write a balanced equation for the reaction between tin(II) oxide and aqueous sodium
hydroxide.
......................................................................................................................................[1]
[Total: 9]
6 For
Examiner’s
Use
4 The following passage is taken from an A level Chemistry text book.
“In an isolated atom, the five d-orbitals have the same energy. In an octahedral complex ion, however,
the presence of the ligands splits the five orbitals into a group of three and a group of two. These two
groups have slightly different energies.”
(a) Use the following sets of axes to draw the shape of one d-orbital in each of the two
groups mentioned above.
[2]
(b) Explain how the presence of the six ligands, L, in [FeL6]3+ splits the 3d orbitals into two
groups of different energy, and explain whether the two-orbital group or the three-orbital
group has the higher energy.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
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Use
(c) The following table lists the colours and energies of photons of light of certain
wavelengths.
wavelength energy of colour of

/ nm photon photon
400 high violet
450 ↓ blue
500 lower green
600 ↓ yellow
650 low red
The visible spectra of solutions of two transition metal complexes C and D are shown in
the diagram below.
1.4
1.2
1.0
absorbance
0.8 D
C
0.6
0.4
0.2
0.0
300 400 500 600 700
wavelength / nm
(i) A list of possible colours for these complexes is as follows.
yellow red green blue
Choose one of these words to describe the observed colour of each solution.
solution C ............................................ solution D ................................................
(ii) In which complex, C or D, will the energy gap between the two groups of orbitals be
the larger? Explain your answer.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 8]
8 For
Examiner’s
Use
5 The following scheme shows some reactions of methylbenzene.
CH3 CH3 CH2Cl
I II
Cl III F
E
CO2H COCl
IV
(a) Suggest reagents and conditions for reactions I to IV.
I ........................................................................................................................................
II .......................................................................................................................................
III ......................................................................................................................................
IV .....................................................................................................................................
[4]
(b) What type of reaction is each of the following?
reaction I ..........................................................................................................................
reaction III ........................................................................................................................

[2]
© UCLES 2007 9701/04/M/J/07
9 For
Examiner’s
Use
(c) Compound F can be converted into 2-phenylethylamine in a two-stage process.
Suggest a structure for the intermediate, H, in the box below, and suggest reagents and
conditions for the steps V and VI.
CH2Cl CH2CH2NH2
V VI
F H
reagents and conditions for step V ..................................................................................
reagents and conditions for step VI .................................................................................

[4]
(d) The compounds E, F and G react at different rates with nucleophilic reagents. Draw
structures for the products of each compound with the following reagents.
If no reaction occurs, write “no reaction” in the box.
reagent
compound
cold water hot NaOH(aq)
[6]
[Total: 16]
10 For
Examiner’s
Use
6 Chemists use skeletal or partial-skeletal formulae to represent larger structures. For example
the structure
CH3 OH
CH2 H
C
H2C C
CH2
H2C CH
CH2
CH2
may also be represented as follows.
OH
CH3 H
Oestradiol is one of the hormones that controls the reproductive cycle in female mammals.
HO
CH3 H
H
H H
HO
oestradiol
(a) (i) On the above structure of oestradiol, circle one chiral centre.
(ii) What is the total number of chiral centres in the oestradiol molecule? .....................
[2]
(b) Complete the following part-structures (which have the -OH groups removed) to show
the products obtained when oestradiol (above) is reacted with the stated reagents.
(i) sodium metal
CH3
H
H H
© UCLES 2007 9701/04/M/J/07
11 For
Examiner’s
Use
(ii) Br2(aq)
CH3
H
H H
(iii) NaOH(aq)
CH3
H
H H
(iv) CH3COCl
CH3
H
H H
(v) hot acidified K2Cr2O7
CH3
H
H H
[7]
[Total: 9]
12 For
Examiner’s
Use
Section B – Applications of Chemistry
7 (a) (i) In a protein, amino acids are joined together by a process called condensation
polymerisation. Addition polymerisation is used in some synthetic polymers, such
as poly(propene).
State two important differences between condensation polymerisation and addition

polymerisation.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Using the amino acids glycine and alanine shown, draw the displayed formula of
the dipeptide ala-gly, clearly labelling the peptide link.
H H
H2N C CO2H H2N C CO2H
H CH3
glycine alanine
[4]
(b) The diagram below shows a section of DNA.

Identify the blocks labelled X, Y and Z.
X A Z X
Y Y
X C G X
Y Y
X C G X
Y Y
X ...................................... Y ...................................... Z ......................................

[3]
© UCLES 2007 9701/04/M/J/07
13 For
Examiner’s
Use
(c) The table below shows the 3-base codes used by RNA.
UUU phe UCU ser UAU tyr UGU cys

UUC phe UCC ser UAC tyr UGC cys
UUA leu UCA ser UAA stop UGA stop
UUG leu UCG ser UAG stop UGG trp
CUU leu CCU pro CAU his CGU arg

CUC leu CCC pro CAC his CGC arg
CUA leu CCA pro CAA gln CGA arg
CUG leu CCG pro CAG gln CGG arg
AUU ile ACU thr AAU asn AGU ser

AUC ile ACC thr AAC asn AGC ser
AUA ile ACA thr AAA lys AGA arg
AUG met/ ACG thr AAG lys AGG arg
start
GUU val GCU ala GAU asp GGU gly

GUC val GCC ala GAC asp GGC gly
GUA val GCA ala GAA glu GGA gly
GUG val GCG ala GAG glu GGG gly
(i) What amino acid sequence would the following base code produce?
(You may use abbreviations in your answer.)
-AUGUCUAGAGACGGGUAA-
..................................................................................................................................
..................................................................................................................................
(ii) What would be the effect on the amino acid sequence if a mutation caused the
base G at position 13 in the sequence to be replaced by U?
..................................................................................................................................
..................................................................................................................................
[3]
(d) (i) Name a disease which results from a genetic defect.
..................................................................................................................................
(ii) Explain how the genetic defect can bring about your named disease.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 13]
14 For
Examiner’s
Use
8 (a) Electrophoresis can be used to separate amino acids which are produced by the
hydrolysis of a polypeptide.
Using glycine as an example, explain why the result of electrophoresis depends on pH.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(b) The diagram below shows the results of electrophoresis in neutral solution. At the start
of the experiment a spot of a solution containing a mixture of amino acids P, Q, R and S
was placed in the middle of the plate. Following electrophoresis the amino acids had
moved to the positions shown in the lower diagram.
before + –
after + –
P Q R S
(i) Which amino acid existed mainly as a zwitterion in the buffer solution?
Explain your answer.
..................................................................................................................................
..................................................................................................................................
(ii) Assuming amino acids R and S carry the same charge when in this buffer solution,
which is likely to be the larger molecule? Explain your answer.
..................................................................................................................................
..................................................................................................................................
[2]
(c) Amino acids may also be separated by using two-dimensional paper chromatography.
This involves putting a spot of the mixture on the corner of a piece of chromatography
paper and allowing a solvent to soak up the paper. The paper is then dried, turned
through 90° and placed in a second solvent. This method gives better separation than a
one solvent method.
(i) Paper chromatography relies on partition between the solvent applied and another
phase.
What is this second phase? .......................................................
© UCLES 2007 9701/04/M/J/07
15 For
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(ii) The table below shows the Rf values for some amino acids in two different
solvents.
amino acid Rf solvent 1 Rf solvent 2
A 0.1 0.2
B 0.0 0.4
C 0.3 0.0
D 0.8 0.9
E 0.6 0.5
Use the grid below to plot the positions of the amino acids after two-dimensional
paper chromatography using solvent 1 followed by solvent 2.
solvent
front
solvent 1
spot applied
here solvent 2
solvent
front
(iii) Which amino acid travelled fastest in both solvents? .................................
(iv) Which amino acid did not move at all in solvent 2? .................................
[5]
[Total: 10]
16 For
Examiner’s
Use
9 (a) Graphite and buckminsterfullerene are two structural forms of carbon. By referring to
diagrams of their structures, suggest three differences in their properties.
graphite buckminsterfullerene
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(b) Nano-sized ‘test-tubes’ can be formed from carbon structures.

What is the relationship between the parts of these ‘test tubes’ and the two structural
forms of carbon shown above?
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(c) Many modern sunscreens contain nano-sized particles of titanium dioxide. This
substance does not absorb ultraviolet radiation.
Suggest how these nano-particles are able to protect skin from ultraviolet radiation.
..........................................................................................................................................
......................................................................................................................................[1]
[Total: 7]
University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of
Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.
© UCLES 2007 9701/04/M/J/07
*7262307684*
CHEMISTRY 9701/04
1 hour 45 minutes
Do not use staples, paper clips, highlighters, glue or correction fluid. For Examiner’s Use
1
Section A
2
Section B
Answer all questions. 3
You may lose marks if you do not show your working or if you do not use
4
appropriate units.
5
The number of marks is given in brackets [ ] at the end of each question or 6
part question.
7
10
Total
SPA (SHW (00018 4/07) T51891/2

2 For
Examiner’s
Use
Section A
1 Chlorine gas and iron(II) ions react together in aqueous solution as follows.
Cl 2 + 2Fe2+ 2Cl – + 2Fe3+
(a) The following diagram shows the apparatus needed to measure the E ocell for the above
reaction.
S
V
E
C
D
B
(i) In the spaces below, identify what the five letters A – E in the above diagram
represent.
A .........................................................
B .........................................................
C .........................................................
D .........................................................
E .........................................................
(ii) Use the Data Booklet to calculate the E ocell for this reaction, and hence decide which
direction (left to right, or right to left) electrons would flow through the voltmeter V
when switch S is closed.
E ocell = .................................................. V
direction of electron flow ......................................................

[7]
© UCLES 2008 9701/04/M/J/08
3 For
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Use
(b) Iron(III) chloride readily dissolves in water.
FeCl 3(s) Fe3+(aq) + 3Cl –(aq)
(i) Use the following data to calculate the standard enthalpy change for this process.
species DH of / kJ mol–1
FeCl 3(s) –399.5
Fe3+(aq) –48.5
Cl –(aq) –167.2
DH o = .........................................kJ mol–1
(ii) A solution of iron(III) chloride is used to dissolve unwanted copper from printed
circuit boards.
When a copper-coated printed circuit board is immersed in FeCl 3(aq), the solution
turns pale blue.
Suggest an equation for the reaction between copper and iron(III) chloride and use
the Data Booklet to calculate the E o for the reaction.
equation ...................................................................................................................
E o = .................................................. V
[4]
[Total: 11]
4 For
Examiner’s
Use
2 This question is about the properties and reactions of the oxides of some elements in their
+4 oxidation state.
(a) Chlorine dioxide, Cl O2, is an important industrial chemical, used to bleach wood pulp
for making paper, and to kill bacteria in water supplies.
However, it is unstable and decomposes into its elements as follows.
2Cl O2(g) Cl 2(g) + 2O2(g)
(i) The chlorine atom is in the middle of the Cl O2 molecule. Using the chlorine-oxygen
bond energy as 278 kJ mol–1, and other values from the Data Booklet, calculate DH
for the above reaction.
DH = ........................................ kJ mol–1
(ii) Assuming the Cl -O bonds in chlorine dioxide are double bonds, predict the shape
of the Cl O2 molecule. Explain your answer.
..................................................................................................................................
..................................................................................................................................
(iii) Cl O2 can be made in the laboratory by reacting KCl O3 with concentrated H2SO4.
Other products are K2SO4, KCl O4 and H2O.
Construct a balanced equation for this reaction. You may find the use of oxidation
numbers helpful.
..................................................................................................................................
[5]
(b) Sulphur dioxide is an atmospheric pollutant.
(i) State two sources of atmospheric SO2 that arise from human activity.
..................................................................................................................................
..................................................................................................................................
(ii) Explain why SO2 is a pollutant, and state an environmental consequence of this
pollution.
..................................................................................................................................
..................................................................................................................................
[3]
© UCLES 2008 9701/04/M/J/08
5 For
Examiner’s
Use
(c) All the oxides of the elements in Group IV in their +4 oxidation state are high melting
point solids except CO2.
(i) Explain this observation by describing the bonding in CO2, SiO2 and SnO2.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) State the difference in the thermal stabilities of SnO2 and PbO2. Illustrate your
answer with an equation.
..................................................................................................................................
..................................................................................................................................
CO2 dissolves in water to form a weakly acidic solution containing the hydrogencarbonate
ion.
(iii) Write an equation for the reaction of CO2 with water, and write an expression for
the equilibrium constant, Kc.
..................................................................................................................................
..................................................................................................................................
(iv) Explain the role of the hydrogencarbonate ion in controlling the pH of blood,
illustrating your answer with relevant equations.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[7]
[Total: 15]
6 For
Examiner’s
Use
3 The elements of Group IV all form tetrachlorides with the general formula M Cl 4.
(a) Draw a diagram of a molecule of SiCl 4 stating bond angles.
[2]
(b) Describe and explain how the volatilities of the Group IV chlorides vary down the group.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
(c) The relative stabilities of the M 2+(aq) and M 4+(aq) ions also vary down Group IV.
(i) Use the Data Booklet to illustrate this observation when M = Sn and M = Pb.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Use the Data Booklet to predict the products formed, and write equations for the
reactions occurring, when
• an equimolar mixture of Sn2+(aq) and Sn4+(aq) is added to I2(aq),
..................................................................................................................................
..................................................................................................................................
• an equimolar mixture of Pb2+(aq) and Pb4+(aq) is added to SO2(aq).
..................................................................................................................................
..................................................................................................................................
[4]
© UCLES 2008 9701/04/M/J/08
7 For
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Use
(d) (i) The Sn–Cl bond energy is +315 kJ mol–1. Use this and other values from the Data
Booklet to calculate DH o for the reaction
M Cl 2(g) + Cl 2(g) M Cl 4(g)
for the following cases.
• M = Si
DH o = ........................................ kJ mol–1
• M = Sn
DH o = ........................................ kJ mol–1
(ii) Do your results agree with the trend in relative stabilities of the +2 and +4 oxidation
states in (c)? Explain your answer.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 11]
8 For
Examiner’s
Use
4 Recently much interest has been shown in the production of the fuel biodiesel from algae.
Up to 55% of the mass of the dried algae is composed of lipids, the majority of which are
triglycerides.
To convert triglycerides into biodiesel, the following processes are carried out.
C17H35CO2CH2 CH2OH
I
C17H35CO2CH CHOH + 3C17H35CO2H
C17H35CO2CH2 CH2OH
a triglyceride, Mr = 890 glycerol
II
C17H35CO2H C17H35CO2CH3
biodiesel, Mr = 298
(a) Name the functional group present in triglycerides.
.................................................................................................................................... [1]
(b) Suggest reactants and conditions for
reaction I,
..........................................................................................................................................
reaction II.
..........................................................................................................................................
[4]
(c) Suggest the structural formula of the compound formed when glycerol is reacted with
(i) an excess of HBr(aq),
..................................................................................................................................
(ii) an excess of hot acidified K2Cr2O7(aq).
..................................................................................................................................
[2]
© UCLES 2008 9701/04/M/J/08
9 For
Examiner’s
Use
(d) Calculate the mass of biodiesel that can be produced from 1000 kg of dried algae,
assuming that 50% of the algal mass is triglycerides.
mass = ........................................... kg [2]
(e) (i) Construct an equation for the complete combustion of biodiesel.
..................................................................................................................................
(ii) Use your equation to calculate the mass of CO2 produced when 10 kg of biodiesel
is burned.
..................................................................................................................................
..................................................................................................................................
[3]
(f) The production of biodiesel is at present an expensive process.
Suggest a reason why the development of biodiesel as an alternative to fossil fuels is

important.
..........................................................................................................................................
.................................................................................................................................... [1]
[Total: 13]
10 For
Examiner’s
Use
5 Both ethene and benzene react with bromine, but the mechanisms and the types of products
of the two reactions are different.
reaction I
H2C CH2 + Br2 BrCH2CH2Br
no heat, no light, no catalyst needed
Br
reaction II
+ Br2 + HBr
heat and catalyst needed
(a) State the type of reaction undergone in each of reactions I and II.
reaction I
..........................................................................................................................................
reaction II
..........................................................................................................................................
[2]
© UCLES 2008 9701/04/M/J/08
11 For
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(b) In each of reactions I and II, the intermediate is a bromine-containing cation. In each
of the following boxes, draw the intermediate and use curly arrows to show how it is
converted into the product.
reaction I
product
intermediate
reaction II
product
intermediate
[4]
(c) Why do ethene and benzene differ in their reaction with bromine?
..........................................................................................................................................
.................................................................................................................................... [1]
[Total: 7]
12 For
Examiner’s
Use
Y
6 The substituted benzene compound can be further substituted.
If Y is an electron-withdrawing group, the next substitution will be in position 3.

If Y is an electron-releasing group, the next substitution will be mostly in position 4.
Y Y Y
if Y is electron-withdrawing if Y is electron-releasing
X +X +X
The following table lists some electron-withdrawing and electron-releasing substituents.
electron-withdrawing groups electron-releasing groups
–NO2 –CH3
–COCH3 –CH2Br
–CO2H –NH2
Use the above information to draw relevant structural formulae in the boxes in the schemes
below.
CH3
(i) KMnO4 + OH–
Br2 + Al Cl 3 (ii) H+
(i) KMnO4 + OH–

(ii) H+ A B
(i) Sn + HCl
HNO3 + H2SO4 (ii) OH–
C D E
[5]
[Total: 5]
© UCLES 2008 9701/04/M/J/08
13 For
Examiner’s
Use
7 Each of the following structures is an 8-atom segment of the chain of a commercial polymer.
For each structure,
• decide whether it is part of a condensation or an addition polymer, and

• draw the structural formulae of the monomer(s) from which the polymer is made.
addition or
polymer formulae of monomers
condensation?
O O
H
C CH2 N C
N CH2 C N
H H
O O
C CH2 C CH2
CH O CH O
CH2 CH3
CH3
CH3 CONH2 CONH2
CH CH CH CH
CH2 CH2 CH2 CH2
[8]
[Total: 8]
14 For
Examiner’s
Use
8 (a) State and show, using suitable diagrams, the types of bonding that occur in the primary,
secondary and tertiary structures of a protein.
primary
secondary
tertiary
[6]
(b) Analysis of a polypeptide A showed that the amino-(N-)terminal end is methionine (met)
and that the carboxyl-(C-)terminal end is lysine (lys).
Enzymic hydrolysis of the polypeptide produced the following tripeptides, with the amino
acid residue on the left having the free amino group.
met-ala-gly gly-arg-val ala-gly-arg arg-val-lys ala-gly-ala gly-ala-gly
Work out the sequence of amino acids in A, using the 3-letter abbreviations. Use each
tripeptide once only.
[2]
© UCLES 2008 9701/04/M/J/08
15 For
Examiner’s
Use
(c) Give two examples of how interchanging the positions of two amino acids could affect
the bonding in, and hence the overall structure of, the protein.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [4]
[Total: 12]
16 For
Examiner’s
Use
9 Much of the preparation of evidence to solve crimes now relies on instrumental analysis. This
question deals with some of the techniques used.
(a) Electrophoresis can be used to separate amino acids produced by hydrolysing proteins.
The amino acids are placed in a buffered solution in an electric field. In a solution of
given pH, what two factors affect the movement of a given amino acid?
(i) ..................................................................................................................................
(ii) ..................................................................................................................................
[2]
(b) Nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry are also used
in the detection of certain molecules, particularly those containing hydrogen atoms.
(i) Explain how and why the NMR spectrum of propanal, CH3CH2CHO, would be
different from that of propanone, CH3COCH3, which contains the same atoms.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Explain how and why the mass spectrum of the two compounds in (i) would be
different.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
© UCLES 2008 9701/04/M/J/08
17 For
Examiner’s
Use
(c) At one time, bromomethane, CH3Br, was widely used to control insect pests in agricultural
crops and timber. It is now known to break down in the stratosphere and contribute to
the destruction of the ozone layer.
Samples can be screened for traces of bromomethane by subjecting them to mass

spectrometry.
(i) Which peak(s) would show the presence of bromine in the compound?
..................................................................................................................................
(ii) How could you tell by studying the M and M+2 peaks that the compound contained
bromine rather than chlorine?
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 9]
18 For
Examiner’s
Use
10 (a) A number of drugs, such as insulin for diabetics, are delivered by injection rather than
by mouth (oral delivery). Suggest two reasons why this might be necessary.
(i) ..................................................................................................................................
..................................................................................................................................
(ii) ..................................................................................................................................
..................................................................................................................................
[2]
(b) Many patients prefer oral delivery to injection, and a number of methods for
overcoming the problems of oral delivery are being investigated. Several of these use
nanotechnology.
Study the passage and diagram and then answer the questions that follow.
At a 2004 meeting, engineers from the University of Texas described their research into
nanospheres for oral drug delivery. Nanospheres can transport a drug safely through
the hostile environment of the stomach.
The nanospheres are created from hydrogels which are stable, organic materials formed
from a network of polymer chains. Hydrogels have a variety of uses including disposable
nappies, soft contact lenses, dressings for burns and, more recently, drug delivery.
The drug is contained in the hydrogel nanosphere as shown in the diagram below.
Hydrogels absorb water and swell at a rate dependent on the pH of their environment.
As the hydrogel swells, the drug is released.
hydrogel
coat
capsule drug
containing nanospheres nanosphere
(i) What is a nanosphere?
..................................................................................................................................
(ii) Suggest why the stomach might be a particularly hostile environment for drugs.
..................................................................................................................................
..................................................................................................................................
© UCLES 2008 9701/04/M/J/08
19 For
Examiner’s
Use
(iii) Suggest two ways in which the nanosphere shown in the diagram can be modified
to change the rate of drug release.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
(c) Hydrogels may be formed as homopolymers (using a single monomer), or heteropolymers

(using two or more different monomers).
By using the monomers below, you are to draw sections of both a homopolymer and
a heteropolymer. Each of your drawings should show a three-monomer section of the
polymer.
HOCH2CH2OH HO2CCHRNH2 HO2CCH(OH)CH2CO2H
homopolymer
heteropolymer
[3]
[Total: 9]
© UCLES 2008 9701/04/M/J/08
20
BLANK PAGE
9701/04/M/J/08
*0737714930*
CHEMISTRY 9701/04
1 hour 45 minutes
Section A For Examiner’s Use

1
Section B
appropriate units. 3
4
The number of marks is given in brackets [ ] at the end of each question or part
question. 5
Total
This document consists of 18 printed pages and 2 blank pages.
SP (FF/DT) T69679/1
2
Section A For
Examiner’s
Answer all questions in the spaces provided. Use
1 (a) Explain what is meant by the Bronsted-Lowry theory of acids and bases.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(b) The Ka values for some organic acids are listed below.
acid Ka /mol dm−3
CH3CO2H 1.7 10−5
Cl CH2CO2H 1.3 10−3
Cl 2CHCO2H 5.0 10−2
(i) Explain the trend in Ka values in terms of the structures of these acids.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Calculate the pH of a 0.10 mol dm−3 solution of Cl CH2CO2H.
pH = ...........................................
© UCLES 2009 9701/04/M/J/09
3
(iii) Use the following axes to sketch the titration curve you would obtain when 20 cm3 of For
0.10 mol dm−3 NaOH is added gradually to 10 cm3 of 0.10 mol dm−3 Cl CH2CO2H. Examiner’s
Use
14
pH 7
0
0 5 10 15 20
volume of NaOH added / cm3
[8]
(c) (i) Write suitable equations to show how a mixture of ethanoic acid, CH3CO2H, and
sodium ethanoate acts as a buffer solution to control the pH when either an acid or
an alkali is added.
..................................................................................................................................
..................................................................................................................................
(ii) Calculate the pH of a buffer solution containing 0.10 mol dm−3 ethanoic acid and
0.20 mol dm−3 sodium ethanoate.
pH = ...........................................
[4]
[Total: 14]
4
2 (a) Describe the observations you would make when concentrated sulfuric acid is added For
to separate portions of NaCl (s) and NaBr(s). Write an equation for each reaction that Examiner’s
occurs. Use
NaCl (s): observation ................................................................................................
......................................................................................................................
equation
NaBr(s): observation ................................................................................................
......................................................................................................................
equation
[4]
(b) By quoting relevant E o- data from the Data Booklet, explain how the observations you
have described above relate to the relative oxidising power of the elements.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(c) By referring to relevant E o- data choose a suitable reagent to convert Br2 into Br −. Write
an equation and calculate the E o- for the reaction.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
[Total: 9]
© UCLES 2009 9701/04/M/J/09
5
3 (a) Explain what is meant by the term transition element. For

Examiner’s
.......................................................................................................................................... Use
..................................................................................................................................... [1]
(b) Complete the electronic configuration of
(i) the vanadium atom, 1s22s22p6 .......................................................................
(ii) the Cu2+ ion. 1s22s22p6 .......................................................................

[2]
(c) List the four most likely oxidation states of vanadium.
..................................................................................................................................... [1]
(d) Describe what you would see, and explain what happens, when dilute aqueous ammonia
is added to a solution containing Cu2+ ions, until the ammonia is in an excess.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [5]
(e) Copper powder dissolves in an acidified solution of sodium vanadate(V), NaVO3, to

produce a blue solution containing VO2+ and Cu2+ ions.
By using suitable half-equations from the Data Booklet, construct a balanced equation
for this reaction.
..................................................................................................................................... [2]
[Total: 11]
6
4 (a) The reaction between iodide ions and persulfate ions, S2O 82−, is slow. For
Examiner’s
2I− + S2O 82− I2 + 2SO 42− 1 Use
The reaction can be speeded up by adding a small amount of Fe2+ or Fe3+ ions. The
following two reactions then take place.
2I− + 2Fe3+ I2 + 2Fe2+ 2
2Fe2+ + S2O 82− 2Fe3+ + 2SO 42− 3
(i) What type of catalysis is occurring here?
..................................................................................................................................
(ii) The rates of reactions 2 and 3 are both faster than that of reaction 1. By considering
the species involved in these reactions, suggest a reason for this.
..................................................................................................................................
..................................................................................................................................
(iii) The following reaction pathway diagram shows the enthalpy profile of reaction 1.
enthalpy
progress of reaction
Use the same axes to draw the enthalpy profiles of reaction 2 followed by reaction
3, starting reaction 2 at the same enthalpy level as reaction 1.
[4]
© UCLES 2009 9701/04/M/J/09
7
(b) The oxidation of SO2 to SO3 in the atmosphere is speeded up by the presence of For
nitrogen oxides. Examiner’s
Use
(i) Describe the environmental significance of this reaction.
..................................................................................................................................
(ii) Describe a major source of SO2 in the atmosphere.
..................................................................................................................................
(iii) By means of suitable equations, show how nitrogen oxides speed up this reaction.
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 8]
8
5 (a) In the following boxes draw the structural formulae of three alcohols having straight For
(i.e. unbranched) chains, with the molecular formula C5H12O. Examiner’s
Use
A B C
[2]
Use the letters A, B or C as appropriate when answering the following questions. Each
letter may be used once, more than once or not at all.
(b) Which of the alcohols are chiral? .................................................................................. [1]
(c) (i) Which of these alcohols react with alkaline aqueous iodine? ...................................
(ii) Describe the observation you would make during this reaction.
..................................................................................................................................
(iii) Draw the structural formulae of the products of this reaction.
[4]
(d) Draw the structural formula of the product obtained when each of the alcohols A, B and
C is heated with an excess of acidified K2Cr2O7(aq).
[3]
© UCLES 2009 9701/04/M/J/09
9
(e) One of the many suggestions for converting biomass into liquid fuel for motor transport For
is the pyrolysis (i.e. heating in the absence of air) of cellulose waste, followed by the Examiner’s
synthesis of alkanes. Use
(i) In the first reaction, cellulose, (C6H10O5)n, is converted into a mixture of carbon
monoxide and hydrogen. Some carbon is also produced.
Complete and balance the equation for this reaction.
(C6H10O5)n ————————— + ————————— + —————————

(ii) The second reaction involves the combination of CO and H2 to produce alkanes
such as heptane.
7CO + 15H2 C7H16 + 7H2O

heptane
Using the value of 1080 kJ mol−1 as the value for the C⬅O bond energy in CO,
and other relevant bond energies from the Data Booklet, calculate the ∆H for this
reaction.
∆H = ......................................... kJ mol−1
[5]
[Total: 15]
10
6 Phenol and chlorobenzene are less reactive towards certain reagents than similar non-aromatic For
compounds. Examiner’s
Thus hexan-1-ol can be converted into hexylamine by the following two reactions, Use
I II
CH3(CH2)5OH CH3(CH2)5Cl CH3(CH2)5NH2
hexan-1-ol 1-chlorohexane hexylamine
whereas neither of the following two reactions takes place.
OH Cl NH2
(a) (i) Suggest reagents and conditions for
reaction I, ............................................................................................................... ,
reaction II. ............................................................................................................... .
(ii) What type of reaction is reaction II? ..........................................................................
(iii) Suggest a reason why chlorobenzene is much less reactive than 1-chlorohexane.
..................................................................................................................................
..................................................................................................................................
[4]
© UCLES 2009 9701/04/M/J/09
11
(b) Phenylamine can be made from benzene by the following two reactions. For
Examiner’s
Use
III NO2 IV NH2
(i) Suggest reagents and conditions for
reaction III, .............................................................................................................. ,
reaction IV. .............................................................................................................. .
(ii) State the type of reaction for
reaction III, .............................................................................................................. ,
reaction IV. .............................................................................................................. .

[5]
(c) Suggest a reagent that could be used to distinguish phenylamine from hexylamine.
reagent and conditions ....................................................................................................
observation with phenylamine ..........................................................................................
observation with hexylamine.............................................................................................

[2]
12
(d) Phenylamine is used to make azo dyes. In the following boxes draw the structural formula For
of the intermediate D and of the azo dye E. Examiner’s
Use
NH2
NaNO2 + HCl
CH3
T < 5°C
OH
CH3
D
in NaOH(aq)
E
[2]
[Total: 13]
© UCLES 2009 9701/04/M/J/09
13
Section B For
Examiner’s
7 Metals play a vital part in biochemical systems. In this question you need to consider why
some metals are essential to life, whilst others are toxic.
(a) For each of the metals, state where it might be found in a living organism, and what its
chemical role is.
iron location in organism .....................................................................................
role ...............................................................................................................
......................................................................................................................
sodium location in organism .....................................................................................
role ...............................................................................................................
......................................................................................................................
zinc location in organism .....................................................................................
role ...............................................................................................................
......................................................................................................................
[6]
(b) Heavy metals such as mercury are toxic, and it is important that these do not enter the
food chain.
(i) Give a possible source of mercury in the environment.
..................................................................................................................................
(ii) Describe and explain two reasons why mercury is toxic, using diagrams and/or equations
to help your explanation.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total : 10]
14
8 A large number of organic compounds are soluble in both water and non-aqueous solvents For
such as hexane. If such a compound is shaken with a mixture of water and the non-aqueous Examiner’s
solvent, it will dissolve in both solvents depending on the solubility in each. Use
(a) (i) State what is meant by the term partition coefficient.
..................................................................................................................................
..................................................................................................................................
(ii) When 100 cm3 of an aqueous solution containing 0.50 g of an organic compound X
was shaken with 20 cm3 of hexane, it was found that 0.40 g of X was extracted into
the hexane.
Calculate the partition coefficient of X between hexane and water.
(iii) If two 10 cm3 portions of hexane were used instead of a single 20 cm3 portion,
calculate the total amount of X extracted and compare this with the amount
extracted using one 20 cm3 portion.
[5]
© UCLES 2009 9701/04/M/J/09
15
(b) PCBs are highly toxic compounds released into the atmosphere when some plastics For
are burned at insufficiently high temperatures. In recent years PCB residues have been Examiner’s
found in the breast milk of Inuit mothers in northern Canada. Foods, such as oily fish, Use
seal and whale meat, which are high in fat, form an important part of the Inuit diet.
(i) Suggest why berries and drinking water are not contaminated by PCBs in the same
way that oily fish, seal and whale meat are.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Based on the information provided, what can you say about the partition coefficient
between fat and water for PCB residues?
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[3]
16
(c) The diagram shows the result of two-way paper chromatography. For
Examiner’s
Use
solvent
2
X
starting point
solvent 1
(i) How many spots were there after the first solvent had been used?
...................................
(ii) Circle the spot that moved very little in solvent 2, but moved a greater distance in
solvent 1.
(iii) Draw a square around the spot that could be separated from the rest by using only
solvent 1.
[3]
[Total: 11]
© UCLES 2009 9701/04/M/J/09
17
9 (a) Spider silk is a natural polymer which has an exceptional strength for its weight. Kevlar For
is a man-made polymer designed to have similar properties. It has a wide variety of Examiner’s
uses from sporting equipment to bullet-proof vests. Use
H
N
O C
C O
H N
N H
O C
C O
N
H
C
O
Kevlar
(i) In Kevlar, the polymer strands line up to form strong sheets with bonds between
the strands.
On the diagram above, draw part of a second polymer chain showing how bonds
could be formed between the chains.
(ii) Suggest what type of bonds these are.
..................................................................................................................................
(iii) Draw two possible monomer molecules for making the polymer Kevlar.
[5]
© UCLES 2009 9701/04/M/J/09
18
(b) The transport of oil by sea has resulted in a number of oil spills in recent years. As well
as a waste of a valuable resource, these have caused major environmental problems.
Traditional sorbent materials absorb water and sink. Researchers have developed new
sorbent materials to help collect the spilled oil. The sorbent consists of a material called
‘hydrophobic aerogels’. This is a network of silicon(IV) oxide with some of the silicon
atoms attached to fluorine-containing groups.
—O—Si—CH2—CF3
The introduction of these fluorine-containing groups allows the oil to be absorbed but not
the water. Tests show that these materials can absorb more than 200 times their mass of oil
without sinking.
(i) Suggest what the word hydrophobic means.
..................................................................................................................................
(ii) Suggest why the fluorine-containing groups allow oil to pass through but not water
molecules.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) Suggest another important fluorine-containing polymer that repels water-containing

materials.
..................................................................................................................................
[4]
[Total: 9]
© UCLES 2009 9701/04/M/J/09
19
BLANK PAGE
9701/04/M/J/09
20
BLANK PAGE
Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable
effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will
be pleased to make amends at the earliest possible opportunity.
9701/04/M/J/09
*8342870404*
CHEMISTRY 9701/41
1 hour 45 minutes
Do not use staples, paper clips, highlighters, glue or correction fluid. For Examiner’s Use
1
Section A
2
Section B
5
question. 6
10
Total
DC (CW/DJ) 25442/4
www.XtremePapers.net
2
Section A For
Examiner’s
1 (a) Phosphorus and sulfur are two non-metallic elements on the right hand side of the
Periodic Table.
For each of these elements describe the observations you would make when it burns in
air, and write a balanced equation for the reaction.
phosphorus
observation ......................................................................................................................
equation ...........................................................................................................................
sulfur
observation ......................................................................................................................
equation ...........................................................................................................................
[4]
(b) White phosphorus, P4, is produced commercially by heating calcium phosphate(V) rock
with a mixture of silica, SiO2, and coke in an electric furnace at 1400 °C. Calcium silicate,
CaSiO3, and carbon monoxide are the other products.
(i) Balance the following equation which represents the overall process.
___ Ca3(PO4)2 + ___ SiO2 + ___ C ___ P4 + ___ CaSiO3 + ___ CO
When heated to 400 °C in the absence of air, white phosphorus is changed into the red
form of the element. The following table lists some of the properties of the two forms,
which are known as allotropes.
electrical melting point solubility in solubility in

allotrope
conductivity / °C water benzene
white none 44 insoluble soluble
red none 500 insoluble insoluble
(ii) Suggest the type of structure and bonding in each allotrope.
allotrope type of structure type of bonding

white
red
© UCLES 2010 9701/41/M/J/10
3
(iii) In both allotropes, phosphorus has a valency of 3. Suggest by means of diagrams For
how the phosphorus atoms might be joined together in each allotrope. Examiner’s
Use
white phosphorus red phosphorus

[7]
[Total: 11]
4
2 (a) Describe three characteristic chemical properties of transition elements that are not For
shown by Group II elements. Examiner’s
Use
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
(b) When NH3(aq) is added to a green solution containing Ni2+(aq) ions, a grey-green
precipitate is formed. This precipitate dissolves in an excess of NH3(aq) to give a blue-
violet solution.
Suggest an explanation for these observations, showing your reasoning and including
equations for the reactions you describe.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [4]
(c) Dimethylglyoxime, DMG, is a useful reagent for the quantitative estimation of nickel. It
forms an insoluble salt with nickel ions according to the following equation.
Ni2+(aq) + C4H8N2O2 NiC4H6N2O2(s) + 2H+(aq)

DMG Ni-DMG
A small coin of mass 3.40 g was dissolved in nitric acid and an excess of DMG was
added. The precipitated Ni-DMG was filtered off, washed and dried. Its mass was
4.00 g.
Calculate the % of nickel in the coin.
percentage of nickel = ..................................% [3]
[Total: 10]
© UCLES 2010 9701/41/M/J/10
5
3 (a) Describe how the behaviour of the oxides of tin and lead in their +4 oxidation states For
differ on heating. Examiner’s
Use
..........................................................................................................................................
...................................................................................................................................... [1]
(b) Explain the following by using data from the Data Booklet where appropriate, and writing
equations for all reactions.
(i) A sample of liquid PbCl4 is placed in a flask and the flask is gently warmed. A gas
is evolved and a white solid is produced. When the gas is bubbled through KI(aq),
purple fumes are produced.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Repeating the same experiment using liquid SnCl4 instead of PbCl4 results in no
evolution of gas, and no reaction with KI(aq).
..................................................................................................................................
..................................................................................................................................
[4]
(c) The molecule dichlorocarbene, CCl2, can be produced under certain conditions. It is
highly unstable, reacting with water to produce carbon monoxide and a strongly acidic
solution.
(i) Suggest the electron arrangement in CCl2 and draw a dot-and-cross diagram
showing this. Predict the shape of the molecule.
(ii) Construct an equation for the reaction of CCl2 with water.
..................................................................................................................................
[3]
[Total: 8]
6
4 Ethanolamine and phenylamine are two organic bases that are industrially important. For
Ethanolamine is a useful solvent with basic properties, whilst phenylamine is an important Examiner’s
starting material in the manufacture of dyes and pharmaceuticals. Use
The following table lists some of their properties, together with those of propylamine.
compound formula Mr boiling point/ °C solubility in

water
propylamine CH3CH2CH2NH2 59 48 fairly soluble
ethanolamine HOCH2CH2NH2 61 170 very soluble
sparingly
phenylamine NH2 93 184
soluble
(a) Suggest why the boiling point of ethanolamine is much higher than that of propylamine.
Draw a diagram to illustrate your answer.
..........................................................................................................................................
..........................................................................................................................................
[2]
(b) Describe and explain the relative basicities of propylamine and phenylamine.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(c) Write an equation showing ethanolamine acting as a Brønsted-Lowry base.
...................................................................................................................................... [1]
© UCLES 2010 9701/41/M/J/10
7
(d) Propylamine can be synthesised from bromoethane by the following route. For
Examiner’s
Use
step 1 step 2
CH3CH2Br CH3CH2CH2NH2
(i) Draw the structure of the intermediate compound X in the box above.
(ii) Suggest reagents and conditions for
step 1 ........................................................................................................................
step 2 ........................................................................................................................
[3]
(e) Apart from their relative basicities, ethanolamine and phenylamine differ in many of their
reactions.
For each of these two compounds, describe one test that would give a positive result
with the stated compound, but a negative result with the other.
ethanolamine
test ...................................................................................................................................
observation ......................................................................................................................
phenylamine
test ...................................................................................................................................
observation ......................................................................................................................
[4]
[Total: 12]
8
5 Although standard electrode potentials are measured for solutions where the concentrations For
of ions are 1.0 mol dm–3, cells used as sources of battery power tend to operate with more Examiner’s
concentrated solutions. This question concerns the electrode reactions involved in the Use
hydrogen-oxygen fuel cell and the lead-acid car battery.
(a) In the hydrogen-oxygen fuel cell, H2(g) and O2(g) are fed onto two inert electrodes
dipping into NaOH(aq).
oxygen
hydrogen
NaOH(aq)
The following reactions take place.
left hand electrode (cathode): H2(g) + 2OH–(aq) 2H2O(l) + 2e–
right hand electrode (anode): O2(g) + 2H2O(l) + 4e– 4OH–(aq)
(i) Use the Data Booklet to calculate E –cell

o–
for this reaction.
..................................................................................................................................
(ii) Construct an equation for the overall reaction.
..................................................................................................................................
(iii) By using one of the phrases more positive, more negative or no change, deduce
the effect of increasing [OH–(aq)] on the electrode potential of
• the left hand electrode .......................................................................
• the right hand electrode .......................................................................
(iv) Hence deduce whether the overall Ecell is likely to increase, decrease or remain the
same, when [OH–(aq)] increases. Explain your answer.
..................................................................................................................................
..................................................................................................................................
(v) Suggest one other reason why a high [NaOH(aq)] is used in the fuel cell.
..................................................................................................................................
[6]
© UCLES 2010 9701/41/M/J/10
9
(b) In the cells of a lead-acid car battery the following reactions take place. For
Examiner’s
cathode: Pb(s) Pb2+(aq) + 2e– Use
anode: PbO2(s) + 4H+(aq) + 2e– Pb2+(aq) + 2H2O(l)
(i) Use the Data Booklet to calculate E –cell

o–
for this reaction.
..................................................................................................................................
(ii) Construct an equation for the overall reaction.
..................................................................................................................................
The electrolyte in a lead-acid cell is H2SO4(aq). Most of the Pb2+(aq) ions that are
produced at the electrodes are precipitated as the highly insoluble PbSO4(s).
(iii) Construct an equation for the overall cell reaction in the presence of H2SO4.
..................................................................................................................................
(iv) By considering the effect of decreasing [Pb2+(aq)] on the electrode potentials of

the cathode and the anode, deduce the effect of the presence of H2SO4(aq) in the
electrolyte on the overall Ecell.
State hether
w E cell will increase, decrease or remain the same.
the
Overall Ecell will ................................................ .
Explain oury wer.

ans
..................................................................................................................................
..................................................................................................................................
[5]
[Total: 11]
10
6 Acyl chlorides are useful intermediates in organic syntheses. For

Examiner’s
(a) (i) State a suitable reagent for converting carboxylic acids into acyl chlorides. Use
..................................................................................................................................
(ii) Construct an equation for the reaction between ethanoic acid, CH3CO2H, and the
reagent you have stated in (i).
..................................................................................................................................
[2]
(b) (i) In the boxes provided draw the structures of the compounds formed when benzoyl
chloride undergoes the following reactions.
COCl
C2H5OH NH3
I II
A B
(ii) Name the functional group in
• compound A ..................................................................
• compound B ................................................................. .
(iii) What type of reaction is reaction II?
..................................................................................................................................
[5]
© UCLES 2010 9701/41/M/J/10
11
(c) (i) Suggest suitable acyl chlorides to use in the following reaction. Draw their structures For
in the boxes provided. Examiner’s
Use
O O
+ H 2N HN NH
NH2
C E
OH
O
O
+
O O
O n
D OH F
Compound E dissolves in, but does not react with, cold water.
(ii) Suggest the major type of intermolecular interaction that occurs between E and
water.
..................................................................................................................................
(iii) A solution of the diamine H2NCH2CH2NH2 in water has pH = 11 but a solution of E

in water has pH = 7. Suggest why this is the case.
..................................................................................................................................
..................................................................................................................................
(iv) What type of polymer is compound F?
..................................................................................................................................
[5]
[Total: 12]
12
7 Predict the products of the following reactions and draw their structures in the boxes provided. For
Note that the molecular formula of the final product is given in each case. Examiner’s
Use
Cl2 + light NaOH
heat
C8H10O
Cl2 + AlCl3 HNO3 +
H2SO4
55˚C
C8H8ClO2N
KMnO4
+ OH– CH3OH +
+ heat conc. H2SO4
then H+ heat
C10H10O4
[6]
[Total: 6]
© UCLES 2010 9701/41/M/J/10
13
BLANK PAGE
14
Section B For
Examiner’s
8 The molecule that contains the genetic information for an individual organism is called
deoxyribonucleic acid, DNA.
(a) The diagram shows part of a DNA molecule. Study the diagram and identify the blocks
labelled J, K, L and M as accurately as you can.
J cytosine K
adenine M
block letter identity

J
K
L
M
[3]
(b) The DNA molecule is formed from two polymer strands.

What stops these strands from separating from each other?
..........................................................................................................................................
...................................................................................................................................... [2]
© UCLES 2010 9701/41/M/J/10
15
(c) List three differences between the structures of DNA and RNA. For
Examiner’s
1. ...................................................................................................................................... Use
..........................................................................................................................................
..........................................................................................................................................
2. ......................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
3. ......................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[3]
(d) Outline the different roles of mRNA and tRNA in the processes of transcription and
translation.
mRNA ..............................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
tRNA ................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[2]
[Total: 10]
16
9 A range of modern analytical techniques has made the identification of molecules, and atoms For
in compounds, much more rapid than traditional laboratory analysis. Examiner’s
Use
(a) One instrumental technique is NMR spectroscopy, which uses the fact that under certain
conditions protons can exist in two different energy states.
Explain how these different energy states arise.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) When methanol, CH3OH, is examined using NMR spectroscopy, it absorbs at two
different frequencies. Explain why, and predict the relative areas of the two peaks.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(c) The NMR spectrum below is that of one of three possible isomers of molecular formula
C3H6O2.
A B
1 09 8 7 6 5 4 3 2 1 0
chemical shift, δ / ppm
© UCLES 2010 9701/41/M/J/10
17
The compound could be propanoic acid, methyl ethanoate or ethyl methanoate. For
Examiner’s
(i) In the boxes provided, draw the structures of the three compounds. Use
propanoic acid methyl ethanoate ethyl methanoate
(ii) Explain which compound produced the spectrum shown, indicating which protons
are responsible for each of the peaks A and B.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) The NMR spectrum of another of the compounds has a peak at δ11.0.
State which compound this would be, and identify the proton(s) responsible for this
peak.
compound ..................................................
proton(s) ..................................................
[4]
(d) X-ray crystallography is a technique used to identify the relative positions of atoms in a
crystal of a compound.
(i) What further information about organic macromolecules can be deduced by the
use of X-ray crystallography?
..................................................................................................................................
..................................................................................................................................
(ii) Which atoms cannot be located by X-ray crystallography?
........................................................
[2]
[Total: 10]
18
10 The nature and variety of drugs that are available to treat diseases or life-threatening For
conditions has never been greater. At the same time, we are much better able to deliver Examiner’s
drugs to their targets in the body. Use
(a) Some drugs have to be given by injection, rather than by mouth.

Name a functional group in a drug molecule that might be broken down by the acid in
the stomach.
...................................................................................................................................... [1]
(b) The anti-cancer drug Taxol could be broken down if taken by mouth.
O
O NH O O
OH
O
H
OH
HO
OO O
O
O
Taxol
Circle two bonds, each in a different functional group, that could be hydrolysed in the
digestive system. [2]
© UCLES 2010 9701/41/M/J/10
19
(c) One way of protecting drug molecules that are taken by mouth is to enclose them in For
liposomes. These are artificially created spheres made from phospholipids which have Examiner’s
an ionic phosphate ‘head’ and two hydrocarbon ‘tails’. Use
A B C
phospholipid
(i) State in which area of the liposome, A, B or C, each of the following types of drug
would be carried.
a hydrophilic drug .........................
a hydrophobic drug .......................
(ii) For the remaining position, A, B or C, explain why this would not be a suitable area
for carrying a drug.
..................................................................................................................................
..................................................................................................................................
[3]
(d) One way of carrying drugs in the bloodstream is to attach them by a chemical bond to a
polymer. One such polymer is polyethylene glycol or PEG.
HO – (CH2 – CH2 – O)n – H
(i) Where would a drug be attached to a molecule of PEG?
..................................................................................................................................
(ii) Suggest why a liposome can carry more drug molecules than a molecule of PEG.
..................................................................................................................................
..................................................................................................................................
[2]
20
(e) Better-targeted delivery of drugs allows smaller amounts to be used, which brings For
significant advantages. Examiner’s
Suggest two advantages of using smaller drug doses. Use
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
[Total: 10]
© UCLES 2010 9701/41/M/J/10
*4308885825*
CHEMISTRY 9701/42
1 hour 45 minutes
Section A
Section B
3
question. 4
Total
DC (SM/CGW) 22690/3
2
Section A For
Examiner’s
1 Phenacyl chloride has been used as a component of some tear gases. Its lachrymatory and
irritant properties are due to it reacting with water inside body tissues to produce hydrochloric
acid.
It undergoes a nucleophilic substitution reaction with NaOH(aq).
Cl
+ OH– +
phenacyl chloride
(a) Write the formulae of the products of this reaction in the two boxes above. [2]
When the rate of this reaction was measured at various concentrations of the two reagents,
the following results were obtained.
experiment number [phenacyl chloride] [NaOH] relative rate
1 0.020 0.10 1.0
2 0.030 0.10 1.5
3 0.025 0.20 2.5
(b) (i) What is meant by the term order of reaction?
..................................................................................................................................
(ii) Use the above data to deduce the order with respect to each reactant. Explain your
reasoning.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) Write the overall rate equation for the reaction.
..................................................................................................................................
© UCLES 2010 9701/42/M/J/10
3
(iv) Describe the mechanism for this reaction that is consistent with your overall rate For
equation. Examiner’s
You should show all intermediates and/or transition states and partial charges, and Use
you should represent the movements of electron pairs by curly arrows.
[7]
(c) (i) Describe an experiment that would show that CH3COCl reacts with water at a
much faster rate than phenacyl chloride. Include the reagents you would use, and
the observations you would make with each chloride.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Suggest an explanation for this difference in reactivity.
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 13]
4
2 (a) Describe and explain how the solubilities of the sulfates of the Group II elements vary For
down the group. Examiner’s
Use
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
(b) The following table lists some enthalpy changes for magnesium and strontium
compounds.
enthalpy change value for magnesium value for strontium

/ kJ mol–1 / kJ mol–1
lattice enthalpy of M (OH)2 –2993 –2467
enthalpy change of hydration of M 2+(g) –1890 –1414
enthalpy change of hydration of OH–(g) –550 –550
o
(i) Use the above data to calculate values of ΔH solution for Mg(OH)2 and for Sr(OH)2.
Mg(OH)2 ...................................................................................................................
..................................................................................................................................
o
ΔH solution = ..................................... kJ mol–1
Sr(OH)2 ....................................................................................................................
..................................................................................................................................
o
ΔH solution = ..................................... kJ mol–1
(ii) Use your results in (i) to suggest whether Sr(OH)2 is more or less soluble in water
than is Mg(OH)2. State any assumptions you make.
..................................................................................................................................
..................................................................................................................................
(iii) Suggest whether Sr(OH)2 would be more or less soluble in hot water than in cold.
Explain your reasoning.
..................................................................................................................................
..................................................................................................................................
[5]
© UCLES 2010 9701/42/M/J/10
5
(c) Calcium hydroxide, Ca(OH)2, is slightly soluble in water. For

Examiner’s
(i) Write an expression for Ksp for calcium hydroxide, and state its units. Use
Ksp = units ............................................
(ii) 25.0 cm3 of a saturated solution of Ca(OH)2 required 21.0 cm3 of 0.0500 mol dm–3
HCl for complete neutralisation.
Calculate the [OH–(aq)] and the [Ca2+(aq)] in the saturated solution, and hence
calculate a value for Ksp.
[OH–(aq)] = .................................
[Ca2+(aq)] = ................................
Ksp = .........................................................................................
(iii) How would the solubility of Ca(OH)2 in 0.1 mol dm–3 NaOH compare with that in
water?
Explain your answer.
..................................................................................................................................
..................................................................................................................................
[6]
[Total: 14]
6
3 (a) Fluorine is much more electronegative than both silicon and sulfur, but whereas the For
molecule of SF4 has an overall dipole, that of SiF4 has none. Examiner’s
Use
Suggest a reason for this difference.
..........................................................................................................................................
...................................................................................................................................... [1]
(b) Predict whether or not the following molecules will have an overall dipole. Place a tick in
the appropriate column.
compound molecule has an molecule does not have

overall dipole an overall dipole
BCl 3
PCl 3
CCl 4
SF6
[2]
(c) Boron and silicon are two elements adjacent to carbon in the periodic table. CCl4 does
not react with water, whereas BCl 3 and SiCl4 do react.
(i) Suggest a reason for this difference in reactivity.
..................................................................................................................................
..................................................................................................................................
(ii) Construct equations showing the reaction of these two chlorides with an excess of
water.
BCl 3 .........................................................................................................................
SiCl4 .........................................................................................................................
[3]
© UCLES 2010 9701/42/M/J/10
7
(d) When reacted with a small quantity of water, SiCl 4 produces an oxychloride X, SixCl yOz. For
The mass spectrum of X shows peaks at mass numbers of 133, 149, 247, 263 and 396. Examiner’s
Use
(You should assume that the species responsible for all these peaks contain the 16O,
the 35Cl and the 28Si isotopes only.)
(i) Use these data to deduce the molecular formula of X.
molecular formula .........................................
(ii) Suggest the structures of the fragments responsible for the peaks at the following
mass numbers.
mass number structure
133
247
263
(iii) Hence suggest the displayed formula of X.
[5]
[Total: 11]
8
4 (a) Complete the electronic structures of the Cr3+ and Mn2+ ions. For
Examiner’s
Cr3+ 1s22s22p6 ............. Use
Mn2+ 1s22s22p6 .............

[2]
(b) (i) Describe what observations you would make when dilute KMnO4(aq) is added
slowly and with shaking to an acidified solution of FeSO4(aq) until the KMnO4 is in
a large excess.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Construct an ionic equation for the reaction that occurs.
..................................................................................................................................
[4]
(c) By selecting relevant E o data from the Data Booklet explain why acidified solutions of
Fe2+(aq) are relatively stable to oxidation by air, whereas a freshly prepared precipitate
of Fe(OH)2 is readily oxidised to Fe(OH)3 under alkaline conditions.
relevant E o values and half equations
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
explanation
..........................................................................................................................................
..........................................................................................................................................
[4]
© UCLES 2010 9701/42/M/J/10
9
(d) Predict the organic products of the following reactions and draw their structures in the For
boxes below. You may use structural or skeletal formulae as you wish. Examiner’s
Use
hot conc.
MnO4– + H+
hot conc.
MnO4– + H+
hot
OH Cr2O72– + H+
OH
[4]
(e) KMnO4 and K2Cr2O7 are the reagents that can be used to carry out the following
transformation.
CHO
I II
OH
(i) Draw the structure of intermediate E in the box above.
(ii) Suggest reagents and conditions for the following.
reaction I ...................................................................................................................
reaction II ..................................................................................................................
[3]
[Total: 17]
10
5 (a) (i) Briefly explain why the benzene molecule is planar. For
Examiner’s
.................................................................................................................................. Use
..................................................................................................................................
..................................................................................................................................
(ii) Briefly explain why all the carbon-carbon bonds in benzene are the same length.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[2]
(b) Benzene can be nitrated by warming it with a mixture of concentrated sulfuric and
nitric acids.
(i) By means of an equation, illustrate the initial role of the sulfuric acid in this
reaction.
..................................................................................................................................
(ii) Name the type of reaction and describe the mechanism for the nitration reaction,
including curly arrows showing the movement of electrons and all charges.
type of reaction .........................................................................................................
mechanism
[4]
(c) State the reagents and conditions needed to convert benzene into chlorobenzene.
...................................................................................................................................... [1]
© UCLES 2010 9701/42/M/J/10
11
(d) Nitrobenzene undergoes further substitution considerably more slowly than chlorobenzene. For
In nitrobenzene the incoming group joins to the benzene ring in the 3-position, whereas Examiner’s
in chlorobenzene the incoming group joins to the benzene ring in the 4-position. Use
(i) Use these ideas to suggest the structures of the intermediate compounds Y and Z
in the following synthesis of 4-chlorophenylamine.
NH2
I II III
Cl
Y Z
(ii) Suggest the reagents and conditions needed for reaction III in the above
synthesis.
..................................................................................................................................
..................................................................................................................................
(iii) Suggest the structural formulae of the products A, B, C and D of the following
reactions. If no reaction occurs write “no reaction” in the relevant box.
NH2
Br2(aq) CH3COCl
A Cl B
–
OH (aq) NaNO2
+ HCl
C D
[8]
[Total: 15]
12
Section B For
Examiner’s
6 Human hair and silk both consist of proteins. Proteins are described as having three major
levels of structure: primary, secondary and tertiary.
(a) Outline what is meant by the terms primary structure and tertiary structure of a protein.
primary structure ..............................................................................................................
..........................................................................................................................................
..........................................................................................................................................
tertiary structure ..............................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[2]
(b) In hair, the secondary structure consists of α-helices which are cross-linked by
disulfide bonds. The amino acid responsible for this cross-linking is cysteine,
H2NCH(CH2SH)CO2H.
(i) Show by means of a diagram how the disulfide cross-links are formed.
(ii) What type of reaction is this?
..................................................................................................................................
© UCLES 2010 9701/42/M/J/10
13
(iii) State three other interactions that stabilise the tertiary structure of proteins. For
Examiner’s
.................................................................................................................................. Use
..................................................................................................................................
..................................................................................................................................
[4]
(c) The β-pleated sheet is a different form of secondary structure found in proteins, such as
those in silk.
(i) What type of bonding is responsible for stabilising the β-pleated sheet in silk?
..................................................................................................................................
(ii) On the diagram below, draw a second polypeptide strand and show how bonds
would be formed that stabilise this β-pleated sheet.
R H O R H O
CH N C CH N C
N C CH N C CH
H O R H O R
[3]
(d) The cysteine-containing protein in hair is called α-keratin. A similar sequence of amino
acids can produce β-keratin proteins found in the scales, claws and shells of reptiles
such as tortoises. In β-keratin the secondary structure of the protein is in the form of a
β-pleated sheet.
Suggest what makes the β-pleated sheet in β-keratin so much less flexible than the
β-pleated sheet in silk.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [1]
[Total: 10]
14
7 A mixture of amino acids may be separated using electrophoresis. A typical practical set-up For
is shown in the diagram. Examiner’s
Use
d.c. power supply
+ –
electrolyte glass slides
amino acid mixture placed here filter paper soaked in buffer solution
(a) When the power supply is switched on, some amino acids may not move, but remain
stationary. Suggest an explanation for this observation.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) The amino acid glycine has the formula H2NCH2CO2H. Identify the species formed on
the filter paper if glycine moves to the left (positive) end of the filter paper.
.................................................................. [1]
(c) The following result was obtained from another electrophoresis. What can be deduced
about the relative sizes of, and charges on, the amino acid species A, B and C?
+ –
A B C
mixture placed here
amino acid relative size charge
[3]
© UCLES 2010 9701/42/M/J/10
15
(d) The sequence of amino acids in a polypeptide may be determined by partial hydrolysis For
of the chain into smaller pieces, often tripeptides. Examiner’s
Use
(i) Following such a partial hydrolysis, the following tripeptides were obtained from a
given polypeptide.
ala-gly-asp gly-ala-gly lys-val-ser ser-ala-gly val-ser-ala
Given that the N-terminal amino acid is lysine (lys) suggest the amino acid sequence
of the shortest polypeptide that would give the above tripeptides.
..................................................................................................................................
The structural formulae of the amino acids in the polypeptide are given below.
abbreviation amino acid structural formula
ala alanine H2NCH(CH3)CO2H
asp aspartic acid H2NCH(CH2CO2H)CO2H
gly glycine H2NCH2CO2H
lys lysine H2NCH(CH2CH2CH2CH2NH2)CO2H
ser serine H2NCH(CH2OH)CO2H
val valine H2NCH(CH(CH3)2)CO2H
(ii) Which of the tripeptides in (i) has the lowest Mr?
..........................................................................
(iii) Select one amino acid from those listed in the table which contains an ionic
side-chain at pH 8.
..........................................................................
[4]
[Total: 10]
16
8 The design and development of batteries has been a major research area in recent years. For
Examiner’s
(a) Lead-acid batteries, used in cars, are made up of a number of rechargeable cells in Use
series, and were first developed in 1860. They have the disadvantage of a relatively high
mass compared to the energy stored. During discharge, the electrode reactions in the
cells of these batteries are as follows.
I Pb + SO42– J PbSO4 + 2e–
II PbO2 + 4H+ + SO42– + 2e– J PbSO4 + 2H2O
State which of these reactions occurs at the positive electrode in a lead-acid cell during
discharge, explaining your answer.
..........................................................................................................................................
...................................................................................................................................... [1]
(b) Use the Data Booklet and the equations I and II above to calculate the voltage produced
by a lead-acid cell under standard conditions.
[2]
(c) Nickel-metal hydride batteries were developed in the 1980s and have become
increasingly common particularly for small devices such as mobile phones and digital
cameras that need near-constant sources of electrical energy. These cells use nickel
oxohydroxide (NiO(OH)) as one electrode and a hydrogen-absorbing alloy such as LiNi5
as the other electrode.
One reaction that takes place in these batteries is
NiO(OH) + H2O + e– Ni(OH)2 + OH–
(i) State the oxidation state of nickel in NiO(OH). .....................
(ii) Suggest a likely advantage of these batteries compared with lead-acid batteries.
..................................................................................................................................
..................................................................................................................................
[2]
© UCLES 2010 9701/42/M/J/10
17
(d) Hydrogen fuel cells have been suggested as the next major advance in electrically For
powered vehicles. In these fuel cells hydrogen is oxidized to produce water, using a Examiner’s
catalyst and inert electrodes. Use
(i) Suggest a material for the electrodes.
..........................................................................
(ii) Use your knowledge of hydrogen to suggest a disadvantage of these fuel cells in
powering vehicles.
..................................................................................................................................
..................................................................................................................................
[2]
(e) Many of the world’s countries are developing ways of recycling materials which are
valuable or which require large amounts of energy to produce.
For each of the following recyclable materials, state whether recycling of this material is
important in saving energy or in saving resources. Use your knowledge of chemistry to
explain each choice.
glass ................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
steel .................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
plastics .............................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[3]
[Total: 10]
© UCLES 2010 9701/42/M/J/10
18
BLANK PAGE
© UCLES 2010 9701/42/M/J/10
19
BLANK PAGE
© UCLES 2010 9701/42/M/J/10
20
BLANK PAGE
© UCLES 2010 9701/42/M/J/10
Candidate
Centre Number Number
Candidate Name

CHEMISTRY 9701/4
PAPER 4
OCTOBER/NOVEMBER SESSION 2002
1 hour
Candidates answer on the question paper.

Additional materials:
Data Booklet.
TIME 1 hour
INSTRUCTIONS TO CANDIDATES
Write your answers in the spaces provided on the question paper.
INFORMATION FOR CANDIDATES

TOTAL
This question paper consists of 11 printed pages and 1 blank page.

(NH/CG) S14878/4
© CIE 2002 [Turn over
2 For
Examiner’s
Use
1 (a) The following diagram shows the apparatus needed to measure the standard electrode
potential of copper. In the spaces below, identify or describe what the three letters A–C
represent.
A
H2, 1 atm, 298 K copper
B
platinum black 1.0 mol dm–3

CuSO4(aq)
C
A .......................................................................................................................................
B .......................................................................................................................................
C .......................................................................................................................................
[3]
(b) A student wishes to measure the standard electrode potential of the Fe3+ / Fe2+
electrode. In the space below, draw and label the set-up for the right-hand beaker
that would replace the one shown in the diagram above.
[2]
(c) Predict how the E of the Fe3+ / Fe2+ electrode would vary as
(i) the [Fe3+] is increased,
...................................................................................................................................
(ii) the [Fe2+] is increased.
...................................................................................................................................
[1]
9701/4 O/N/02
3 For
Examiner’s
Use
(d) An aqueous solution of iron(III) chloride is used to dissolve the excess of copper metal
from printed-circuit boards.
Use the half-equations and E –o values in the Data Booklet to
(i) write an equation for this reaction,
...................................................................................................................................
(ii) calculate the E –o cell for the reaction.
...................................................................................................................................
[2]
(e) The solution resulting from dissolving the copper from a small printed-circuit board was
acidified and titrated with 0.0200 mol dm–3 KMnO4. A volume of 75.0 cm3 was required
for the end point.
The equation for the titration reaction is as follows.

5Fe2+ + MnO4– + 8H+ → 5Fe3+ + Mn2+ + 4H2O
Calculate
(i) the number of moles of Fe2+ in the solution,
(ii) the mass of copper that had dissolved from the printed-circuit board.
[4]
[Total: 12]
9701/4 O/N/02 [Turn over
4 For
Examiner’s
Use
2 (a) Write an equation to represent the lattice energy of sodium oxide, Na2O.
......................................................................................................................................[1]
(b) The Born-Haber cycle shown may be used to calculate the lattice energy of sodium
oxide.
2Na+(g) + O2–(g)
2
2Na+(g) + B
∆Hat(oxygen)
+ 1
2Na (g) + /2O2(g)
3
1
1
A + /2O2(g)
2∆Hat(Na)
2Na(s) + 1/2O2(g)
4
Na2O(s)
(i) In the spaces below, identify the species A and B in the cycle, including the
appropriate state symbols.
species A ................................... species B ...................................
(ii) Identify the enthalpy changes labelled by the numbers 1 to 4 in the cycle.
1 ................................................................................................................................
2 ................................................................................................................................
3 ................................................................................................................................
4 ................................................................................................................................
[3]
9701/4 O/N/02
5 For
Examiner’s
Use
(c) Use your cycle, the following data, and further data from the Data Booklet to calculate a
value for the lattice energy of sodium oxide.
Data: enthalpy change of atomisation for Na(s) +107 kJ mol–1

first electron affinity of oxygen –141 kJ mol–1
second electron affinity of oxygen +798 kJ mol–1
enthalpy change of formation of Na2O(s) –414 kJ mol–1
enthalpy change of atomisation for oxygen = half the bond energy for O2.
[3]
(d) (i) How would you expect the magnitude of lattice energy of magnesium oxide to
compare with that of sodium oxide? Explain your reasoning.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) State a use of magnesium oxide, and explain how the use relates to your answer in
part (d) (i).
...................................................................................................................................
...................................................................................................................................
[4]
[Total: 11]
6 For
Examiner’s
Use
3 (a) (i) On the following axes, sketch the variation in melting points of the elements in
Goup IV.
melting
point
C Si Ge Sn Pb
[2]
(ii) Explain how this variation in melting point is related to the structure and bonding of
the elements.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...............................................................................................................................[2]
(b) CCl4 and SiCl4 behave differently with water.
(i) Describe the reaction (if any) of CCl4 with water.
...................................................................................................................................
(ii) Describe the reaction (if any) of SiCl4 with water.
...................................................................................................................................
(iii) Write equations for any reactions that occur.
...................................................................................................................................
...................................................................................................................................
(iv) Explain why these two chlorides differ in their behaviour with water.
...................................................................................................................................
...................................................................................................................................
[4]
[Total: 8]
9701/4 O/N/02
7 For
Examiner’s
Use
4 (a) The melting point and density of a typical transition element such as iron differ from
those of a typical s-block element such as calcium. Describe and explain these
differences.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(b) Suggest a reason why iron forms compounds containing Fe3+ ions as well as
compounds containing Fe2+ ions, whereas calcium only forms compounds containing
Ca2+ ions.
..........................................................................................................................................
......................................................................................................................................[1]
(c) An important ore of iron is siderite, iron(II) carbonate. The first step in converting it into
iron is to heat it in air. When heated in air, both calcium carbonate and iron(II) carbonate
decompose, but in different ways.
(i) Write an equation to represent the thermal decomposition of calcium carbonate.
...................................................................................................................................
(ii) When siderite is heated in air, carbon dioxide is evolved and iron(III) oxide, Fe2O3,
is left.
Construct an equation for this reaction.
...................................................................................................................................
(iii) Calculate how much iron(III) oxide can be obtained by heating 10 tonnes of
siderite.
...................................................................................................................................
...................................................................................................................................
[4]
[Total: 8]
8 For
Examiner’s
Use
5 Benzene can be converted into nitrobenzene by a nitration reaction.
NO2
(a) State the reagents and conditions necessary to carry out this reaction.
..........................................................................................................................................
......................................................................................................................................[2]
(b) What type of reaction mechanism is this?
......................................................................................................................................[1]
(c) The reaction proceeds via two steps:
+ X+ NO2 + Z+
(i) Draw the structure of the intermediate Y in the box.
(ii) Identify the cation X+..................................................................................................
(iii) Identify the cation Z+ ..................................................................................................
(iv) Write an equation to show how X+ is produced from the reagents.
...................................................................................................................................
[5]
9701/4 O/N/02
9 For
Examiner’s
Use
(d) Some aromatic poly-nitro compounds are used in perfumes as artificial musks. An
example is ‘Baur musk’.
CH3
O2N NO2
C(CH3)3
NO2
Baur musk
(i) Draw the structural formula of the hydrocarbon that could be nitrated in order to
produce Baur musk.
(ii) Suggest the structural formula of the compound formed by reacting Baur musk with
an excess of tin and concentrated hydrochloric acid.
[2]
[Total: 10]
10 For
Examiner’s
Use
6 Amides can be made by reacting amines with acyl chlorides, as in the example below.
CH3CH2COCl + H2NCH2CH2CH3 → CH3CH2CONHCH2CH2CH3 + HCl
(a) What type of reaction mechanism is this?
......................................................................................................................................[1]
(b) What compound could CH3CH2COCl be made from, and what reagent would you use?
..........................................................................................................................................
......................................................................................................................................[2]
(c) The amine CH3CH2CH2NH2 can be made from CH3CH2Br in two steps.
I II
CH3CH2Br CH3CH2CH2NH2
(i) Draw the structural formula of the intermediate in the box provided.
...................................................................................................................................
(ii) State the reagents and conditions for step I.
...................................................................................................................................
(iii) State the reagents and conditions for step II.
...................................................................................................................................
[4]
9701/4 O/N/02
11 For
Examiner’s
Use
(d) Kevlar is a low weight, high strength polyamide used as a reinforcement in car tyres,
aircraft wings and in bullet-proof vests. A portion of its chain is shown below.
NH NH–CO CO–NH NH
(i) What type of polymerisation produces Kevlar?
...................................................................................................................................
(ii) Draw the structural formulae of the monomers from which Kevlar is made.
(iii) Suggest a reason why Kevlar is much stronger than most other polyamides.
...................................................................................................................................
(iv) What reaction conditions are needed to break the amide bonds in Kevlar?
...................................................................................................................................
[4]
[Total: 11]
9701/4 O/N/02
12
BLANK PAGE
9701/4 O/N/02

CHEMISTRY 9701/04
October/November 2003
1 hour

3

provided.
TOTAL

SP (SLC/SLC) S33029/5
2 For
Examiner’s
Use
1 The reaction between iodine and propanone is catalysed by hydrogen ions.
H+
CH3COCH3 + I2 → CH3COCH2I + HI
The reaction is found to be first order with respect to [CH3COCH3] and with respect to [H+],
and zero order with respect to [I2].
(a) What do you understand by the term order of reaction?
..........................................................................................................................................
......................................................................................................................................[1]
(b) Construct a rate equation for the reaction.
......................................................................................................................................[1]
The following sketches show three ways in which the concentration of reagents might vary
during the reaction.
[reactant] [reactant] [reactant]
time time time
A B C
(c) Which of the above graphs correctly describes how the concentration of reactant
changes with time for
(i) the propanone concentration, _____________________
(ii) the iodine concentration? _____________________

[2]
9701/4/O/N/03
3 For
Examiner’s
Use
(d) When carried out in 0.1 mol dm–3 HCl solution, the rate was found to be
0.002 mol dm–3 s–1. Predict the rate of reaction in 0.2 mol dm–3 HCl and in
0.3 mol dm–3 HCl solution. Plot your figures on the following graph, and draw a line
through the points.
0.010
0.008
rate / mol dm–3 s–1
0.006
0.004
0.002
0
0 0.1 0.2 0.3
[HCl] / mol dm–3
[2]
(e) Only one of the following outline reaction mechanisms is consistent with the observed
kinetics.
I2 + H+
A
冦 → intermediate
intermediate + CH3COCH3 → products
[slow]
[fast]
CH3COCH3 + H+ →
B
冦 intermediate + I2 →
intermediate
products
[slow]
[fast]
CH3COCH3 + H+ →
C
冦 intermediate + I2 →
intermediate
products
[fast]
[slow]
CH3COCH3 + I2 →
D
冦 intermediate + H+ →
intermediate
products
[slow]
[fast]
Decide which mechanism is consistent, explaining the reasons for your choice.
Mechanism letter (A, B, C or D) _____________________
Reasons
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
9701/4/O/N/03 [Turn over
4 For
Examiner’s
Use
(f) When the starting concentrations of propanone, iodine and H+ were 0.20 mol dm–3,
0.01 mol dm–3 and 0.5 mol dm–3 respectively, the rate of decrease of [I2] was found to
be 3.3 x 10–6 mol dm–3 s–1.
(i) Suggest a method you could use to measure [I2].
...................................................................................................................................
(ii) Use these figures and your rate equation in part (b) to calculate a value for the rate
constant k.
...................................................................................................................................
(iii) What are the units of k?
...................................................................................................................................
[3]
[Total : 12]
2 (a) Methanoic acid, HCO2H, is a weak acid, with Ka = 1.77 x 10–4 mol dm–3.
(i) Write an expression for the Ka of methanoic acid.
...................................................................................................................................
–3
(ii) Use your expression to calculate the [H+] in a 0.0500 mol dm solution of
methanoic acid.
...................................................................................................................................
(iii) Calculate the percentage of HCO2H molecules that are ionised in this solution.
(iv) Calculate the pH of this solution.
...................................................................................................................................
[4]
9701/4/O/N/03
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(b) Calculate the pH of a 0.0500 mol dm–3 solution of the strong acid HCl.
......................................................................................................................................[1]
(c) Both HCO2H and HCl react with powdered magnesium metal, giving off hydrogen gas.
For a fixed amount of magnesium, the rate equation for the reaction is as follows.
rate = k [H+(aq)]
(i) Write an equation for the reaction between HCO2H and Mg.
...................................................................................................................................
When 20.0 cm3 of a 0.0500 mol dm–3 solution of either acid is reacted with an excess of
powdered magnesium, the same volume of hydrogen is given off, but the methanoic
acid solution reacts much more slowly than the hydrochloric acid.
(ii) Calculate the volume of hydrogen given off.
...................................................................................................................................
(iii) Explain why the hydrogen is evolved more slowly from the methanoic acid solution.
...................................................................................................................................
...................................................................................................................................
(iv) Explain why, eventually, the methanoic acid solution produces just as much
hydrogen as the hydrochloric acid solution.
...................................................................................................................................
...................................................................................................................................
...............................................................................................................................[5]
[Total : 10]
6 For
Examiner’s
Use
3 Potassium manganate(VII) and potassium dichromate(VI) are both used as oxidising
agents in acidic solution.
(a) Using data from the Data Booklet, write either ionic or full equations for the reaction
between
(i) KMnO4 and FeSO4 in dilute H2SO4,
(ii) K2Cr2O7 and SO2 in dilute H2SO4.
[3]
(b) KMnO4 is often used in titrations to estimate reducing agents. It is added from a burette
to a solution of the reducing agent.
(i) What colour is KMnO4 solution?
...................................................................................................................................
(ii) How is the end point in the titration recognised?
...................................................................................................................................
(iii) A solution of 0.010 mol dm–3 KMnO4 was used to estimate the amount of FeSO4 in
an iron dietary supplement tablet. The tablet was crushed under dilute H2SO4 and
the KMnO4 solution was added from the burette. It was found that 14.00 cm3 were
required.
Calculate the mass of FeSO4 in the tablet.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[5]
9701/4/O/N/03
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(c) Patients are prescribed iron dietary supplement tablets to cure anaemia, which is a
deficiency of haemoglobin in the blood.
(i) Describe the function of haemoglobin, and how the iron atoms it contains carry out
that function.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) Explain why even a small amount of carbon monoxide in the bloodstream is
poisonous.
...................................................................................................................................
...................................................................................................................................
[3]
[Total : 11]
8 For
Examiner’s
Use
4 Ethyl 4-hydroxybenzoate, E, is a permitted food preservative.
HO CO2C2H5
(a) Name two functional groups in E.
..........................................................................................................................................
......................................................................................................................................[2]
(b) Draw the structures of the compounds formed when E reacts with
(i) sodium metal,
(ii) NaOH(aq) under reflux,
(iii) Br2(aq).
[4]
9701/4/O/N/03
9 For
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(c) Compounds F and G are isomers of E.
HOCH2 CO2CH3 CH3CH2O CO2H
F G
(i) Suggest the order of acid strength of E, F and G.
...................................................................................................................................
...................................................................................................................................
(ii) Based on their relative acidities, suggest how samples of E, F and G could be
distinguished from each other by the use of NaOH(aq) and Na2CO3(aq).
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[3]
[Total : 9]
10 For
Examiner’s
Use
5 The amino acid alanine, K, can be obtained from 2-hydroxypropanoic acid, H, by the
following route.
I II
CH3CH(OH)CO2H → CH3CHClCO2H → CH3CH(NH2)CO2H
H J K
(a) Suggest a test you could use to distinguish H from its isomer 3-hydroxypropanoic acid, L.
HOCH2CH2CO2H
L
reagents ...........................................................................................................................
observation with H ............................................................................................................
observation with L ........................................................................................................[2]
(b) How would the acidity of chloropropanoic acid, J, compare with that of propanoic acid?
Briefly explain your answer.
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[2]
(c) Alanine reacts with both acids and bases.
Write an equation for the reaction between alanine and sodium hydroxide, drawing the
displayed formula of the organic product.
[2]
(d) In solution, alanine exists as a zwitterion. Draw the structure of this ion.
[1]
9701/4/O/N/03
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(e) Alanine is one of about 20 amino acids that make up proteins.
(i) What type of bond joins amino acids together in proteins?
...................................................................................................................................
(ii) Draw the displayed formula of the compound formed when two alanine molecules
are joined by this bond.
[2]
(f) An excess of benzoic acid in the body (present as a preservative in many foodstuffs, or
formed by oxidation of aromatic compounds present in food) is excreted as hippuric
acid, M.
CONHCH2CO2H
(i) Suggest a reagent that could be reacted with glycine in the laboratory to form
hippuric acid.
...................................................................................................................................
(ii) Suggest the reagents and conditions needed to re-form glycine from hippuric acid.
...................................................................................................................................
...................................................................................................................................
[3]
[Total : 12]
12 For
Examiner’s
Use
6 Many millions of tonnes of limestone, CaCO3, are quarried each year for use in the steel
industries of the world, and in agriculture. For use in agriculture, the limestone is often
decomposed by heating it in limekilns, and then adding water.
(a) Write balanced equations representing the following two processes.
(i) heating limestone
...................................................................................................................................
(ii) then adding water
...................................................................................................................................
[2]
(b) Describe the agricultural use of the product of this process.
..........................................................................................................................................
..........................................................................................................................................
[1]
(c) Describe and explain the trend observed in the thermal stabilities of the carbonates of
Group II.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[3]
[Total : 6]
9701/4/O/N/03

CHEMISTRY 9701/04
1 hour 15 minutes

4

provided.
Total

SPA (SJF3046/GR) S61559/4
2 For
Examiner’s
Use
1 Sulphuric acid is a strong dibasic acid, which ionises in solution as follows.
H2SO4(aq) 2H+(aq) + SO42–(aq)
(a) The organic base guanidine contains carbon, nitrogen and hydrogen. Its reaction with
acids can be represented as follows.
B(aq) + H+ (aq) BH+(aq)
where B represents the molecule of guanidine.
When a 25.0 cm3 sample of dilute sulphuric acid was titrated against a solution of
guanidine, the following titration curve was obtained.
14
pH
0
0 10 20 30 40 50 60 70
Volume of guanidine added / cm3
Use this curve to answer the following questions.
(i) Is guanidine a strong or a weak base? Explain your answer.
...................................................................................................................................
...................................................................................................................................
(ii) The pH at the start of the titration was 0.70. Calculate the [H+], and hence the
concentration of sulphuric acid, at the start of the titration.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
© UCLES 2004 9701/04/O/N04
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(iii) Calculate the concentration of guanidine in the solution in mol dm–3.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(iv) The guanidine solution contained 8.68 g of the base per dm3. Use your answer to
(iii) calculate the Mr of guanidine.
.............................................................................................................................. [6]
(b) One of the major industrial uses of sulphuric acid is to convert phosphate rock (calcium
fluorophosphate(V)) into ‘superphosphate’ for use as a fertiliser. The process can be
represented by the following partially balanced equation.
2 Ca5(PO4)3F + 7H2SO4 → ....... CaSO4 + ....... Ca(H2PO4)2 + ....... HF

‘superphosphate’
(i) Balance the above equation.
(ii) Use your balanced equation to calculate the mass of H2SO4 required to
manufacture 1.0 kg of superphosphate fertiliser.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
.............................................................................................................................. [4]
(c) Solutions of hydrogenphosphates make useful buffers for biochemical experiments.
H2PO4– HPO42– + H+
(i) Explain what is meant by the term buffer solution.
...................................................................................................................................
...................................................................................................................................
(ii) Calculate the pH of a buffer solution that contains 0.20 mol dm–3 NaH2PO4 and
0.10 mol dm–3 Na2HPO4. [Ka (H2PO4–) = 6.3 x 10–8 mol dm–3]
...................................................................................................................................
...................................................................................................................................
.............................................................................................................................. [3]
[Total: 13]
© UCLES 2004 9701/04/O/N04 [Turn over
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2 The diagram shows a laboratory illustration of a simple hydrogen-oxygen fuel cell.
oxygen gas at hydrogen gas at

1 atmosphere 1 atmosphere
salt bridge
solution of solution of
hydrochloric acid: hydrochloric acid:
[H3O+] = 1 mol dm-3 [H3O+] = 1 mol dm-3
inert electrodes
(a) Write the half equation for the reaction occurring at the left hand (oxygen) electrode
when the cell operates.
..........................................................................................................................................
..................................................................................................................................... [1]
(b) State the polarity (+ or –) of the left hand (oxygen) electrode. ..................................... [1]
(c) Use the Data Booklet to calculate the voltage produced by this cell.
..................................................................................................................................... [1]
(d) Only a very small current can be drawn from this laboratory cell. Suggest one way in
which it could be modified to enable a larger current to be drawn from it.
..........................................................................................................................................
..................................................................................................................................... [1]
(e) A fuel cell in an orbiting satellite is required to produce a current of 0.010 A for 400 days.
Calculate the mass of hydrogen that will be needed.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
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(f) State one advantage, and one disadvantage of using fuel cells to power road vehicles
compared to hydrocarbon fuels such as petrol.
advantage: .......................................................................................................................
..........................................................................................................................................
disadvantage: ...................................................................................................................
..................................................................................................................................... [2]
[Total: 9]
3 Calcium sulphate is a major by-product of flue gas desulphurisation, which is an important

method of decreasing the emission of acid-rain gases from power stations. It is used
extensively in plaster and cement. Both magnesium sulphate and barium sulphate find uses
in medicine.
Describe and explain the variation in the solubilities of the Group II sulphates in water.
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
..................................................................................................................................................
............................................................................................................................................. [4]
[Total: 4]
6 For
Examiner’s
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4 (a) Explain what is meant by the term transition element.
..........................................................................................................................................
..................................................................................................................................... [1]
(b) (i) How do the atomic radii of the transition elements vary from chromium to copper?
...................................................................................................................................
(ii) Predict, with a reason, the variation in the densities of the transition elements from
chromium to copper.
...................................................................................................................................
.............................................................................................................................. [3]
(c) Complete the following electronic configuration of the Cu2+ ion.
1s22s22p63s23p6 [1]
(d) Copper ions in aqueous solution are pale blue, due to the formation of a complex ion.
(i) Explain what is meant by the term complex ion.
...................................................................................................................................
...................................................................................................................................
(ii) Draw the structure of the complex ion formed in a solution of Cu2+(aq).
[2]
© UCLES 2004 9701/04/O/N04
7 For
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(e) When dilute aqueous ammonia is added to a solution of Cu2+(aq), the colour changes
as a new complex ion is formed.
(i) State the colour of the new complex .........................................................................
(ii) Write an equation showing the formation of the new complex.
.............................................................................................................................. [2]
(f) When concentrated hydrochloric acid is added to a solution of Cu2+(aq), the colour
changes to yellow-green. On adding water, the colour returns to pale blue.
Suggest an explanation for these changes.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
[Total: 12]
8 For
Examiner’s
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5 This question is concerned with organochlorine compounds.
(a) State the conditions needed to produce the two compounds A and B.
CH3 CH3 CH2Cl
Cl2 Cl2
Cl
A B
(i) conditions for reaction I
...................................................................................................................................
(ii) conditions for reaction II
.............................................................................................................................. [2]
(b) State the reagent needed to carry out the following reaction.
CO2H COCl
reaction III
reagent for reaction III: ................................................................................................. [1]
© UCLES 2004 9701/04/O/N04
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(c) The three chloro-compounds A, B and C vary in their ease of hydrolysis.
(i) Place a tick in the box corresponding to the correct relative rates of hydrolysis.
[the symbol ‘>’ means ‘faster than’]
place one
tick only in
this column
A>B>C
A>C>B
B>A>C
B>C>A
C>B>A
C>A>B
(ii) Suggest an explanation for these differences in reactivity.
...................................................................................................................................
...................................................................................................................................
.............................................................................................................................. [3]
10 For
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(d) Draw the structural formulae of the organic products of the following reactions of
compound C.
OH in NaOH (aq)
COCl
CH3NH2
H 2O
[3]
[Total: 9]
© UCLES 2004 9701/04/O/N04
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6 Compounds D and E are both ketones.
CH3CH2COCH2CH3 CH3CH2CH2COCH3
D E
(a) State which one of these compound reacts with alkaline aqueous iodine, and draw the
structural formulae of the products formed during this reactions.
(i) compound (D or E) ....................................................................................................
(ii) products
.............................................................................................................................. [3]
(b) The reduction of D with NaBH4 produces just one alcohol, but a similar reduction of E
produces two isomers in equal amounts. Explain these observations, drawing structures
where appropriate.
..........................................................................................................................................
..........................................................................................................................................
[3]
[Total: 6]
12 For
Examiner’s
Use
7 Both phenol and phenylamine react similarly with aqueous bromine.
(a) State two observations you would make when these reactions take place.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(b) Describe a simple test-tube reaction you could use to distinguish between phenol and
phenylamine.
..........................................................................................................................................
......................................................................................................................................[1]
(c) The compound 3-aminobenzoic acid can be prepared by the following series of
reactions.
CH3 CO2H CO2H CO2H
reaction IV reaction V reaction VI
NO2 NH2
Suggest suitable reagents and conditions for
reaction IV, .......................................................................................................................
reaction V, ........................................................................................................................
reaction VI. .................................................................................................................. [4]
[Total: 7]
Every reasonable effort has been made to trace all copyright holders where the publishers (i.e. UCLES) are aware that third-party material has been reproduced.
The publishers would be pleased to hear from anyone whose rights they have unwittingly infringed.
© UCLES 2004 9701/04/O/N04

CHEMISTRY 9701/04
1 hour 15 minutes


1
2

provided.
TOTAL

SPA (MML 8078 3/04) S77894/4
2 For
Examiner’s
Use
1 Silver bromide, AgBr, is widely used in photography. In a photographic film, AgBr crystals
are precipitated into a gelatine base as ‘grains’ of diameter about 1 × 10–6 m.
(a) Calculate the approximate number of silver ions contained in a grain of AgBr of mass
2.5 × 10–12 g.
..........................................................................................................................................
.................................................................................................................................... [2]
(b) AgBr is only sparingly soluble in water. The [Ag+] in a saturated solution of AgBr can
be estimated by measuring the Ecell of the following cell.
H2(g), 1 atm, 298 K C
salt bridge
D
A
[Ag+(aq)] = x mol dm–3
(i) In the spaces below, identify what the four letters A – D in the above diagram
represent.
A .................................................... C ....................................................
B .................................................... D ....................................................
(ii) Predict how the potential of the right hand electrode might vary as [Ag+] is
decreased.
..................................................................................................................................
In its saturated solution, [AgBr(aq)] = 7.1 × 10–7 mol dm–3.
(iii) Write an expression for the solubility product of AgBr, and calculate its value,
including units.
..................................................................................................................................
..................................................................................................................................
[7]
© UCLES 2005 9701/04/O/N/05
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Examiner’s
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(c) (i) Write a chemical equation representing the lattice energy of AgBr.
..................................................................................................................................
(ii) Use the following data to calculate a value for the lattice energy of AgBr(s).
first ionisation energy of silver = +731 kJ mol–1
electron affinity of bromine = –325 kJ mol–1
enthalpy change of atomisation of silver = +285 kJ mol–1
enthalpy change of atomisation of bromine = +112 kJ mol–1
enthalpy change of formation of AgBr(s) = –100 kJ mol–1
..................................................................................................................................
(iii) How might the lattice energy of AgCl compare to that of AgBr? Explain your
answer.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
In photography a bromide ion absorbs a photon and releases an electron which reduces a
silver ion to a silver atom.
Br – → Br + e–
Ag+ + e– → Ag
(d) Predict whether it would require more energy or less energy to initiate this process in
a AgCl emulsion, compared to a AgBr emulsion. Explain your answer.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [1]
[Total: 14]
© UCLES 2005 9701/04/O/N/05 [Turn over
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2 (a) What do you understand by the term standard electrode potential?
..........................................................................................................................................
.................................................................................................................................... [2]
(b) By reference to relevant E data in the Data Booklet, explain how the halogen/halide
electrode potentials relate to the relative reactivity of the halogens as oxidising agents.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
(c) Use data from the Data Booklet to construct redox equations, and calculate the
standard cell potentials, for the reactions between
(i) Acidified H2O2(aq) and KI(aq),
..................................................................................................................................
(ii) Cl 2(aq) + SO2(aq).
..................................................................................................................................
[4]
(d) Use data from the Data Booklet to predict the likely product of the reaction between
I2(aq) and tin metal, writing a balanced equation for the reaction.
.................................................................................................................................... [2]
[Total: 10]
© UCLES 2005 9701/04/O/N/05
5
BLANK PAGE
6 For
Examiner’s
Use
3 (a) (i) Use the following sets of axes to sketch graphs of the variations in the melting
points and the electrical conductivities of the Group IV elements.
melting point electric conductivity
high high
medium medium
low low
C Si Ge Sn Pb C Si Ge Sn Pb
(ii) Explain how the variation in conductivity is related to the structure and bonding in
the elements.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[6]
(b) Going down Group IV there is a variation in the relative stabilities of the higher and
lower oxidation states of the elements in their oxides.
Illustrating your answers with balanced chemical equations, in each of the following
cases suggest one piece of chemical evidence to show that
(i) CO is less stable than CO2,
..................................................................................................................................
..................................................................................................................................
(ii) PbO is more stable than PbO2.
..................................................................................................................................
..................................................................................................................................
[3]
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(c) Name one ceramic based on silicon(IV) oxide, and explain what properties of the
oxide make it suitable for this use.
..........................................................................................................................................
.................................................................................................................................... [1]
(d) Tin(II) oxide reacts with both acids and alkalis.
(i) What name is given to this property of an oxide?
..................................................................................................................................
(ii) Write suitable equations to show these two reactions of tin(II) oxide.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 13]
8 For
Examiner’s
Use
4 Rodinol is used as a photographic developer. In alkaline solution it is a mild reducing agent,
providing electrons according to the following half equation.
OH O
+ 2 OH– + H2O + NH3 + 2e–
E = +0.65 V
NH2 O
rodinol
Rodinol ‘develops’ a latent photographic image by reducing activated silver bromide grains
to silver metal and bromide ions.
(a) Construct a balanced equation for the reaction between rodinol and AgBr.
.................................................................................................................................... [1]
(b) Suggest, with a reason, how the basicity of rodinol might compare to that of ammonia.
..........................................................................................................................................
..........................................................................................................................................
.................................................................................................................................... [2]
(c) Suggest structural formulae for the compounds E, F and G in the following chart of the
reactions of rodinol.
NaOH
OH
E
HCl
NH2 F
Br2(aq)
rodinol
[3]
© UCLES 2005 9701/04/O/N/05
9 For
Examiner’s
Use
(d) Rodinol can be synthesised from phenol by the following route.
OH OH OH
I II
NO2 NH2
(i) Suggest reagents and conditions for step I.
..................................................................................................................................
(ii) What type of reaction is step II?
..................................................................................................................................
(iii) Place a tick in the box by the most suitable reagent for step II.
(place a tick in one box only)
H 3O+ + heat
OH–(aq) + heat
Cr2O72– + H+ + heat
HNO3(aq)
Sn + HCl (aq)
NH3 in ethanol + heat/pressure

[3]
(e) Rodinol is also an important intermediate in the commercial production of the

analgesic drug paracetamol.
OH OH
NH2 NHCOCH3
paracetamol
(i) Name two functional groups in paracetamol.
..................................................................................................................................
..................................................................................................................................
(ii) Suggest a reagent to convert rodinol into paracetamol.
..................................................................................................................................
[3]
[Total: 12]
10 For
Examiner’s
Use
5 Hydrophilic polymers find important uses in the manufacture of contact lenses and wound
dressings. Their chemical structures allow them to bond with water molecules, which keeps
them soft and flexible. Sections of two hydrophilic polymers are shown below.
OH OH OH OH
CH CH CH CH
C C C C
H2 H2 H2 H2
OH O
H H2 H2
N CH C C C
C CH N CH N
H H
O OH OH
(a) What type of polymerisation has produced
(i) polymer H? ...................................................
(ii) polymer J? ....................................................

[2]
(b) What type of attractions might occur between these polymers and molecules of water?
.................................................................................................................................... [1]
(c) Chains of polymer H can be ‘cross-linked’, i.e. joined together, by reaction with a small
bifunctional molecule.
(i) Which one of the following molecules would be most suitable for such cross-
linking?
(place a tick in one box only)
HOCH2CH2OH
H2NCH2CH2NH2
HOCH2CH2CO2H
HO2CCH2CH2CO2H
H2NCH2CH2CO2H
(ii) What type of bond would be formed during the cross-linking?
..................................................................................................................................
[2]
© UCLES 2005 9701/04/O/N/05
11 For
Examiner’s
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(d) (i) Suggest the reagents and conditions needed to hydrolyse polymer J into its
monomers.
..................................................................................................................................
(ii) Draw the structural formulae of the two products of this hydrolysis reaction.
..................................................................................................................................
[3]
(e) The last compound in the list in (c)(i) above is 3-aminopropanoic acid. This can be
made from potassium chloroethanoate by the following 3-stage route.
KCN stage II
ClCH2CO2– K+ H2NCH2CH2CO2– K+
stage III
H2NCH2CH2CO2H
(i) In the box above write the structure of the intermediate in this route.
stage II .....................................................................................................................
stage III ....................................................................................................................

[3]
[Total: 11]
© UCLES 2005 9701/04/O/N/05
12
BLANK PAGE
9701/04/O/N/05

CHEMISTRY 9701/04
1 hour 15 minutes


1
Total

SPA (SJF3730) T02141/3
2 For
Examiner’s
Use
1 (a) Describe and explain how the boiling points of the tetrachlorides of the Group IV
elements vary down the group.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
(b) The tetrachlorides are all covalent compounds. Draw a diagram showing the shape of a
molecule of silicon tetrachloride, including values for bond angles.
[2]
(c) The noble gas xenon forms a tetrafluoride, XeF4. Only four of xenon’s outer shell
electrons are used in bonding to the fluorine atoms.
(i) Draw a dot-and-cross diagram showing how the outer-shell electrons are arranged
in XeF4.
(ii) Predict the shape and the bond angles in XeF4.
...................................................................................................................................
...................................................................................................................................
[4]
(d) Describe and explain how the reactions of CCl 4 and SiCl 4 with water differ. Write an
equation for any reaction that occurs.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
© UCLES 2006 9701/04/O/N/06
3 For
Examiner’s
Use
(e) Many tonnes of lead tetrachloride used to be produced to make the anti-knock petrol
additive tetraethyl-lead, Pb(C2H5)4, by the following reaction.
PbCl4 + ………… Na + ………… C2H5Cl ⎯⎯→ Pb(C2H5)4 + ………… NaCl
Balance this equation and use it to calculate the mass of sodium needed to produce
1.0 kg of tetraethyl-lead.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
[Total: 15]
4 For
Examiner’s
Use
2 Ibuprofen is one of the most commonly used non-steroidal anti-inflammatory drugs, used to
treat chronic arthritic pain caused by inflammation of the joints.
CH3
CH3 CH O
C
CH
CH3 CH2 OH
ibuprofen
(a) (i) Draw a circle around any chiral centre(s) in the above structure.
(ii) Write down the molecular formula of ibuprofen.
...................................................................................................................................
(iii) Calculate the Mr of ibuprofen and use it to calculate how many grams are
needed to make 100 cm3 of a 0.15 mol dm–3 solution.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(iv) Vigorous oxidation of ibuprofen produces a dibasic acid A. A solution containing

0.10 g of A required 12.0 cm3 of 0.10 mol dm–3 NaOH for neutralisation.
Suggest a structure for A, showing your working.
...................................................................................................................................
[7]
(b) The Ka value for ibuprofen is 6.3 × 10–6 mol dm–3.
(i) Write an expression for Ka.
...................................................................................................................................
(ii) Use the Ka value to calculate the pH of a 0.15 mol dm–3 solution of ibuprofen.
...................................................................................................................................
...................................................................................................................................
[3]
© UCLES 2006 9701/04/O/N/06
5 For
Examiner’s
Use
(c) To avoid problems with digestive irritation over a long period of use, research is being
carried out into ways of administering ibuprofen using skin patches. For this use the
compound is dissolved in a hydrophilic gel which acts as a buffer.
(i) What do you understand by the term buffer ?
...................................................................................................................................
...................................................................................................................................
The buffer used in the pharmaceutical preparation is a solution containing Na2HPO4

and NaH2PO4. These salts contain the HPO2– –
4 and H2PO 4 ions respectively.
(ii) Write equations to show how this buffer reacts with
H+ ions, ....................................................................................................................
OH– ions. .................................................................................................................
(iii) A buffer solution containing equal concentrations of the two sodium phosphate
salts has a pH of 7.20.
Calculate the pH of a pharmaceutical preparation containing 0.002 mol dm–3 of
Na2HPO4 and 0.005 mol dm–3 of NaH2PO4.
[5]
[Total: 15]
6 For
Examiner’s
Use
3 (a) (i) Write an equation showing the thermal decomposition of calcium nitrate, Ca(NO3)2.
...................................................................................................................................
(ii) State and explain how the thermal stabilities of the nitrates vary down Group II.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
[4]
(b) The nitrates of calcium, strontium or barium are often added to firework mixtures to
produce red or green flames. The equation for the decomposition of one such mixture is
as follows.
Sr(NO3)2(s) + 3C(s) ⎯→ SrO(s) + N2(g) + 2CO2(g) + CO(g)
Calculate the volume of gas given off (measured at room temperature and pressure)
when a 10.0 g sample of this mixture decomposes. [Mr: Sr(NO3)2, 211.6]
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(c) Explain in detail how carbon monoxide, produced in this reaction, is poisonous.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
[Total: 8]
© UCLES 2006 9701/04/O/N/06
7
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8 For
Examiner’s
Use
4 Ethylbenzene is an important starting material for making polystyrene (poly(phenylethene)).
CH2CH3 CHCl CH3 CH CH2
polystyrene
+ Cl 2
ethylbenzene B phenylethene
(a) (i) State the conditions needed to carry out reaction I in the laboratory.
...................................................................................................................................
(ii) State the reagent and conditions needed for reaction II.
...................................................................................................................................
(iii) Draw the structure of the repeat unit of polystyrene.
(iv) There are several polymers that consist of phenylethene co-polymerised with other
monomers. The following formula shows part of the chain of one such co-polymer.
CH2 CH CH2 CH CH2 CH CH2
CN CN
Deduce the structural formula of the other monomer.
[5]
© UCLES 2006 9701/04/O/N/06
9 For
Examiner’s
Use
(b) Compound B undergoes the following series of reactions.
CHCl CH3 CH(OH)CH3
reaction III reaction IV +
I2 + NaOH
B C D
(i) Suggest reagents and conditions for reaction III.
...................................................................................................................................
(ii) What would you see when reaction IV was carried out?
...................................................................................................................................
(iii) Draw structures for C and D in the boxes above.

[4]
(c) Ethylbenzene can react with chlorine under a different set of conditions to give
compound E, an isomer of compound B. Compound E undergoes the following
reaction.
CH2CH3 CO2H
reaction V reaction VI
+ Cl2
Cl
(i) Draw a structure for E in the box above.
(ii) Describe the conditions used for reaction V.
...................................................................................................................................
(iii) State the reagents used for reaction VI.
...................................................................................................................................
[3]
[Total: 12]
10 For
Examiner’s
Use
5 4-Amino-1-methylbenzene, F, is a useful starting material for making several dyes. The
following chart shows some of its reactions.
Br
CH3 NH2
reaction I Br
CH3
reaction II
+ CH3COCl
NH2
reaction III
F + HCl G
(a) (i) Suggest reagents and conditions for reaction I.
...................................................................................................................................
(ii) Draw the structural formulae of compounds G and H in the boxes above.
(iii) Name the functional group you have drawn in compound G.
...................................................................................................................................
[4]
© UCLES 2006 9701/04/O/N/06
11 For
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(b) The dye J can be made from F by the following series of reactions.
reaction IV
H3C NH2 H3C N2Cl
reaction V
F H3C
H3C N N OH
CH3
J
Suggest reagents and conditions for
(i) reaction IV, ................................................................................................................
(ii) reaction V.
...................................................................................................................................
[4]
(c) Many dyestuffs used as food colourings, such as Sunset Yellow, contain sodium
sulphonate (–SO 3–Na+) groups attached to the rings. Suggest, with an explanation, a
reason for this.
–
SO 3 Na+
HO
N
–
SO 3 Na+
Sunset Yellow
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
[Total: 10]
© UCLES 2006 9701/04/O/N/06
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9701/04/O/N/06
*5027796699*
CHEMISTRY 9701/04
Paper 4 Structured Questions October/November 2007
1 hour 45 minutes
Section A
Section B
appropriate units.
5
part question.
6
10
Total
SPA (KN) T34461/2

2 For
Examiner’s
Use
Section A
1 (a) Use the general formula of a carboxylic acid, RCO2H, to write equations to explain the
following terms.
(i) Ka .............................................................................................................................
(ii) pKa ...........................................................................................................................

[2]
(b) The pKa values of four carboxylic acids are listed in the table below.
acid formula of acid pKa
1 CH3CH2CO2H 4.9
2 CH3CHCl CO2H 2.8
3 CH3CCl2CO2H 1.4
4 CH2Cl CH2CO2H 4.1
(i) Describe and explain the trend in acid strength shown by acids 1, 2 and 3.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Suggest an explanation for the difference in the pKa values for acids 2 and 4.
..................................................................................................................................
..................................................................................................................................
(iii) Calculate the pH of a 0.010 mol dm–3 solution of propanoic acid (acid 1).
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[6]
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(c) A good way of making synthetic amino acids uses chloro-acids as intermediates.
Cl2 + trace of P NH3(excess)

CH3CH2CO2H CH3CHCl CO2H CH3CH(NH2)CO2H
I II alanine
(i) Suggest the role that the trace of phosphorus plays in reaction I.
..................................................................................................................................
(ii) Write a fully balanced equation for reaction I.
..................................................................................................................................
(iii) State the type of mechanism of reaction II.
..................................................................................................................................
(iv) When 10.0 g of propanoic acid was used in this 2-stage synthesis, a yield of 9.5 g of
alanine was obtained.
Calculate the overall percentage yield.
..................................................................................................................................
[5]
(d) In the solid state and in aqueous solutions, alanine exists as a zwitterion.
Draw the structural formula of this zwitterion.
[2]
[Total: 15]
4 For
Examiner’s
Use
2 (a) Describe and explain the trend in the solubilities of the sulphates of the Group II
elements.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[4]
(b) The salts formed by the Group II elements with other divalent anions show a similar
trend in their solubilities, whereas most of their salts with monovalent anions are very
soluble.
Use this information to predict the identities of compounds A and B in the following
description of some reactions of Group II compounds, and write balanced equations for
the reactions.
Magnesium hydroxide, Mg(OH)2, is almost insoluble in water. Stirring a mixture of

magnesium hydroxide and aqueous ethanedioic acid, H2C2O4, produces a clear
colourless solution containing A. When a solution of calcium nitrate, Ca(NO3)2, is added,
a white precipitate of B is formed.
identity of A ......................................... identity of B ........................................................
equations .........................................................................................................................
......................................................................................................................................[3]
(c) The solubility product, Ksp, of magnesium hydroxide has a numerical value of
2.0 × 10–11.
(i) Write an expression for the Ksp of magnesium hydroxide, stating its units.
..................................................................................................................................
(ii) Use the value of Ksp given to calculate the concentration of Mg(OH)2 in a saturated
solution.
..................................................................................................................................
..................................................................................................................................
(iii) Explain whether magnesium hydroxide would be more or less soluble in

0.1 mol dm–3 MgSO4(aq) than in water.
..................................................................................................................................
..................................................................................................................................
[5]
[Total: 12]
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Use
3 The following account describes the preparation of Péligot’s salt, named after the 19th century
French chemist who first made it.
Place 6.0 g of potassium dichromate(VI) in a 100 cm3 beaker and add 8.0 g of concentrated hydrochloric
acid and 1.0 cm3 water. Warm the mixture gently; if carefully done the dichromate(VI) will dissolve
without the evolution of chlorine. On cooling the beaker in an ice bath the solution will deposit long
orange-red crystals of Péligotʼs salt.
An analysis of Péligot’s salt showed that it contained the following percentages by mass:
K, 22.4%; Cr, 29.8%; Cl, 20.3%; O, 27.5%.
(a) Calculate the empirical formula of Péligot’s salt.
[2]
(b) Suggest a balanced equation for the formation of Péligot’s salt.
......................................................................................................................................[1]
(c) The instructions suggest that strong heating might cause chlorine to be evolved.
(i) What type of reaction would produce chlorine in this system?
..................................................................................................................................
(ii) Use the Data Booklet to identify relevant half equations and E o values for the
production of chlorine from the reaction between K2Cr2O7 and HCl.
..................................................................................................................................
..................................................................................................................................
Use these equations to write the overall full ionic equation for this reaction.
..................................................................................................................................
(iii) The use of dilute HCl (aq) does not result in the production of chlorine. Suggest
why this is so.
..................................................................................................................................
(iv) Use the Data Booklet to suggest a reason why it is not possible to prepare the
bromine analogue of Péligot’s salt by using HBr(aq) instead of HCl (aq).
..................................................................................................................................
[6]
[Total: 9]
6 For
Examiner’s
Use
4 (a) By choosing the chlorides of two of the Group IV elements as examples, describe the
trend in the reactions of these chlorides with water. Suggest an explanation for any
differences, and write equations for any reactions that occur.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(b) The standard enthalpy changes of formation of lead(II) chloride and lead(IV) chloride
are given in the following table.
compound ∆H of / kJ mol–1
PbCl2(s) –359
PbCl4(l) –329
Use these data, and also bond energy data from the Data Booklet, to calculate the
enthalpy changes for the following two reactions.
(i) CCl2(g) + Cl2(g) CCl4(g)
∆H o = ........................... kJ mol–1
(ii) PbCl2(s) + Cl2(g) PbCl4(l)
∆H o = ........................... kJ mol–1
(iii) Make use of your answers to parts (i) and (ii) to suggest how the relative stabilities
of the two oxidation states vary down the Group.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 6]
© UCLES 2007 9701/04/O/N/07
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Examiner’s
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5 Potassium manganate(VII) can be used to estimate the percentage of hydrogen peroxide
in household bleach. The following unbalanced equation represents the reaction between
them.
–
......... MnO 4 + ......... H2O2 + ......... H+ ......... Mn2+ + ......... H2O + ......... O2
(a) Balance this equation by putting the appropriate numbers in the spaces above. [1]
(b) Use data from the Data Booklet to calculate the E ocell for the reaction.
......................................................................................................................................[1]
(c) When 0.020 mol dm–3 KMnO4(aq) was added from a burette into an acidified 25.0 cm3
sample of H2O2, 15.0 cm3 of KMnO4 was required to reach the end-point.
(i) Describe what you would see during this titration, and also at the end-point.
..................................................................................................................................
..................................................................................................................................
(ii) Calculate the concentration of H2O2 in the sample.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 6]
8 For
Examiner’s
Use
6 The phenol 1-naphthol is a starting point for the manufacture of carbaryl, an insecticide and
a plant growth inhibitor.
CH3NH C O
OH O
+ NaOH + CH3NHCOCl
1-naphthol C carbaryl
(a) (i) Suggest a structure for the intermediate C and draw it in the box above.
(ii) Name the functional groups in carbaryl.
..................................................................................................................................
..................................................................................................................................
(iii) Suggest structures for the three products formed when carbaryl is hydrolysed.
(iv) What reagents and conditions would you use for this hydrolysis?
..................................................................................................................................
[7]
(b) Suggest reagents and conditions for converting 1-naphthol into each of the following
compounds.
(i) OH
Br
................................................................................
Br
(ii) OH
................................................................................
[2]
NO2
© UCLES 2007 9701/04/O/N/07
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(c) Compound D is an isomer of 4-nitro-1-naphthol. D is formed as a by-product during the
reaction in b(ii). It can be converted into 2-amino-1-naphthol, E.
OH
NH2
I
D E
(i) Suggest the structural formula of the isomer D.
(ii) Suggest reagents needed for reaction I.
..................................................................................................................................
(iii) Suggest the structural formula of the compound formed when compound E reacts
with an excess of CH3COCl.
[3]
(d) When an alkaline solution of compound E is added to a solution containing Cu2+(aq)

ions, a pale green-blue precipitate F forms. Analysis of F shows that its formula is
Cu(C10H8NO)2(H2O)2.
(i) Complete the following structural formula of F.
H 2O
O
Cu
N
H2
When an excess of concentrated NH3(aq) is added to F, the precipitate dissolves to

form a deep blue solution.
(ii) State the formula of the ion responsible for the deep blue colour.
..................................................................................................................................
(iii) What type of reaction is occurring here?
..................................................................................................................................
[3]
[Total: 15]
10 For
Examiner’s
Use
7 The nitration of benzene occurs in the following steps.
H NO2 NO2
+
+ NO2 + + H+
(a) What reagents and conditions are needed for this reaction?
......................................................................................................................................[2]
+
(b) Write an equation showing how the electrophile NO 2 is formed from the reagents.
......................................................................................................................................[1]
(c) The nitration of methylbenzene produces mainly 2-nitromethylbenzene, whereas the

nitration of benzoic acid produces mainly 3-nitrobenzoic acid.
CH3 CO2H
NO2
NO2
2-nitromethylbenzene 3-nitrobenzoic acid
Use this information to suggest suitable intermediates G and H in the following two
2-stage syntheses of chlorobenzoic acids, and suggest suitable reagents for reactions
I to IV.
CO2H
Cl
II
CH3
I
G
III
CO2H
IV
Cl
H
reagents:
reaction I ................................................ reaction II ................................................
reaction III .............................................. reaction IV ...............................................

[4]
[Total: 7]
© UCLES 2007 9701/04/O/N/07
11 For
Examiner’s
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8 (a) DNA carries the genetic code in living organisms and consists of a double helix.
(i) Describe what is meant by a double helix.
..................................................................................................................................
..................................................................................................................................
(ii) How are the strands of the double helix held together?
..................................................................................................................................
..................................................................................................................................
[2]
(b) In replicating the genetic code two RNA molecules, mRNA and tRNA, are used to
perform functions called transcription and translation.
Describe the role of the RNA molecules in these two functions.
transcription .....................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
translation ........................................................................................................................
..........................................................................................................................................
......................................................................................................................................[4]
(c) When an egg is boiled, the protein changes from a viscous liquid to a solid.
(i) Suggest what causes this change as the protein is heated.
..................................................................................................................................
..................................................................................................................................
(ii) Why is there no change to the primary structure of the protein under these
conditions?
..................................................................................................................................
..................................................................................................................................
[2]
12 For
Examiner’s
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(d) Describe in outline how energy is provided in animal cells.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
[Total: 11]
9 (a) Explain with reference to energy states how 1H NMR can supply information about the
structure of molecules.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[3]
(b) Nuclear magnetic resonance is used in magnetic resonance imaging scanners. These
scanners are increasingly used in hospitals to detect tumours. Suggest why magnetic
resonance techniques are better than X-rays.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
......................................................................................................................................[2]
© UCLES 2007 9701/04/O/N/07
13 For
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(c) The NMR spectrum shown below was obtained from a simple organic molecule,
G, CxHyO2. When a sample of G was placed in a mass spectrometer, the ratio of the
M : M+1 peaks for the molecule was 14.5 : 0.66.
3
absorbance
11 10 9 8 7 6 5 4 3 2 1 0
chemical shift, ␦
(i) Calculate how many carbon atoms there are in the molecule.
(ii) Use the NMR spectrum and the Data Booklet to work out the structure of G.
[5]
[Total: 10]
14 For
Examiner’s
Use
10 Read the following article about the use of bacteria in mining, and then answer the questions
that follow it.
The discovery that bacteria could ʻmineʼ metals for us was made in Spain. The Rio Tinto mine, in the
southwest corner of Spain, was originally mined for copper by the Romans some 2,000 years ago.
In 1752, some mining engineers looked over the mine to see if it could possibly be re-opened. They
noticed streams of a blue-green liquid running from spoil heaps of the processed rock that lay around
the mine. When this blue-green liquid ran over iron, it coated the iron with a brown film. The brown
film was metallic copper.
There was still some copper left in the spoil heaps. At the time, everybody thought that the copper
was being dissolved in the liquid through a simple chemical reaction. But in 1947, US scientists
discovered that the copper was being ʻminedʼ by a bacterium called Thiobacillus ferrooxidans.
The bacterium Thiobacillus ferrooxidans lives off the chemical energy trapped in metal sulphides.
In the ore, the copper exists as copper sulphide. The bacteria gain energy by converting the copper
sulphide to copper sulphate, which is then excreted. At the same time, they absorb the difference in
energy in the chemical bonds. These bacteria can also obtain energy in similar reactions with ores of
zinc, lead and uranium.
(a) Use the Data Booklet to explain why the blue-green liquid coated the iron with copper.
Write an equation for the reaction.
..........................................................................................................................................
..........................................................................................................................................
[2]
(b) Suggest two reasons why this method of extracting copper might be useful for ore
containing only a small percentage of copper.
(i) .................................................................................................................................
..................................................................................................................................
(ii) .................................................................................................................................
..................................................................................................................................
[2]
(c) Suggest one disadvantage of using bacteria rather than traditional mining and smelting
methods.
..........................................................................................................................................
......................................................................................................................................[1]
© UCLES 2007 9701/04/O/N/07
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(d) In conventional copper mining, the ore will typically contain 0.5 – 2.0% copper, which
gives an idea of what a valuable resource copper is.
(i) The ore from a particular mine contains 0.75% copper, and 150 000 tonnes of ore
are mined each year. From this ore about 60% of the copper is extracted, and the
remainder is left in the ‘spoil heaps’ of processed ore.
What mass of copper is extracted each year?
(ii) If the use of bacteria can recover a further 17% of copper from the spoil heaps,
what is the extra mass of copper produced?
[2]
(e) Suggest why bacteria are unlikely to be used in the extraction of aluminium.
..........................................................................................................................................
......................................................................................................................................[1]
(f) Metals like copper and zinc from abandoned mines can contaminate ground-water.
Suggest one way of removing these contaminants.
..........................................................................................................................................
......................................................................................................................................[1]
[Total: 9]
© UCLES 2007 9701/04/O/N/07
16
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9701/04/O/N/07
*8268374436*
CHEMISTRY 9701/04
1 hour 45 minutes
Do not use staples, paper clips, highlighters, glue or correction fluid
Section A
Section B
appropriate units.
part question. 6
10
Total
SHW 00019 4/07 T63628/1

2 For
Examiner’s
Use
Section A
1 (a) Natural bromine consists of the two isotopes 79Br and 81Br in roughly equal proportions.
The mass spectrum of bromine consists of 5 peaks.
(i) Suggest the mass numbers for the 5 peaks and the identities of the species
responsible for them.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Suggest the ratios of the relative abundances of
• the three lines with the highest mass numbers,
..................................................................................................................................
• the two lines with the lowest mass numbers.
..................................................................................................................................
[4]
Esters of 2,3-dibromopropan-1-ol with phosphoric acid are useful flame retardants used in
plastics and fibres.
2,3-dibromopropan-1-ol can be made from propenal by the following two-stage process.
H
C CH2 CH2OH
I II
CH2 CHO Br CH
propenal Br
2,3-dibromopropan-1-oI
A
© UCLES 2008 9701/04/O/N/08
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(b) (i) Draw the structure of the intermediate A in the box opposite.
• reaction I,
..................................................................................................................................
• reaction II.
..................................................................................................................................
[3]
(c) The mass spectrum of 2,3-dibromopropan-1-ol includes the following peaks.
mass number relative abundance
31 100
106 44
108 45
185 0.3
187 0.6
189 0.3
(i) At what mass number would you expect the molecular ion to occur?
..................................................................................................................................
(ii) Identify the molecular formula (including isotopic composition where relevant) of
these 6 peaks.
mass number molecular formula
31
106
108
185
187
189
[5]
[Total: 12]
4 For
Examiner’s
Use
2 In the late 19th century the two pioneers of the study of reaction kinetics, Vernon Harcourt
and William Esson, studied the rate of the reaction between hydrogen peroxide and iodide
ions in acidic solution.
H2O2 + 2I– + 2H+ 2H2O + I2
This reaction is considered to go by the following steps.
step 1 H2O2 + I– IO– + H2O
step 2 IO– + H+ HOI
step 3 HOI + H+ + I– I2 + H2O
The general form of the rate equation is as follows.
rate = k[H2O2]a[I–]b[H+]c
(a) Suggest how the appearance of the solution might change as the reaction takes place.
.................................................................................................................................... [1]
(b) Suggest values for the orders a, b and c in the rate equation for each of the following
cases.
numerical value
case
a b c
step 1 is the slowest overall
[3]
A study was carried out in which both [H2O2] and [H+] were kept constant at 0.05 mol dm–3,
and [I–] was plotted against time. The following curve was obtained.
0.001
0.0009
0.0008
0.0007
0.0006
[I– ion] / mol dm–3 0.0005
0.0004
0.0003
0.0002
0.0001
0
0 30 60 90 120 150 180 210 240 270 300
time / s
© UCLES 2008 9701/04/O/N/08
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To gain full marks for the following answers you will need to draw relevant construction lines
on the graph opposite to show your working. Draw them using a pencil and ruler.
(c) Calculate the initial rate of this reaction and state its units.
rate = ........................ units ....................... [2]
(d) Use half-life data calculated from the graph to show that the reaction is first order with
respect to [I–].
.................................................................................................................................... [2]
(e) Use the following data to deduce the orders with respect to [H2O2] and [H+], explaining
your reasoning.
[H2O2] / mol dm–3 [H+] / mol dm–3 relative rate
0.05 0.05 1.0
0.07 0.05 1.4
0.09 0.07 1.8
..........................................................................................................................................
..........................................................................................................................................
order with respect to [H2O2] = .....................................................
order with respect to [H+] = .....................................................

[2]
(f) From your results, deduce which of the three steps is the slowest (rate determining)
step.
.................................................................................................................................... [1]
[Total: 11]
6 For
Examiner’s
Use
3 (a) (i) Describe and explain the trend observed in the thermal stability of the carbonates
of the Group II elements.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) By quoting suitable data from the Data Booklet suggest how the thermal stabilities
of
• zinc carbonate and

• lead carbonate
might compare to that of calcium carbonate.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[6]
(b) Malachite is an ore of copper. It contains the following percentages by mass.
copper 57.7%
oxygen 36.2%
carbon 5.4%
hydrogen 0.9%
Malachite reacts with dilute H2SO4 producing a gas B that turns limewater milky and
leaving a blue solution C.
When heated in the absence of air, malachite produces gas B and steam, and leaves a
black solid D. D reacts with dilute H2SO4 to produce the same blue solution C.
Adding iron filings to C produces a pink solid E and a pale green solution F.
(i) Calculate the empirical formula of malachite.
..................................................................................................................................
© UCLES 2008 9701/04/O/N/08
7 For
Examiner’s
Use
(ii) Suggest the formula of the ion responsible for the blue colour of solution C.
..................................................................................................................................
(iii) Identify the black solid D and calculate the mass of D that could be obtained by
heating 10 g of malachite.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iv) Use data from the Data Booklet to identify the pink solid E and the solution F, and
suggest an equation for the reaction producing them.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(v) What type of reaction is the reaction that produces E and F?
..................................................................................................................................
(vi) Describe and explain what you would see happen when dilute NH3(aq) is added
slowly to the solution C until it is in an excess.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[13]
[Total: 19]
8 For
Examiner’s
Use
4 (a) The viscosity of engine oil can be improved by the addition of certain medium chain-
length polymers.
A portion of the chain of one such polymer is shown below.
–CH2CH(CH2CH2CH3)CH2CH(CH2CH2CH3)CH2–
On average, the molecules of the medium-chain polymer contain 40 carbon atoms.
(i) Suggest the structure of the monomer.
..................................................................................................................................
(ii) How many monomer units are incorporated into the average molecule of the
polymer?
..................................................................................................................................
[2]
(b) Used car engine oil can be recycled for use as a fuel by the processes of distillation and
cracking.
(i) Assuming a typical molecule of engine oil has the formula C40H82, suggest an
equation for a cracking reaction that could produce diesel fuel with the formula
C16H34 and other hydrocarbons only.
..................................................................................................................................
(ii) What conditions are needed for this cracking reaction?
..................................................................................................................................
(iii) Considering only the bonds broken and the bonds formed during the reaction, use
the Data Booklet to calculate the enthalpy change for the reaction you wrote in
(b)(i).
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iv) Comment on how the conditions you described in (b)(ii) relate to the enthalpy
change you calculated in (b)(iii).
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 6]
© UCLES 2008 9701/04/O/N/08
9 For
Examiner’s
Use
5 (4-aminophenyl)ethanoic acid (4-APEA) and its derivatives are being investigated as possible
drugs to treat chronic inflammation of the intestines.
The synthesis of 4-APEA from methylbenzene is shown in the following scheme.
CH3 CH2Cl
I II
HNO3 + H2SO4
NO2
G
III
CH2CO2H CH2CN
V IV
H3O+
NH2 NO2
4-APEA H
(a) Draw the structures of the compounds G and H in the boxes above. [2]
(b) Suggest reagents and conditions for the following steps.
• step II
..........................................................................................................................................
• step III
..........................................................................................................................................
• step V
..........................................................................................................................................
[3]
[Total: 5]
10 For
Examiner’s
Use
6 Suggest a test or simple reaction you could carry out on each of the following pairs of
compounds to enable them to be distinguished.
(a) CH3COCH2CH2CH3 CH3CH2COCH2CH3
J K
(i) description of test or reaction
..................................................................................................................................
..................................................................................................................................
(ii) observation with compound J
..................................................................................................................................
(iii) observation with compound K
..................................................................................................................................
[2]
(b)
NH2 NH2
L M
..................................................................................................................................
..................................................................................................................................
(ii) observation with compound L
..................................................................................................................................
(iii) observation with compound M
..................................................................................................................................
[2]
© UCLES 2008 9701/04/O/N/08
11 For
Examiner’s
Use
(c) CH3CH2COCl CH3CH2CH2Cl
N P
..................................................................................................................................
..................................................................................................................................
(ii) observation with compound N
..................................................................................................................................
(iii) observation with compound P
..................................................................................................................................
[2]
(d) CH3CH2CONH2 CH3CH2CH2NH2
Q R
..................................................................................................................................
..................................................................................................................................
(ii) observation with compound Q
..................................................................................................................................
(iii) observation with compound R
..................................................................................................................................
[2]
[Total: 8]
12 For
Examiner’s
Use
7 (a) Explain briefly what is meant by the word protein.
..........................................................................................................................................
.................................................................................................................................... [1]
(b) Describe how peptide bonds are formed between amino acids during the formation of a
tripeptide. Include diagrams and displayed formulae in your answer.
.................................................................................................................................... [3]
(c) Describe how proteins can be broken down into amino acids in the laboratory without
the aid of enzymes.
.................................................................................................................................... [2]
(d) When a small polypeptide S was broken down in this way, three different amino acids
were produced according to the following reaction.
S 3 NH2CH2CO2H + 2 NH2CHCO2H + 2 NH2CHCO2H
CH3 CH2
Mr = 75 Mr = 89
Mr = 165
(i) How many peptide bonds were broken during this reaction?
..................................................................................................................................
(ii) Calculate the Mr of the polypeptide S.
Mr = .....................................................
[3]
[Total: 9]
© UCLES 2008 9701/04/O/N/08
13
BLANK PAGE
14 For
Examiner’s
Use
8 (a) Enzymes play a vital role in all living organisms, helping chemical reactions to take
place at body temperature.
(i) The diagram below shows the reaction pathway of an enzyme-catalysed reaction
without an enzyme present. On the diagram sketch the pathway if the enzyme was
present.
energy
reactants
products
reaction pathway
(ii) What type of molecule are most enzymes?
..................................................................................................................................
(iii) Why do many enzymes lose their catalytic effectiveness above 40 °C?
..................................................................................................................................
[3]
(b) (i) Explain the difference between competitive and non-competitive inhibition of an
enzyme.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
© UCLES 2008 9701/04/O/N/08
15 For
Examiner’s
Use
(ii) The graph below shows how the rate of an enzyme-catalysed reaction varies with
substrate concentration in the absence of an inhibitor.
For a given amount of enzyme, Vmax represents the rate when all of the active sites
on the enzyme are being used.
Vmax
reaction rate
substrate concentration
Sketch on the diagram curves to show the effect on the rate of reaction of:
I a competitive inhibitor;
II a non-competitive inhibitor.
Clearly label your curves.

[4]
(c) Heavy metal ions like Hg2+ can bind irreversibly to enzymes and this can result in
poisoning.
(i) Suggest to what atom or group Hg2+ ions bind.
..................................................................................................................................
(ii) Explain how this affects enzyme activity.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 10]
16 For
Examiner’s
Use
9 The technology of DNA fingerprinting has enormously advanced scientific identification
techniques in medicine, crime detection and archaeology in recent years.
(a) (i) In order to prepare a DNA sample for analysis, the DNA is treated with restriction
enzymes. What do restriction enzymes do?
..................................................................................................................................
..................................................................................................................................
(ii) What is the next stage in DNA analysis, after the treatment with restriction
enzymes?
..................................................................................................................................
(iii) How are the DNA fragments made visible?
..................................................................................................................................
[3]
(b) NMR and X-ray crystallography have made significant contributions to our knowledge of
the structure of proteins and, in the pharmaceutical industry, how drugs react with target
proteins.
(i) Suggest an advantage of each technique in helping to determine protein structure.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) MRI scanning is a medical technique based on NMR spectroscopy. It is particularly

useful for looking for tumours in healthy tissue.
Suggest how this technique can distinguish tumour tissue from healthy tissue.
..................................................................................................................................
..................................................................................................................................
[3]
© UCLES 2008 9701/04/O/N/08
17 For
Examiner’s
Use
(c) A saturated molecule of formula CxHyNO was subjected to analysis by mass spectrometry
and NMR spectroscopy. In the mass spectrum of the compound, the M peak was at
m/e 73 and the ratio of the heights of the M:M+1 peak was 48 : 1.7.
(i) Using the data from the mass spectrum, determine the values of x and y in the
formula of the compound.
(ii) Use the data from (i) together with the NMR spectrum below to deduce a structure
for the compound, explaining how you arrive at your answer.
11 10 9 8 7 6 5 4 3 2 1 0
chemical shift, / ppm
[4]
[Total: 10]
18 For
Examiner’s
Use
10 (a) Silk from silkworms, used as a fabric shows a different secondary structure to that
produced by spiders.
less ordered
sheets
glycine rich strand

silkworm silk highly ordered spider dragline silk
sheets
(i) What sort of bonding would you expect to occur between adjacent parts of the
protein chains in each form of silk?
silkworm ...................................................................................................................
spider .......................................................................................................................
(ii) Suggest two differences in properties that these forms of silk could have. Explain
your answer.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) Spider dragline silk contains large amounts of the amino acid glycine. How does
this affect the properties of the silk?
..................................................................................................................................
..................................................................................................................................
[5]
© UCLES 2008 9701/04/O/N/08
19 For
Examiner’s
Use
(b) Both forms of silk are condensation polymers.
(i) Explain what is meant by a condensation polymer.
..................................................................................................................................
..................................................................................................................................
(ii) Another type of polymer is called an addition polymer. Name an example of an

addition polymer.
............................................................
(iii) Suggest why condensation polymers such as proteins show a wider range of
properties than addition polymers.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[5]
[Total: 10]
© UCLES 2008 9701/04/O/N/08
20
BLANK PAGE
9701/04/O/N/08
*5640244407*
CHEMISTRY 9701/41
1 hour 45 minutes

1
Section B
4
part question. 5
Total
DC (FF/DT) 12823/4
2
Section A For
Examiner’s
1 (a) The Group IV oxides CO2 and SiO2 differ widely in their physical properties. Describe
these differences and explain them in terms of their structure and bonding.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
(b) What are the properties of a ceramic material? Why is silicon(IV) oxide very suitable as
a component of ceramics?
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(c) Lead(II) oxide reacts with both acids and bases.
(i) What is the name given to oxides that have this property?
..................................................................................................................................
(ii) Write a balanced equation for the reaction between PbO and NaOH.
..................................................................................................................................
[2]
© UCLES 2009 9701/41/O/N/09
3
(d) Tin forms an oxide, A, that contains the metal in both oxidation states II and IV. The For
formula of A can be found by the following method. Examiner’s
Use
• A sample of A was dissolved in H2SO4(aq), producing solution B, which was a mixture

of tin(II) sulfate and tin(IV) sulfate.
• A 25.0 cm3 sample of solution B was titrated with 0.0200 mol dm–3 KMnO4.
13.5 cm3 of KMnO4 was required to reach the end-point.
• Another 25.0 cm3 sample of solution B was stirred with an excess of powdered
zinc. This converted all the tin into tin(II). The excess of zinc powder was filtered off
and the filtrate was titrated with 0.0200 mol dm-3 KMnO4, as before.
This time 20.3 cm3 of KMnO4 was required to reach the end-point.
The equation for the reaction occurring during the titration is as follows.
2MnO4– + 16H+ + 5Sn2+ 2Mn2+ + 8H2O + 5Sn4+
(i) Write a balanced equation for the reaction between Zn and Sn4+.
..................................................................................................................................
(ii) Use the Data Booklet to calculate the E o- values for the reactions between
• Zn and Sn4+, ....................................................................................................
• MnO4– and Sn2+.. ................................................................................................
(iii) Use the results of the two titrations to calculate
• the number of moles of Sn2+ in the first titration sample,
..................................................................................................................................
..................................................................................................................................
• the number of moles of Sn2+ in the second titration sample.
..................................................................................................................................
..................................................................................................................................
(iv) Use the results of your calculation in (iii) to deduce the Sn2+/ Sn4+ ratio in the oxide
A, and hence suggest the formula of A.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[8]
4
(e) A major use of tin is to make ‘tin plate’, which is composed of thin sheets of mild steel For
electroplated with tin, for use in the manufacture of food and drinks cans. A tin coating of Examiner’s
1.0 3 10–5 m thickness is often used. Use
(i) Calculate the volume of tin needed to coat a sheet of steel 1.0 m 3 1.0 m to this
thickness, on one side only.
..................................................................................................................................
..................................................................................................................................
(ii) Calculate the number of moles of tin that this volume represents.
[The density of tin is 7.3 g cm–3.]
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) The solution used for electroplating contains Sn2+ ions. Calculate the quantity of
electricity in coulombs needed to deposit the amount of tin you calculated in (ii).
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 19]
© UCLES 2009 9701/41/O/N/09
5
BLANK PAGE
6
2 Calcium chloride, CaCl2, is an important industrial chemical used in refrigeration plants, for For
de-icing roads and for giving greater strength to concrete. Examiner’s
Use
(a) Show by means of an equation what is meant by the lattice energy of calcium chloride.
..................................................................................................................................... [1]
(b) Suggest, with an explanation, how the lattice energies of the following salts might
compare in magnitude with that of calcium chloride.
(i) calcium fluoride, CaF2
..................................................................................................................................
..................................................................................................................................
(ii) calcium sulfide, CaS
..................................................................................................................................
..................................................................................................................................
[3]
(c) Use the following data, together with additional data from the Data Booklet, to calculate
the lattice energy of CaCl2.
standard enthalpy change of formation of CaCl2 –796 kJ mol–1
standard enthalpy change of atomisation of Ca(s) +178 kJ mol–1
electron affinity per mole of chlorine atoms –349 kJ mol–1
enthalpy
Ca(s) + Cl 2(g)
lattice energy = ............................................ kJ mol–1 [3]
© UCLES 2009 9701/41/O/N/09
7
(d) When a solution of CaCl2 is added to a solution of the dicarboxylic acid, malonic acid, For
the salt calcium malonate is precipitated as a white solid. The solid has the following Examiner’s
composition by mass: Ca, 28.2 %; C, 25.2 %; H, 1.4 %; O, 45.2 %. Use
(i) Calculate the empirical formula of calcium malonate from these data.
(ii) Suggest the structural formula of malonic acid.
[3]
[Total: 10]
8
3 One major difference between the properties of compounds of the transition elements and For
those of other compounds is that the compounds of the transition elements are often Examiner’s
coloured. Use
(a) Explain in detail why many transition element compounds are coloured.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [3]
(b) The following graph shows the absorption spectrum of two complexes containing copper.
blue green yellow red infra-red
[Cu(NH3)4(H2O)2]2+
absorbance
[Cu(H2O)6]2+
400 500 600 700 800 900 1000

wavelength / nm
(i) State the colours of the following complex ions.
[Cu(H2O)6]2+ .................................................................................................
[Cu(NH3)4(H2O)2]2+ .................................................................................................
(ii) Using the spectra above give two reasons why the colour of the [Cu(NH3)4(H2O)2]2+
ion is deeper (more intense) than that of the [Cu(H2O)6]2+ ion.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) Predict the absorption spectrum of the complex [Cu(NH3)2(H2O)4]2+, and sketch
this spectrum on the above graph. [6]
© UCLES 2009 9701/41/O/N/09
9
(c) Copper forms a complex with chlorine according to the following equilibrium. For
Examiner’s
Cu2+(aq) + 4Cl –(aq) [CuCl4]2–(aq) Use
(i) Write an expression for the equilibrium constant, Kc , for this reaction, stating its
units.
Kc = units
...................................................... ......................................................
(ii) The numerical value of Kc is 4.2 3 105.

Calculate the [[CuCl4] 2–] / [Cu2+ ] ratio when [Cl – ] = 0.20 mol dm–3.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 12]
10
4 Cyclohexanol and phenol are both solids with low melting points that are fairly soluble in For
water. Examiner’s
Use
OH OH
cyclohexanol phenol
(a) Explain why these compounds are more soluble in water than their parent hydrocarbons
cyclohexane and benzene.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(b) Explain why phenol is more acidic than cyclohexanol.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
© UCLES 2009 9701/41/O/N/09
11
(c) For each of the following reagents, draw the structural formula of the product obtained For
for each of the two compounds. If no reaction occurs write no reaction in the box. Examiner’s
Use
reagent product with cyclohexanol product with phenol
Na(s)
NaOH(aq)
Br2(aq)
I2(aq) + OH–(aq)
an excess of
acidified Cr2O 27 –(aq)
[7]
(d) Choose one of the above five reagents that could be used to distinguish between
cyclohexanol and phenol. Describe the observations you would make with each compound.
reagent ........................................................................................
observation with cyclohexanol ........................................................................................
observation with phenol ........................................................................................

[2]
[Total: 13]
12
5 Kevlar is a tough polyamide used in bullet-proof vests and high-specification bicycle tyres. For
It can be manufactured by the following process. Examiner’s
Use
I II
H 3C CH3 HO2C CO2H ClOC COCl H 2N NH2
C D
Kevlar
(a) (i) Suggest reagents and conditions for
reaction I, .............................................................................................................
reaction II. .............................................................................................................
(ii) Draw the structural formula of one repeat unit of Kevlar in the box above.
[4]
(b) The di-acid chloride C reacts with a variety of reagents. Suggest the structural formulae
of the products of the reaction of C with
(i) CH3NH2,
(ii) HOCH2CH2OH.
[3]
© UCLES 2009 9701/41/O/N/09
13
(c) The diamine D also reacts with a variety of reagents. Suggest the structural formulae of For
the products of the reaction of D with Examiner’s
Use
(i) HCl (aq),
(ii) Br2(aq).
[3]
(d) 4-aminobenzoic acid, E, is a useful intermediate for making dyes.
III + IV
HO2C NH2 HO2C N N HO2C N=N OH
Cl -
E a dye
Suggest reagents and conditions for
reaction III, .....................................................................................................................
reaction IV. .....................................................................................................................

[4]
(e) 4-aminobenzoic acid, E, forms a zwitterion.
(i) What is meant by the term zwitterion?
..................................................................................................................................
..................................................................................................................................
(ii) Draw the structural formula of the zwitterion formed from 4-aminobenzoic acid.
[2]
[Total: 16]
14
Section B For
Examiner’s
Use
6 (a) The diagram shows part of one strand of DNA. Draw the complementary strand, labelling
the bonds formed to the original strand, and labelling the components of the strand you
draw.
sugar sugar sugar

phosphate phosphate phosphate
T A C
[3]
(b) Briefly describe the roles of each of the following in protein synthesis.
(i) tRNA .........................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) the ribosome ............................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
© UCLES 2009 9701/41/O/N/09
15
(c) Some diseases, such as sickle cell anaemia, are caused by a single mutation in the For
DNA for a particular gene. This causes the haemoglobin produced to change the shape Examiner’s
of red blood cells, reducing their efficiency in carrying oxygen. Use
(i) What is meant by a mutation?
..................................................................................................................................
(ii) Explain why such a mutation could alter the bonding in haemoglobin.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 11]
16
7 This question is about the modern techniques of analysis which may be used to determine For
molecular structures. Examiner’s
Use
(a) In X-ray crystallography X-rays are diffracted by the electron clouds surrounding
individual atoms in the structure.
(i) What useful information is provided by X-ray crystallography?
..................................................................................................................................
..................................................................................................................................
(ii) Why cannot hydrogen atoms in a structure be detected by this technique?
..................................................................................................................................
[2]
(b) Suggest how structures of complex molecules such as enzymes, derived from X-ray
crystallography, can help explain their biochemical behaviour.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
(c) NMR spectroscopy, in contrast to X-ray crystallography, is frequently used to examine

protons in organic molecules.
(i) What feature of protons enables their detection by NMR spectroscopy?
..................................................................................................................................
© UCLES 2009 9701/41/O/N/09
17
(ii) The NMR spectrum below was obtained from a compound X, CxHyOz. In the mass For
spectrum of the compound, the M : M+1 ratio was found to be 25:2. Examiner’s
Use
Determine the values of x, y and z in the formula of X and deduce a possible

structure for the compound, explaining how you arrive at your conclusion.
11 10 9 8 7 6 5 4 3 2 1 0
δ/ppm
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
Possible structure of X
[6]
[Total:10]
18
8 A new method of making very light, flexible batteries using nanotechnology was announced For
in August 2007. Read the passage and answer the questions related to it. Examiner’s
Use
Researchers have developed a new energy-storage device that could easily be mistaken
for a simple sheet of black paper. The nano-engineered battery is lightweight, ultra-thin and
completely flexible. It is geared towards meeting the difficult design and energy requirements
of tomorrow’s gadgets, such as implantable medical devices and even vehicles.
Researchers soaked ‘paper’ in an ionic liquid electrolyte which carries the charge. They then
treated it with aligned carbon nanotubes, which give the device its black colour.
The nanotubes act as electrodes and allow the storage devices to conduct electricity. The
device, engineered to function as both a battery and a supercapacitor, can provide the long,
steady power output comparable to a conventional battery, as well as a supercapacitor’s
quick burst of high energy. The device can be rolled, twisted, folded, or cut into shapes with
no loss of strength or efficiency. The ‘paper’ batteries can also be stacked, like a pile of
printer paper, to boost the total power output.
1. Conventional batteries produce electrons through a chemical reaction between electrolyte

and metal.
2. Chemical reaction in the ‘paper’ battery is between electrolyte and carbon nanotubes.
3. Electrons collect on the negative terminal of a battery.
4. Electrons must flow from the negative terminal, through the external circuit to the positive
terminal for the chemical reaction to continue.
nanotube
© UCLES 2009 9701/41/O/N/09
19
(a) From your knowledge of the different structures of carbon, suggest which of these is For
used to make nanotubes. Examiner’s
Use
..................................................................................................................................... [1]
(b) Suggest a property of this structure that makes it suitable for making nanotubes.
..........................................................................................................................................
..................................................................................................................................... [1]
(c) Carbon in its bulk form is brittle like most non-metallic solids. Suggest why the energy
storage device described can be rolled into a cylinder.
..........................................................................................................................................
..................................................................................................................................... [1]
(d) Name an example of an ‘ionic liquid electrolyte’ (not a solution).
..................................................................................................................................... [1]
[Total: 4]
20
9 In recent years a great deal of research has been carried out into finding different anti-cancer For
drugs. Tumours, which are often symptoms of cancer, are produced when cells replicate Examiner’s
uncontrollably. This in turn is brought about by the replication of DNA in these cells. Use
Two anti-cancer agents are mechlorethamine and cis-platin. They work by binding to the
DNA and preventing replication.
DNA
Cl
DNA
G
CH3 N CH3 N
G
NH3 Cl NH3 G C
Cl Pt Pt
NH3 Cl NH3 G C
mechlorethamine crosslinked DNA cis-platin
(a) (i) What type of bonding attaches both anti-cancer agents to the DNA?
..................................................................................................................................
(ii) Suggest how each of the anti-cancer agents prevents replication of the DNA.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[5]
[Total: 5]
© UCLES 2009 9701/41/O/N/09
*7729777231*
CHEMISTRY 9701/42
1 hour 45 minutes

1
Section B
4
part question. 5
Total
DC (AT/CG) 14049/2
2
Section A For
Examiner’s
1 (a) Describe and explain qualitatively the trend in the solubilities of the sulfates of the
Group II elements.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
(b) The major ore of barium is barytes, BaSO4. This is very unreactive, and so other barium
compounds are usually made from the sulfide, BaS. This is obtained by heating the
crushed ore with carbon, and extracting the BaS with water.
BaSO4(s) + 4C(s) BaS(s) + 4CO(g)
When 250 g of ore was heated in the absence of air with an excess of carbon, it was
found that the CO produced took up a volume of 140 dm3 at 450 K and 1 atm.
(i) Calculate the number of moles of CO produced.
..................................................................................................................................
(ii) Calculate the number of moles of BaSO4 in the 250 g sample of the ore.
..................................................................................................................................
(iii) Calculate the percentage by mass of BaSO4 in the ore.
..................................................................................................................................
[4]
© UCLES 2009 9701/42/O/N/09
3
(c) (i) Use the following data and data from the Data Booklet to construct a Born-Haber For
cycle and calculate the lattice energy of BaS. Examiner’s
Use
standard enthalpy change of formation of BaS(s) –460 kJ mol–1
standard enthalpy change of atomisation of Ba(s) +180 kJ mol–1
standard enthalpy change of atomisation of S(s) +279 kJ mol–1
electron affinity of the sulfur atom –200 kJ mol–1
electron affinity of the S– ion +640 kJ mol–1
lattice energy = ............................. kJ mol–1
(ii) Explain whether the magnitude of the lattice energy of BaS is likely to be greater or
less than that of BaO.
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 11]
4
2 (a) Describe and explain how the basicities of ammonia, ethylamine and phenylamine For
differ. Examiner’s
Use
NH2
NH3 CH3CH2NH2
ammonia ethylamine phenylamine
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
(b) Describe how the use of aqueous silver nitrate and aqueous ammonia can distinguish
between aqueous solutions containing chloride, bromide or iodide ions by filling in the
following table.
halide observation when observation when observation when

AgNO3(aq) is added dilute NH3(aq) is concentrated NH3(aq)
added is added
chloride
bromide
iodide
[3]
(c) Silver bromide is sparingly soluble in water.
AgBr(s) Ag+(aq) + Br–(aq) Ksp = 5 × 10–13 mol2 dm–6
(i) Calculate [Ag+(aq)] in a saturated aqueous solution of AgBr.
[Ag+(aq)] = .......................... mol dm–3
(ii) State and explain whether AgBr will be less or more soluble in 0.1 mol dm–3 KBr
than it is in pure water.
..................................................................................................................................
..................................................................................................................................
[2]
© UCLES 2009 9701/42/O/N/09
5
(d) Silver ions form complexes with ammonia and with amines. For
Examiner’s
Ag+(aq) + 2RNH2(aq) [Ag(RNH2)2]+(aq) Use
(i) Write an expression for the Kc for this reaction, and state its units.
Kc = units
...................................................... ......................................................
Kc has the numerical value of 1.7 × 107 when R = H.
(ii) Using your expression for Kc calculate the [NH3(aq)] needed to change the [Ag+(aq)]
in a 0.10 mol dm–3 solution of silver nitrate to the value that you calculated in (c)(i).
[NH3(aq)] = .......................... mol dm–3
(iii) Explain whether you would expect the Kc for the reaction where R = C2H5 to be
greater or less than that for the reaction where R = H.
..................................................................................................................................
..................................................................................................................................
[5]
[Total: 13]
6
3 Iron metal and its compounds are useful catalysts in certain reactions. For
Examiner’s
(a) Apart from its catalytic activity, state two properties of iron or its compounds that Use
show that it is a transition element.
..........................................................................................................................................
...................................................................................................................................... [2]
(b) You are provided with a solution of KMnO4 of known concentration in a burette.
Outline how you could use this solution to find out the concentration of Fe2+(aq) in a
solution. You should include relevant equations for any reactions you describe.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [4]
(c) For each of the following equations, write the oxidation number of the element printed
in bold underneath its symbol, and balance the equation by adding appropriate numbers
before each species.
(i) ........ MnO –4 + ........ SO2 + ........ H2O → ........ Mn2+ + ........ SO24– + ........ H+
oxidation numbers: ........ ........ ........ ........
(ii) ........ Cr2O27– + ........ NO2 + ........ H+ → ........ Cr3+ + ........ NO–3 + ........ H2O
oxidation numbers: ........ ........ ........ ........

[6]
© UCLES 2009 9701/42/O/N/09
7
(d) Outline the role that Fe3+ ions play in catalysing the reaction between iodide ions and For
peroxydisulfate(VI) ions. Examiner’s
Use
2I– + S2O28– I2 + 2SO24–
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
[Total: 14]
8
4 (a) What is meant by the term bond energy? For

Examiner’s
.......................................................................................................................................... Use
...................................................................................................................................... [2]
(b) Describe and explain what is observed when a red-hot wire is plunged into separate
samples of the gaseous hydrogen halides HCl and H I.
How are bond energy values useful in interpreting these observations?
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
(c) The following reaction occurs in the gas phase.
3F2(g) + Cl2(g) 2ClF3(g), ∆H—

o = –328 kJ mol–1
r
Use these and other data from the Data Booklet to calculate the average bond energy
of the Cl-F bond in Cl F3. [2]
[Total: 7]
© UCLES 2009 9701/42/O/N/09
9
BLANK PAGE
10
5 (a) All the carbon atoms in benzene lie in the same plane. This means that they are coplanar, For
but this is not the case with cyclohexane. Examiner’s
Use
benzene cyclohexane
By rotating the molecule around its several C–C bonds, all the carbon atoms in butane
can be made to lie in the same plane, but this is not the case with methylpropane.
H3C H
H3C CH2
CH2 CH3 H3C CH3
butane methylpropane
By considering the 3-dimensional geometry of the following five molecules, and allowing
rotations around C–C bonds, decide whether or not the carbon atoms in each molecule
can be arranged in a coplanar fashion. Then place a tick in the appropriate column in
the table below.
H3C O CH3
C C
H3C CH3
O
A B C
H2N NO2
C C
CH3CH(OH)CO2H CH3
O H
D E
all carbon atoms not all carbon atoms

compound
can be coplanar can be coplanar
A
E
[3]
© UCLES 2009 9701/42/O/N/09
11
(b) Methylbenzene can react with chlorine under different conditions to give the monochloro For
derivatives F and G. Examiner’s
Use
CH3 CH3 CH2Cl

I II
Cl
F G
Suggest reagents and conditions for each reaction.
reaction I
..........................................................................................................................................
reaction II
...................................................................................................................................... [2]
12
(c) Benzyl benzoate is a constituent of many perfumery products, and has also been For
used in the treatment of the skin condition known as scabies. It can be made from Examiner’s
methylbenzene by the following route, which uses one of the chlorination reactions Use
from (b).
CH3
IV
H
III
CO2H CH2OH
VI
O
C CH2
O
benzyl benzoate
(i) Draw the structural formula of the intermediate H in the box above.
© UCLES 2009 9701/42/O/N/09
13
(ii) Suggest reagents and conditions for each reaction. For

Examiner’s
reaction Ill Use
..................................................................................................................................
reaction V
..................................................................................................................................
reaction VI
..................................................................................................................................
(iii) State the type of reaction occurring during
reaction Ill,
..................................................................................................................................
reaction V.
..................................................................................................................................
[6]
[Total: 11]
14
6 Compounds J and K are isomers with the molecular formula C5H11NO, and they contain the For
same functional group. Examiner’s
Use
They may both be obtained from ethanol by the following routes.
CH3CH2OH
HBr + heat K2Cr2O7 + H2SO4 + heat
L M
NH3(excess) I II
CH3CH2CN
III IV
N (C2H7N) CH3COCl
Q P
V
CH3CH2COCl
VI VII
J K
(a) Draw the structural formulae of the lettered compounds J to Q in the boxes above. [7]
© UCLES 2009 9701/42/O/N/09
15
(b) Suggest reagents and conditions for the following. For

Examiner’s
reaction I Use
..........................................................................................................................................
reaction Il
..........................................................................................................................................
reaction IV
...................................................................................................................................... [3]
(c) What type of reaction is occurring in
reaction IV,
..........................................................................................................................................
reaction VI?
...................................................................................................................................... [2]
(d) (i) Name the functional group that is common to compounds J and K.
..................................................................................................................................
(ii) Name the functional group that is common to compounds N and P.
.............................................................................................................................. [2]
[Total: 14]
16
Section B For
Examiner’s
Use
7 (a) Explain, using diagrams where appropriate, the types of interaction responsible for the
primary, secondary and tertiary structure of a protein.
primary structure
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
secondary structure
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
tertiary structure
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [6]
© UCLES 2009 9701/42/O/N/09
17
(b) Enzymes are particular types of protein molecule. Explain briefly how enzymes are able For
to help to break down molecules in the body. Examiner’s
Use
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(c) The graph below shows the effect of inhibition on an enzyme-catalysed reaction.
reaction
rate V
Vmax
substrate concentration [S]
State the type of inhibition shown, giving a reason to support your answer.
type of inhibition ...............................................................................................................
reason ..............................................................................................................................
...................................................................................................................................... [2]
[Total: 10]
18
8 The residues from organohalogen pesticides are known to be a major cause of the decline For
in numbers of different birds of prey in many countries. These residues are concentrated in Examiner’s
birds at the top of food chains. Use
(a) Analysis of the bodies of birds of prey show that the pesticide residues accumulate in
the fatty tissues of the birds. This is because of the high partition coefficient between the
fat in the tissues and water found in blood.
Explain what is meant by the term partition coefficient.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) A particular pesticide has a partition coefficient of 8.0 between the solvent hexane and
water. If a 25 cm3 sample of water containing 0.0050 g of the pesticide is shaken with
a 25 cm3 sample of hexane, calculate the mass of pesticide that will dissolve in the
hexane layer.
[2]
(c) Compounds used as pesticides may contain bromine or chlorine.
(i) What would be the difference in the ratio of the M: M+2 peaks if the pesticide
contained one chlorine rather than one bromine atom?
..................................................................................................................................
(ii) If a given pesticide contains two chlorine atoms per molecule, deduce the relative
heights of the M, M+2 and M+4 peaks.
[3]
© UCLES 2009 9701/42/O/N/09
19
(d) The following graph shows the occurrence of pesticide residues in the eggs of fish-eating For
birds of prey upstream and downstream of a paper mill at Castlegar on the Columbia Examiner’s
River in Canada. Use
Columbia River Basin
120
100
TEQs parts per trillion
80 PCBs
Other Dioxins / Furans
60 Dioxin 2378TCDD
Furan 2378TCDF
40
20
1993
1994
1995
1996
1997
1993
1994
1995
1996
1997
upstream of Castlegar downstream of Castlegar
PCBs, the dioxin 2378TCDD, and the furan 2378TCDF all come from chemicals
containing chlorine.
(i) Suggest which compounds are present directly as a result of the paper mill.
..................................................................................................................................
(ii) By studying the data for 1994, suggest which chemical(s) come from sources other
than the paper mill.
..................................................................................................................................
(iii) Compare the downstream data for 1994 with that for 1997. Suggest what might be
responsible for the change.
..................................................................................................................................
(iv) A molecule of 2378TCDD contains four chlorine atoms. How many molecular ion
peaks would this compound show in its mass spectrum?
..................................................................................................................................
[4]
[Total:11]
20
9 (a) Put the following items in order of increasing size. Use the number 1 to indicate the For
smallest and 3 to indicate the largest. Examiner’s
Use
length of DNA nanosphere diameter cell diameter

molecule in a chromosome
[2]
(b) Nanotechnology has an increasing range of uses across a number of fields including
sport. For example, golf clubs are now being made using nanomaterials.
cross-section of normal cross-section of golf club

golf club shaft shaft with nanomaterial fill
Use the diagrams above and your knowledge of nanomaterials to suggest two properties
of the new shafts. Explain your answers.
(i) ..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) ..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[2]
© UCLES 2009 9701/42/O/N/09
21
(c) A mixture of nano-sized particles of tungsten and vanadium(IV) oxide can be applied For
to the surface of windows and reflects heat whilst letting all light in the visible range Examiner’s
through. Use
Suggest how this variable reflective property is possible using nano-sized particles.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(d) Although silver is well-known as a precious metal, its medicinal properties have been
used for hundreds of years. In ancient Greece silver was used to purify water and until
the development of antibiotics, silver was important in the treatment of large wounds.
(i) What property of silver makes it useful for jewellery?
..................................................................................................................................
(ii) Suggest the property of silver that makes it useful in the treatment of large
wounds.
..................................................................................................................................
(iii) Suggest why nano-sized silver particles are more useful in treating wounds.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 9]
© UCLES 2009 9701/42/O/N/09
22
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9701/42/O/N/09
23
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9701/42/O/N/09
24
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9701/42/O/N/09

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CAMBRIDGE INTERNATIONAL EXAMINATIONS

Candidates answer on the question paper.

INFORMATION FOR CANDIDATES

FOR EXAMINER’S USE

This question paper consists of 11 printed pages and 1 blank page.

1 (a) Write an expression for Kw.

pH at which colour place one tick only

methyl orange 3.1 - 4.4

bromothymol blue 6.0 - 7.6

phenolphthalein 8.3 - 10.0

9701/4/S02 [Turn over

initial rate of run A ....................................................................................................

9701/4/S02 [Turn over

1s2 2s2 2p6 3s2 3p6 .................................................................................................... [1]

9701/4/S02 [Turn over

(a) Name the two functional groups in the paracetamol molecule

.............................................................. and ........................................................... [2]

(ii) NaOH(aq) in the cold,

(iii) NaOH(aq) under reflux.

(c) Paracetamol can be synthesised by reacting 4-aminophenol with compound X.

(i) Suggest a possible identity of X.

CH3 CH3 CH2Cl

(a) State the condition needed for

9701/4/S02 [Turn over

reagent + conditions for step I .........................................................................................

reagent + conditions for step II ........................................................................................

(b) Phenylamine is a weak base.

CAMBRIDGE INTERNATIONAL EXAMINATIONS

READ THESE INSTRUCTIONS FIRST

Answer all questions.

For Examiner’s Use

Stick your personal label here, if 6

This document consists of 12 printed pages.

1 (a) What do you understand by the term standard electrode potential?

direction of electron flow

M 2+(1 mol dm–3) CuSO4(1 mol dm–3)

I A rod of metal M is dipped into a solution of 1 mol dm–3 CuSO4.

9701/04/M/J/03 [Turn over

(b) A useful commercial source of magnesium is sea water, where [Mg2+(aq)] is

Mg2+(aq) + Ca(OH)2(s) → Ca2+(aq) + Mg(OH)2(s)

MgCl2(s) → Mg2+(aq) + 2Cl –(aq)

MgCl2 (s) –641

Explain qualitatively the variation in solubility of the sulphates of the elements in

9701/04/M/J/03 [Turn over

9701/04/M/J/03 [Turn over

(a) Suggest reagents and conditions for step I.

(f) Residues of CN can be destroyed by hydrolysis with an aqueous alkali.

COCH2Cl + OH– COCH2OH + Cl–

Compounds G and H are isomers of compound D.

(ii) Explain the reasoning behind your choice.

9701/04/M/J/03 [Turn over

step III NH3

(i) Suggest a reagent for step I.

When the diacyl chloride of L is reacted with HOCH2CH2OH, a polymer is formed.

(i) What type of polymerisation is occurring here?

(c) The following formula represents a section of another polymer.

(i) What type of polymer is this?

9701/04/M/J/03 [Turn over

(i) Write out the electronic configuration of the titanium atom.

UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS