2.

Factors that affect the rate of a chemical reaction include particle size, concentration of reactants
and the temperature of the reaction.
(i)

Define the term rate of a chemical reaction.

......................................................................................................................................
......................................................................................................................................
(1)

(ii)

List the three characteristic properties of reactant particles which affect the rate of
reaction as described by the collision theory.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 4 marks)

3.

On the axes below sketch two Maxwell-Boltzmann energy distribution curves for the same
sample of gas, one at a temperature T and another at a higher temperature . Label both axes.
Explain why raising the temperature increases the rate of a chemical reaction.

................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)

4.

Hydrogen and nitrogen(II) oxide react according to the following equation.

2H2(g) + 2NO(g) N2(g) + 2H2O(g)
At time = t seconds, the rate of the reaction is
rate = k[H2(g)][NO(g)]

(i)

Explain precisely what the square brackets around nitrogen(II) oxide, [NO(g)], represent
in this context.
......................................................................................................................................
......................................................................................................................................
(1)

(ii)

Deduce the units for the rate constant k.

......................................................................................................................................
......................................................................................................................................
(1)
(Total 2 marks)

5.
Alex and Hannah were asked to investigate the kinetics involved in the iodination of propanone.
They were given the following equation by their teacher.
CH3COCH3(aq) + I2(aq) CH2ICOCH3(aq) + HI(aq)
Alexs hypothesis was that the rate will be affected by changing the concentrations of the
propanone and the iodine, as the reaction can happen without a catalyst. Hannahs hypothesis
was that as the catalyst is involved in the reaction, the concentrations of the propanone, iodine
and the hydrogen ions will all affect the rate.
They carried out several experiments varying the concentration of one of the reactants or the
catalyst whilst keeping other concentrations and conditions the same. Their results are shown
graphically below.

(a)

Discuss whether either Alexs or Hannahs hypothesis is correct.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

Explain why the reaction rate will increase with increasing temperature.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(c)

(i)

This reaction uses a catalyst. Sketch and annotate the Maxwell-Boltzmann energy
distribution curve for a reaction with and without a catalyst on labelled axes below.

(3)

(ii)

Describe how a catalyst works.

...........................................................................................................................
...........................................................................................................................
(1)
(Total 8 marks)

6.
Alex and Hannah were asked to investigate the kinetics involved in the iodination of propanone.
They were given the following equation by their teacher.
CH3COCH3(aq) + I2(aq) CH2ICOCH3(aq) + HI(aq)
Alexs hypothesis was that the rate will be affected by changing the concentrations of the
propanone and the iodine, as the reaction can happen without a catalyst. Hannahs hypothesis
was that as the catalyst is involved in the reaction, the concentrations of the propanone, iodine
and the hydrogen ions will all affect the rate.
They carried out several experiments varying the concentration of one of the reactants or the
catalyst while keeping other concentrations and conditions the same, and obtained the results
below.
Composition
by volume of
mixture /
3
cm
Experiment

Initial rate

1.00 mol
3
dm
CH3COCH3(
aq)

Water

10.0

1.00 mol
3 +
dm H (aq)

5.00 10
3
mol dm I2
in KI

/ mol dm s

60.0

10.0

20.0

4.96 106

10.0

50.0

10.0

30.0

5.04 106

5.0

65.0

10.0

20.0

2.47 106

10.0

65.0

5.0

20.0

2.51 106

(a)

Explain why they added water to the mixtures.

......................................................................................................................................
......................................................................................................................................
(1)

(b)

(i)

Deduce the order of reaction for each substance and the rate expression from the
results.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

Comment on whether Alexs or Hannahs hypothesis is correct.

...........................................................................................................................
...........................................................................................................................
(1)

(c)

Using the data from Experiment 1, determine the concentration of the substances used
and the rate constant for the reaction including its units.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(d)

(i)

This reaction uses a catalyst. Sketch and annotate the Maxwell-Boltzmann energy
distribution curve for a reaction with and without a catalyst on labelled axes below.

(3)

(ii)

Describe how a catalyst works.

...........................................................................................................................
...........................................................................................................................
(1)
(Total 11 marks)

7.

(a)

The production of ammonia is an important industrial process.

N2(g) + 3H2(g) 2NH3(g)

(i)

Using the average bond enthalpy values in Table 10 of the Data Booklet, determine
the standard enthalpy change for this reaction.
(3)

(ii)

The standard entropy values, S, at 298 K for N2(g), H2(g) and NH3(g) are 193, 131
1

and 192 JK mol respectively. Calculate S for the reaction and with reference
O
to the equation above, explain the sign of S .
(4)

(iii)

Calculate G for the reaction at 298 K.

(1)

(iv)

Describe and explain the effect of increasing temperature on the spontaneity of the
reaction.
(2)

(b)

The reaction used in the production of ammonia is an equilibrium reaction. Outline the
characteristics of a system at equilibrium.
(2)

(c)

Deduce the equilibrium constant expression, Kc, for the production of ammonia.
(1)

(d)

(i)

0.20 mol of N2(g) and 0.20 mol of H2(g) were allowed to reach equilibrium in a
3

1 dm closed container. At equilibrium the concentration of NH3(g) was

3

0.060 mol dm . Determine the equilibrium concentrations of N2(g) and H2(g) and
calculate the value of Kc.
(3)

(ii)

Predict and explain how increasing the temperature will affect the value of Kc.
(2)

(e)

Describe how increasing the pressure affects the yield of ammonia.

(2)

(f)

In practice, typical conditions used in the Haber process are a temperature of 500 C and
a pressure of 200 atmospheres. Outline why these conditions are used rather than those
that give the highest yield.
(2)

(g)

A catalyst of iron is used in the Haber process. State and explain how the catalyst affects
Kc and the position of equilibrium.
(3)
(Total 25 marks)

8.

The graph below shows how the volume of carbon dioxide formed varies with time when a
hydrochloric acid solution is added to excess calcium carbonate in a flask.

(i)

Explain the shape of the curve.

(3)

(ii)

Copy the above graph on your answer sheet and sketch the curve you would obtain if
double the volume of hydrochloric acid solution of half the concentration as in the
example above is used instead, with all other variables kept constant from the original.
Explain why the shape of the curve is different.
(4)

(iii)

Outline one other way in which the rate of this reaction can be studied in a school
laboratory. Sketch a graph to illustrate how the selected variable would change with time.
(2)

(iv)

Define the term activation energy and state one reason why the reaction between calcium
carbonate and hydrochloric acid takes place at a reasonably fast rate at room temperature.
(2)
(Total 11 marks)

9.
A piece of zinc was added to aqueous nitric acid and the volume of hydrogen gas produced was
measured every minute. The results are plotted on the graph below.

Which graph would you expect if the same mass of powdered zinc was added to nitric acid with
the same concentration?
(Total 1 mark)

10.

The Haber process enables the large-scale production of ammonia needed to make fertilizers.
The equation for the Haber process is given below.
N2(g) + 3H2 2NH3(g)
The percentage of ammonia in the equilibrium mixture varies with temperature.

(i)

Use the graph to deduce whether the forward reaction is exothermic or endothermic and
explain your choice.
(2)

(ii)

State and explain the effect of increasing the pressure on the yield of ammonia.
(2)

(iii)

Explain the effect of increasing the temperature on the rate of reaction.

(2)
(Total 6 marks)

11.

(a)

There are four structural isomers with the molecular formula C 4H9Br. One of these
structural isomers exists as two optical isomers. Draw diagrams to represent the threedimensional structures of the two optical isomers.
(2)

(b)

All the isomers can by hydrolysed with aqueous sodium hydroxide solution. When the
reaction of one of these isomers, X, was investigated the following kinetic data were
obtained.
3

Experiment

Initial [X] /mol dm

2.0 10

2.0 10

4.0 10

2.0 10

4.0 10

4.0 10

4.0 10

4.0 10

8.0 10

(i)

Initial [OH ] /mol

3
dm

Initial rate of
3
reaction /mol dm
1
min

Deduce the rate expression for the reaction.

(3)

(ii)

Determine the value of the rate constant for the reaction and state its units.
(2)

(iii)

State the name of isomer X and explain your choice.

(2)

(iv)

State equations for the steps that take place in the mechanism of this reaction and
state which of the steps is slow and which is fast.
(2)
(Total 11 marks)

12.

(a)

Define the term activation energy, Ea.

......................................................................................................................................
......................................................................................................................................
(1)

(b)

State two conditions necessary for a reaction to take place between two reactant particles.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(c)

Sketch an enthalpy level diagram to describe the effect of a catalyst on an exothermic

reaction.

(3)
(Total 6 marks)

13.

(i)

Define the term rate of reaction.

(1)

(ii)

State an equation for the reaction of magnesium carbonate with dilute hydrochloric acid.
(1)

(iii)

The rate of this reaction in (ii), can be studied by measuring the volume of gas collected
over a period of time. Sketch a graph which shows how the volume of gas collected
changes with time.
(1)

(iv)

The experiment is repeated using a sample of hydrochloric acid with double the volume,
but half the concentration of the original acid. Draw a second line on the graph you
sketched in part (iii) to show the results in this experiment. Explain why this line is
different from the original line.
(4)
(Total 7 marks)

14.

Nitrogen monoxide reacts at 1280 C with hydrogen to form nitrogen and water.All reactants
and products are in the gaseous phase.
(i)

The kinetics of the reaction were studied at this temperature. The table shows the initial
rate of reaction for different concentrations of each reactant.
3

experiment

[NO(g)]/mol dm
3
10

[H2(g)]/mol dm

5.00

2.00

1.25

10.00

2.00

5.00

10.00

4.00

10.00

10

Initial rate/mol dm
1
5
s 10

Deduce the order of the reaction with respect to NO and H 2, and explain your reasoning.
(4)

(ii)

Deduce the rate expression for the reaction.

(1)

(iii)

Determine the value of the rate constant for the reaction from Experiment 3 and state its
units.
(2)
(Total 7 marks)

15.

The gas-phase decomposition of dinitrogen monoxide is considered to occur in two steps.

Step 1: N2O(g) N2(g) + O(g)
Step 2: N2O(g) + O(g) N2(g) + O2(g)
The experimental rate expression for this reaction is rate = k [N2O].

(i)

Identify the rate-determining step.

(1)

(ii)

Identify the intermediate involved in the reaction.

(1)
(Total 2 marks)

16.

The conversion of CH3NC into CH3CN is an exothermic reaction which can be represented as
follows.
CH3NC transition state CH3CN
This reaction was carried out at different temperatures and a value of the rate constant, k, was
obtained for each temperature. A graph of ln k against 1/T is shown below.

(i)

Define the term activation energy, Ea.

(1)

(ii)

Construct the enthalpy level diagram and label the activation energy, Ea, the enthalpy
change, H, and the position of the transition state.
(3)

(iii)

Describe qualitatively the relationship between the rate constant, k, and the temperature,
T.
(1)

(iv)

Calculate the activation energy, Ea, for the reaction, using Table 1 of the Data Booklet.
(4)
(Total 9 marks)

17.

Graphing is an important method in the study of the rates of chemical reaction. Sketch a graph
to show how the reactant concentration changes with time in a typical chemical reaction taking
place in solution. Show how the rate of the reaction at a particular time can be determined.
(Total 4 marks)

18.

(a)

A solution of hydrogen peroxide, H2O2, is added to a solution of sodium iodide, NaI,

acidified with hydrochloric acid, HCl. The yellow colour of the iodine, I 2, can be used to
determine the rate of reaction.
H2O2(aq) + 2NaI(aq) + 2HCl(aq) 2NaCl(aq) + I 2(aq) + 2H2O(l)

The experiment is repeated with some changes to the reaction conditions. For each of the
changes that follow, predict, stating a reason, its effect on the rate of reaction.
(i)

The concentration of H2O2 is increased at constant temperature.

(2)

(ii)

The solution of NaI is prepared from a fine powder instead of large crystals.
(2)

(b)

Explain why the rate of a reaction increases when the temperature of the system
increases.
(3)
(Total 7 marks)

19.

Consider the following reaction studied at 263 K.

2NO(g) + Cl2(g) 2NOCl(g)

It was found that the forward reaction is first order with respect to Cl 2 and second order with
respect to NO. The reverse reaction is second order with respect to NOCl.

(i)

State the rate expression for the forward reaction.

(1)

(ii)

Predict the effect on the rate of the forward reaction and on the rate constant if the
concentration of NO is halved.
(2)

(iii)

1.0 mol of Cl2 and 1.0 mol of NO are mixed in a closed container at constant temperature.
Sketch a graph to show how the concentration of NO and NOCl change with time until
after equilibrium has been reached. Identify the point on the graph where equilibrium is
established.
(4)
(Total 7 marks)

20.

Consider the following reaction.

NO2(g) + CO(g) NO(g) + CO2(g)
Possible reaction mechanisms are:
Above 775 K:

NO2 + CO NO + CO2

slow

Below 775 K:

2NO2 NO + NO3

slow

NO3 + CO NO2 + CO2

Based on the mechanisms, deduce the rate expressions above and below 775 K.

fast

(Total 2 marks)

21.

State two situations when the rate of a chemical reaction is equal to the rate constant.
(Total 2 marks)

22.

Consider the following graph of ln k against for the first order decomposition of N 2O4 into
NO2. Determine the activation energy in kJ mol

for this reaction.

(Total 2 marks)

23.

Nitrogen(II) oxide reacts with hydrogen according to the following equation:

2NO(g) + 2H2(g) N2(g) + 2H2O(g)
The table shows how the rate of reaction varies as the concentrations of the reactants are
changed.

Experiment

Initial [NO] /mol

3
dm

Initial [H2] /mol dm

3

dm s

0.100

0.100

2.5310

0.100

0.200

5.0510

0.200

0.100

1.0110

0.300

0.100

2.2810

(a)

Initial rate /mol (N2)

3 1

Determine the order of reaction with respect to H2 and with respect to NO.
H2 ................................................................................................................................
NO ..............................................................................................................................
(2)

(b)

Write the rate expression for the reaction.

.....................................................................................................................................
(1)

(c)

Calculate the value for the rate constant, and state its units using the data from
experiment 1.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................

.....................................................................................................................................
(2)

(d)

A suggested mechanism for this reaction is as follows.

H2 + NO X

fast stepX + NO Y + H2O

slow stepY + H2 N2 + H2O
fast step

State and explain whether this mechanism agrees with the experimental rate expression in
(b).
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(4)

(e)

Explain why a single step mechanism is unlikely for a reaction of this kind.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(f)

Deduce and explain how the initial rate of formation of H 2O compares with that of N2.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 13 marks)

24.

Alkenes are important starting materials for a variety of products.

(a)

State and explain the trend of the boiling points of the first five members of the alkene
homologous series.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(b)

Describe two features of a homologous series.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)

25.

Below is a schematic diagram representing some reactions of ethene. The letters AD represent
the organic compounds formed from the reactants and catalysts shown.

Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC name of
compound C.

A:

B:

C:

IUPAC name: ..............................................................................................................

D:

(Total 5 marks)

26.

Describe a chemical test that could be used to distinguish between pent-1-ene and pentane.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)

27.

State and explain whether the following molecules are primary, secondary or tertiary
halogenoalkanes.
E:
................................................................................................................................................
................................................................................................................................................
F:
................................................................................................................................................
................................................................................................................................................
G:
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)

28.

Explain, using equations, the following steps in the free-radical mechanism of the reaction of
methane with chlorine.

Initiation
Propagation
Termination

................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)

29.

Butan-2-ol cannot be directly converted to 1,2-dibromobutane. The conversion can be carried

out in two stages by first converting butan-2-ol into X, which is then reacted with bromine.
butan-2-ol 1,2-dibromobutane

(a)

State the name and draw the structural formula of X.

Name: ..........................................................................................................................
Structure:

(2)

(b)

State an equation and the conditions needed for the conversion of butan-2-ol into X.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(c)

Describe the mechanism of the second stage of the conversion, which occurs when
bromine is added to X, using curly arrows to show the movement of electron pairs.
(3)

(d)

Butan-1-ol could be used instead of butan-2-ol. Compare the yield of 1,2-dibromobutane

expected for butan-1-ol with that obtained for butan-2-ol. Explain your answer.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 9 marks)

30. Compare the rates of hydrolysis of the compounds below and suggest two reasons for the
difference in reactivity.

................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)

31.

State the formula of the product formed when 2-chloropropane reacts with magnesium to form a
Grignard reagent and state the conditions required for this reaction to occur.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)

32.

Grignard reagents are often used to increase the length of the hydrocarbon chain in molecules.
An alternative way of doing this is to use cyanohydrins such as:

(i)

State the reagents that react to produce this compound.

......................................................................................................................................
(1)

(ii)

Draw the structural formula of the organic compound that is produced by the hydrolysis
of this cyanohydrin.

(1)
(Total 2 marks)

33.

(a)

State the class of compounds to which the substance below belongs and deduce a
balanced equation for its reaction with aqueous sodium hydroxide.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

Explain how the pH of an aqueous solution of the organic product from part (a) would
compare with the pH of aqueous ammonia of the same concentration.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)

34.

Two compounds, A and D, each have the formula C4H9Cl.

Compound A is reacted with dilute aqueous sodium hydroxide to produce compound B with a
formula of C4H10O. Compound B is then oxidized with acidified potassium manganate(VII) to
produce compound C with a formula of C4H8O. Compound C resists further oxidation by
acidified potassium manganate(VII).
Compound D is reacted with dilute aqueous sodium hydroxide to produce compound E with a
formula of C4H10O. Compound E does not react with acidified potassium manganate(VII).
Deduce the structural formulas for compounds A, B, C, D and E.

A:

B:

C:

D:

E:

(Total 5 marks)

35.

Deduce an equation for the reaction between propanoic acid and methanol. Identify the
catalyst and state the name of the organic compound, X, formed.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)

36.

2-chloro-3-methylbutane reacts with sodium hydroxide via an S N2 mechanism.Explain the

mechanism by using curly arrows to represent the movement of electron pairs.

(Total 4 marks)

37.

1-chlorobutane can be converted to a pentylamine via a two stage process.Deduce equations for
each step of this conversion including any catalyst required and name the organic product
produced at each stage.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)

38.

Describe the mechanism for the reaction of water with ethanoyl chloride.

(Total 4 marks)

39.

(a)

Describe the mechanism for the reaction of benzene with chlorine, using curly arrows to
show the movement of electron pairs, including the role of any other substance required
for the reaction to occur.

(4)

(b)

Methylbenzene and nitrobenzene also react with chlorine under similar conditions.
Explain the relative rates at which these two reactions occur.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 6 marks)

40.

(i)
Describe a chemical test that could be used to distinguish between propane and
propene. In each case state the result of the test.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(ii)

Under certain conditions propene can polymerize to form poly(propene). State the type of
polymerization taking place and draw a section of the polymer to represent the repeating
unit.
......................................................................................................................................
......................................................................................................................................
(2)

(iii)

Other than polymerization, state one reaction of alkenes which is of economic

importance.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 5 marks)

41.

Propan-1-ol and propan-2-ol are two structural isomers of C 3H8O.

(i)

State the equation for the complete combustion of C3H8O.

......................................................................................................................................
......................................................................................................................................
(2)

(ii)

Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by potassium

dichromate(VI). State any necessary conditions for the oxidation to occur and describe
the colour change during the oxidation process.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(iii)

State the name(s) and structure(s) of the organic product(s) that can be formed when each
of the alcohols is oxidized and suggest why one of the alcohols gives two organic
products and the other only gives one organic product.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(5)
(Total 10 marks)

42.

Benzene, C6H6, is a planar compound which differs from the non-planar structure of
cyclohexane, C6H12. The structures of benzene and the most stable form of cyclohexane are
represented below.

(a)

With reference to the compounds benzene, cyclohexane and 1,3-cyclohexadiene, state

which compound would contain the shortest carbon-carbon bond length.
......................................................................................................................................
(1)

(b)

Explain why it is more common for benzene to undergo substitution reactions than
addition reactions.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(1)
(Total 2 marks)

43.

Suggest why chloromethylbenzene, C6H5CH2Cl, reacts with warm aqueous sodium hydroxide,
NaOH, easily whereas for chlorobenzene, C 6H5Cl, stronger conditions such as high temperature
(e.g. 350 C) are needed.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)

44.

(a)

Draw the structural formulas of the major organic products formed in the following
reactions.
(i)

H3CCH=CH2 + ICl

(1)

(ii)

H3CCHO + HCN

(1)

(iii)

(1)

(iv)

CH3MgI

(1)

(b)

Draw the structural formula of the other product of the reaction in part (a) (i).

(1)

(c)

Identify each of the types of reaction in (a) as elimination, nucleophilic addition,

electrophilic addition, acid-base, addition-elimination or Grignard.
Reaction

Type

(a) (i)
(a) (ii)
(a) (iii)
(a) (iv)
(4)
(Total 9 marks)

45.

Identify a suitable catalyst for the dehydration reaction of ethanol, CH 3CH2OH, and describe
and explain the mechanism of the reaction using curly arrows to represent the movement of
electron pairs. State the name of the organic product formed.
Catalyst:
................................................................................................................................................
Mechanism:

Name of organic product:

................................................................................................................................................
(Total 4 marks)

46.

Deduce a two-step reaction pathway which can be used to convert butan-1-ol, CH 3(CH2)3OH,
into 1,2-dibromobutane, CH3CH2CHBrCH2Br. State the reagents used in each step and identify
the product formed in step 1.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)

47.

Which compound is optically active?

(Total 1 mark)

48.

There are several structural isomers with the molecular formula C 5H11Br.
(a)

Deduce the name of one of the isomers which can exist as enantiomers and draw threedimensional representations of its two enantiomers.
......................................................................................................................................

(3)

(b)

All the isomers react when warmed with a dilute aqueous solution of sodium hydroxide
according to the equation below.
C5H11Br + NaOH C5H11OH + NaBr
(i)

The reaction with 1-bromopentane proceeds by an S N2 mechanism. Describe this

mechanism using structural formulas and curly arrows to represent the movement
of electron pairs.

(3)

(ii)

The reaction with 2-bromo-2-methylbutane proceeds by an S N1 mechanism.

Describe this mechanism using structural formulas and curly arrows to represent
the movement of electron pairs.

(3)

(iii)

Explain why 1-bromopentane reacts by an SN2 mechanism whereas 2-bromo-2methylbutane reacts by an SN1 mechanism.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(3)

(iv)

Explain whether the boiling point of 1-bromopentane will be higher, lower or the
same as that of 2-bromo-2-methylbutane.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(3)

(v)

The product C5H11OH formed from the reaction with 1-bromopentane is warmed
with ethanoic acid in the presence of a few drops of concentrated sulfuric acid.

State the name of the type of reaction taking place and the structural formula of the
organic product.
...........................................................................................................................
...........................................................................................................................
(2)

(c)

If the conditions of the reaction in (b) are changed so that a hot solution of sodium
hydroxide in ethanol is used then a different reaction occurs. The reaction with 2-bromo2-methylbutane gives two different organic products. State the type of reaction taking
place and suggest the identity (name or structure) of these two products.Explain whether
or not they can exist as geometrical isomers.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(4)
(Total 21 marks)

49.

Dihalogenoalkanes can react with warm dilute potassium hydroxide solution to form diols.
These diols can react with dicarboxylic acids.
(i)

Deduce the equation for the reaction of benzene-1,4-dicarboxylic acid with the diol
formed from 1,5-dibromopentane.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(ii)

Outline the economic importance of the reaction of diols with dicarboxylic acids.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 4 marks)

50.

(a)

Identify all the major products, AD, in the following reactions.

(i)

CH3COCl + CH3CH2NH2 A + B
A:

B:

(1)

(ii)

2 + 2HNO3

+ D + 2H2O

C:

D:

(1)

(b)

C and D are isomers. Explain the mechanism of the reaction in (a) (ii), forming one of
these two isomers, using curly arrows to represent the movement of electron pairs.

(3)
(Total 5 marks)

51.

Benzene reacts with ethanoyl chloride, CH 3COCl, in the presence of an aluminium chloride
catalyst, AlCl3, in an acylation reaction. Explain the mechanism of the reaction, using curly
arrows to represent the movement of electron pairs. Include the formation of the electrophile.

(Total 4 marks)

52. Chloroethene, C2H3Cl, is an important organic compound used to manufacture the polymer
poly(chloroethene).
(i)

Draw the Lewis structure for chloroethene and predict the H C Cl bond angle.

......................................................................................................................................
(2)

(ii)

Draw a section of poly(chloroethene) containing six carbon atoms.

(1)

(iii)

Outline why the polymerization of alkenes is of economic importance and why the
disposal of plastics is a problem.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)

53.

(i)

Chloroethene can be converted to ethanol in two steps. For each step deduce an overall
equation for the reaction taking place.
Step 1:
......................................................................................................................................
......................................................................................................................................

Step 2:
......................................................................................................................................
......................................................................................................................................
(2)

(ii)

State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the
laboratory.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(iii)

State an equation, including state symbols, for the reaction of ethanoic acid with water.
Identify a Brnsted-Lowry acid in the equation and its conjugate base.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 7 marks)

54.

Ethanol is part of the homologous series of alcohols. Describe two features of a homologous
series.
(Total 2 marks)

55.

(a)

(i)

Below are four structural isomers of alcohols with molecular formula C 4H10O.
State the name of each of the isomers A, B, C and D.
(4)

(ii)

Determine the isomer that cannot be oxidized by acidified potassium

dichromate(VI), K2Cr2O7.
(1)

(iii)

Determine the isomer which can be oxidized to butanal.

(1)

(iv)

Determine the isomer which can be oxidized to butanone.

(1)

(v)

Suggest the structural formula of another isomer of C 4H10O.

(1)

(b)

(i)

Isomer A is formed by reacting 1-bromobutane with aqueous sodium hydroxide.

State whether the reaction would proceed via an SN1 or SN2 mechanism.
(1)

(ii)

Explain the mechanism named in part (b) (i) using curly arrows to represent the
movement of electron pairs.
(3)
(Total 12 marks)

56.

When bromoethane reacts with magnesium in the presence of a non-polar solvent, a Grignard
reagent is formed.
(a)

Give the equation for the reaction of this Grignard reagent with water.
......................................................................................................................................
......................................................................................................................................

(2)

(b)

This Grignard reagent can also react with aldehydes and ketones to give an initial product
which can then be hydrolysed by water to form an alcohol. State the names and formulas
of the alcohols formed when the Grignard reagent reacts with
(i)

ethanal.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

propanone.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)
(Total 6 marks)

57.

Alcohols can undergo elimination reactions in the presence of hot concentrated phosphoric acid.
(i)

Name the organic product formed when butan-1-ol undergoes an elimination reaction.
......................................................................................................................................
(1)

(ii)

Explain the mechanism for this elimination reaction using curly arrows to represent the
movement of electron pairs.

(Total 4 marks)

58.

Alkenes can undergo electrophilic addition reactions with bromine and with hydrogen bromide.
(a)

Explain how a bromine molecule is able to act as an electrophile.

......................................................................................................................................
......................................................................................................................................
(1)

(b)

Name the product formed when but-2-ene reacts with

(i)

bromine.
...........................................................................................................................
(1)

(ii)

hydrogen bromide.
...........................................................................................................................
(1)
(Total 3 marks)

59.

When but-1-ene reacts with hydrogen bromide, two possible organic products could be formed
but in practice only one organic product is obtained in high yield. Explain the mechanism for
this reaction using curly arrows to represent the movement of electron pairs and explain clearly
why only one organic product is formed.

.......................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)

60.

Benzene is sometimes represented as containing three alternate double and single bonds (Fig.1)
and sometimes represented as a hexagon with a circle in the middle (Fig.2).

Fig.1
(a)

Fig.2

Describe two different types of physical evidence which show that benzene does not
contain three double bonds.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

Explain how the reaction of benzene with bromine provides chemical evidence that
benzene does not contain three double bonds.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 3 marks)

61. (a)
Below are four structural isomers with molecular formula C4H9Br. State the name of
each of the isomers A, B, C and D.

(4)

(b)

(i)

Identify the isomer(s) which will react with aqueous sodium hydroxide almost
exclusively by an SN1 mechanism. State the meaning of the symbols in the term
SN1 mechanism.
(2)

(ii)

Using the formula RBr to represent a bromoalkane, state an equation for the rate
determining step of this SN1 reaction.
(1)

(iii)

Identify one isomer that will react with aqueous sodium hydroxide almost
exclusively by an SN2 mechanism. Draw the mechanism for this reaction using
curly arrows to represent the movement of electron pairs. Include the structural
formulas of the transition state and the organic product.
(4)

(c)

State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are affected
when the concentration of the sodium hydroxide is doubled.
(2)

(d)

State and explain how the rate of reaction of 1-bromobutane with sodium hydroxide
compares with that of 1-chlorobutane with sodium hydroxide.
(2)

(e)

Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a polarimeter
will distinguish between the isomers, and how their physical and chemical properties
compare.
(5)

(f)

(i)

State the type of reaction that occurs when isomer B, CH3CHBrCH2CH3, reacts
with a hot alcoholic solution of sodium hydroxide.
(1)

(ii)

Explain how the reaction in part (f) (i) occurs by drawing the mechanism, using
curly arrows to represent the movement of electron pairs and identify the two
possible organic products.

(4)
(Total 25 marks)

62.

Outline the different mechanisms involved in the manufacture of low-density poly(ethene) and
high-density poly(ethene).
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)

63.

Methylbenzene can be prepared from benzene and iodomethane.

State the catalyst used in this reaction and explain the mechanism of the reaction using curly
arrows to represent the movement of electron pairs.

Catalyst: ................................................................................................................................
(Total 4 marks)

64.

Methylbenzene reacts when heated with a mixture of concentrated sulfuric acid and
concentrated nitric acid.
(i)

Name the major organic products formed.

......................................................................................................................................

......................................................................................................................................
(1)

(ii)

Identify the electrophile in this reaction and explain how it is formed.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 4 marks)

65.

Alkenes are an economically and chemically important family of organic compounds.

(i)

The reaction of alkenes with bromine water provides a test for unsaturation in the
laboratory. Describe the colour change when bromine water is added to chloroethene.
(1)

(ii)

Deduce the Lewis structure of chloroethene and identify the formula of the repeating unit
of the polymer poly(chloroethene).
(2)

(iii)

Besides polymerization, state two commercial uses of the reactions of alkenes.

(2)
(Total 5 marks)

66.

But-2-ene can be converted to butan-2-one in two stages.

(i)

Draw the structural formulas of but-2-ene and butan-2-one.

(2)

(ii)

Deduce a reaction pathway for the two stages of the reaction. Your answer should include
the fully balanced equation for each stage of the reaction and the reagents and conditions

for the two stages.

(5)
(Total 7 marks)

67.

(i)

Deduce the structural formulas of the two alcohol isomers of molecular formula C3H8O.
Name each isomer and identify each as either a primary or a secondary alcohol.
(3)

(ii)

Oxidation of the alcohol isomers lead to the formation of different organic products.
Determine the structures of the organic products formed from the oxidation of each
alcohol isomer in (i) above and list the conditions required to obtain the different
products.
(5)
(Total 8 marks)

68.

Addition of hydrogen halides to unsymmetrical alkenes produces a mixture of halogenoalkanes.

The latter can be converted into Grignard reagents by reaction with magnesium metal and then
used for the preparation of various organic molecules with an increased number of carbon
atoms.
State in the boxes below, the formulas of the organic substances needed to complete the
following reaction pathways.
(Total 4 marks)

69.

Describe, using equations and curly arrows to represent the movement of electron pairs, the
mechanism of the reaction between propene and hydrogen bromide. Compare the relative
stabilities of the two intermediate carbocations which lead to the formation of the major and
minor products.

(Total 4 marks)

70.

Hydrolysis of aliphatic and aromatic halides occurs under different conditions.

State an equation, using structural formulas, to show the reaction of 1-chloro-2-(chloromethyl)
benzene with excess sodium hydroxide at room temperature.

(Total 2 marks)

71.

Deduce a two-step reaction pathway for the conversion of butan-1-ol into 1,2-dibromobutane.
State the appropriate equations, the reaction conditions and the reaction type for each step.
Step 1:
................................................................................................................................................
Reaction type for step 1:
................................................................................................................................................
Step 2:
................................................................................................................................................
Reaction type for step 2:
................................................................................................................................................
(Total 5 marks)

72.

The acidity of carboxylic acids depends on the carbon chain length and the nature of
substituents in their molecules. Table 15 of the Data Booklet provides some examples.
(a)

State and explain how the presence of halogen atoms in the hydrocarbon chain affects the
acidity of carboxylic acids.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(b)

State how the acidity of 3-chloropropanoic acid compares to that of propanoic acid and
chloroethanoic acid.
......................................................................................................................................
......................................................................................................................................
(1)

(c)

Suggest the pKa value for 3-chloropropanoic acid.

......................................................................................................................................
(1)
(Total 5 marks)

73.

Existence of isomers leads to diversity of organic compounds.

(a)

Describe what is meant by the term stereoisomers.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

1,3-dichlorocyclobutane exists as geometrical isomers, a form of stereoisomers.

(i)

Draw and name the two geometrical isomers of 1,3-dichlorocyclobutane.

...........................................................................................................................
(2)

(ii)

Identify the isomer with the higher boiling point and explain your reasoning.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(3)
(Total 7 marks)

74.

Halogenoalkanes undergo two major types of reaction leading to the formation of different
organic compounds.
(i)

1-bromopropane can be converted to 1-butylamine (butan-1-amine) in two stages.Draw

the structural formulas of 1-bromopropane and 1-butylamine (butan-1-amine).
(1)

(ii)

Deduce a reaction pathway for the two-stage conversion of 1-bromopropane to 1butylamine (butan-1-amine). Your answer should include an equation for each stage of
the reaction and the reaction conditions for the second stage.
(4)
(Total 5 marks)

75.

(i)

Describe the elimination of HBr from bromoethane. Your answer should include the
reagents, conditions and equation for the reaction.
(3)

(ii)

Explain the mechanism for the elimination of HBr from bromoethane.

(5)
(Total 8 marks)

76.

Alkylation of benzene is a common industrial process that allows substituents to be introduced

into the aromatic ring.
(a)

State an equation to show the reaction of benzene with chloromethane in the presence of a
Lewis acid.

(1)

(b)

Describe, using equations and curly arrows to represent the movement of electron pairs,
the mechanism of the above reaction.

(4)
(Total 5 marks)

77.

When benzene undergoes alkylation, more than one substituent can be introduced into the
aromatic ring. In contrast, acylation of methylbenzene usually gives a single organic product.
(a)

State an equation, using structural formulas, to show the reaction of methylbenzene with
ethanoyl chloride in the presence of a Lewis acid.

(2)

(b)

Give two reasons why other organic products do not form in this reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................

(2)
(Total 4 marks)

78.

State the structural formulas of the two organic products formed in the reaction below and state
the reaction type.

Reaction type: ........................................................................................................................

(Total 3 marks)

79.

The alkenes are an example of a homologous series.

(a)

State the name of the alkene shown.

......................................................................................................................................
(1)

(b)

Bromine water, Br2(aq), can be used to distinguish between the alkanes and the alkenes.
(i)

Describe the colour change observed when the alkene shown in part (a) is added to
bromine water.
...........................................................................................................................
...........................................................................................................................
(1)

(ii)

Draw the structural formula and state the name of the product formed.

...........................................................................................................................
(2)
(Total 4 marks)

80.

The polymerization of the alkenes is one of the most significant reactions of the twentieth
century.
(i)

Outline two reasons why the polymers of the alkenes are of economic importance.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(ii)

State the type of polymerization reaction shown by the alkene below.

......................................................................................................................................
......................................................................................................................................
(1)

(iii)

Deduce the structure of the resulting polymer showing three repeating units.

(1)

(iv)

Explain why monomers are often gases or volatile liquids, but polymers are solids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 6 marks)

81.

State the name of the product and identify the type of reaction which occurs between ethene and
hydrogen chloride.
(Total 2 marks)

82.

Consider the following sequence of reactions.

RCH3 RCH2Br RCH2OH RCOOH
RCH3 is an unknown alkane in which R represents an alkyl group.

(a)

The alkane contains 81.7 % by mass of carbon. Determine its empirical formula, showing
your working.
(3)

(b)

Equal volumes of carbon dioxide and the unknown alkane are found to have the same
mass, measured to an accuracy of two significant figures, at the same temperature and
pressure. Deduce the molecular formula of the alkane.
(1)

(c)

(i)

State the reagent and conditions needed for reaction 1.

(2)

(ii)

State the reagent(s) and conditions needed for reaction 3.

(2)

(d)

Reaction 1 involves a free-radical mechanism. Describe the stepwise mechanism, by

giving equations to represent the initiation, propagation and termination steps.
(4)

(e)

The mechanism in reaction 2 is described as SN2.

(i)

State the meaning of each of the symbols in S N2.

(1)

(ii)

Explain the mechanism of this reaction using curly arrows to show the movement
of electron pairs, and draw the structure of the transition state.
(3)
(Total 16 marks)

83.

Propan-1-ol has two structural isomers.

(i)

Deduce the structural formula of each isomer.

(2)

(ii)

Identify the isomer from part (i) which has the higher boiling point and explain your
choice. Refer to both isomers in your explanation.
(2)
(Total 4 marks)

84.

(a)

Describe the structure of benzene, C6H6.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)

(b)

State two pieces of evidence that support this description.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)

85.

Draw the structural formula of the major organic products, A and B, formed in the following
reactions.
(a)

CH3CH2CH=CH2 + HBr A
A:

(1)

(b)
B:

(1)
(Total 2 marks)

86.

Deduce a two-step reaction pathway which can be used to convert 1-bromopropane into
butanoic acid. Draw the structural formula of the organic product formed for each step and
identify the reagents involved.

(Total 4 marks)

87.

Deduce a two-step reaction pathway which can be used to convert propan-2-ol into 1,2dibromopropane. Draw the structural formula of the organic product formed for each step and
identify the reagents involved.

(Total 4 marks)

88.

(a)

State and explain which of the two compounds, phenol or ethanol, is the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

State and explain which of the two compounds, ethanoic acid or chloroethanoic acid, is
the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 5 marks)

89.

(a)

There are four structural isomers with the molecular formula C 4H9Br. One of these
structural isomers exists as two optical isomers. Draw diagrams to represent the threedimensional structures of the two optical isomers.
(2)

(b)

All the isomers can by hydrolysed with aqueous sodium hydroxide solution. When the
reaction of one of these isomers, X, was investigated the following kinetic data were
obtained.
3

Experiment

Initial [X] /mol dm

2.0 10

2.0 10

4.0 10

2.0 10

4.0 10

4.0 10

4.0 10

4.0 10

8.0 10

Initial [OH ] /mol

3
dm

Initial rate of
3
reaction /mol dm
1
min

(i)

Deduce the rate expression for the reaction.

(3)

(ii)

Determine the value of the rate constant for the reaction and state its units.
(2)

(iii)

State the name of isomer X and explain your choice.

(2)

(iv)

State equations for the steps that take place in the mechanism of this reaction and
state which of the steps is slow and which is fast.
(2)
(Total 11 marks)

90.

The equation for the conversion of benzene into chlorobenzene in the presence of aluminium
chloride is shown below.
C6H6 + Cl2 C6H5Cl + HCl
Explain the mechanism of this reaction, using curly arrows to represent the movement of
electron pairs.

(Total 4 marks)

91.

Deduce a two-step reaction pathway which can be used to convert methylbenzene into the
molecule BrCH2(C6H4)Br shown below.

Draw the structural formula of the organic product formed for the first step, identify the reagents
involved and state any specific reaction conditions or catalysts.

(Total 3 marks)

92.

(a)

State the formulas of the products E and F formed in the following reaction.
CH3COCl + 2CH3CH2NH2 E + F
E: .................................................................................................................................
F: .................................................................................................................................
(2)

(b)

Identify the nucleophile in the reaction in part (a).

......................................................................................................................................
(1)

(c)

State the type of reaction occurring in part (a).

......................................................................................................................................
(1)
(Total 4 marks)

93.

Three compounds with similar relative molecular masses are butane, propanal and propan-1-ol.
(i)

List the three compounds in order of increasing boiling point (lowest first) and explain
the differences in their boiling points.
(4)

(ii)

Predict, with an explanation, which of the three compounds is least soluble or miscible in
water.
(2)

(iii)

When propan-1-ol is oxidized using a warm acidified solution of potassium

dichromate(VI) two different organic products can be obtained. Deduce the name and
structural formula for each of these two products.
(3)

(iv)

Propan-2-ol is an isomer of propan-1-ol. Draw the structure of propan-2-ol.

(1)

(v)

Identify the class of alcohols that propan-2-ol belongs to and state the name of the organic
product formed when it is oxidized by an acidified solution of potassium dichromate(VI).
(2)
(Total 12 marks)

94.

Ethanol can be formed from ethene in a two step reaction:

(i)

State the name of the reagent used for step 1.

(1)

(ii)

State the name of the reagent and the conditions used for step 2.
(2)

(iii)

The mechanism involved in step 2 is SN2. Explain how the reaction proceeds using curly
arrows to represent the movement of electron pairs.
(3)

(iv)

Outline how ethanol is manufactured from ethene in industry and state one important
commercial use of ethanol.
(2)
(Total 8 marks)

95.

(a)

Describe the structure of benzene.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(4)

(b)

Cyclohexene, C6H10, reacts with hydrogen to form cyclohexane, C6H12.

C6H10 + H2 C6H12

H = 120 kJ mol

Calculate the enthalpy change of hydrogenation of benzene to cyclohexane, assuming it

has the 1,3,5-cyclohexatriene structure.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 5 marks)

96.

(i)

State the structure of the organic product for the following reaction and name the
mechanism for the reaction.

......................................................................................................................................
......................................................................................................................................
(2)

(ii)

Explain why bromobenzene, C6H5Br, does not react with OH .

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)

97.

Magnesium is a very electropositive metal which can be used in the formation of Grignard
reagents.
(i)

State the product when bromomethane and magnesium react together in a non-polar
solvent.
......................................................................................................................................
......................................................................................................................................
(1)

(ii)

Draw the structural formulas of the organic products formed in the following reactions.

CH3CH2MgBr

CH3CH2MgBr

H2O

H2O
(2)
(Total 3 marks)

98.

Draw the structural formulas of the organic products, AD, formed in the following reactions.

A:

B:

C:

D:

(Total 4 marks)

99.

Elimination reactions are common for tertiary alcohols. State the organic product formed in this
acid-catalysed reaction and explain the mechanism using curly arrows to show the movement of
electron pairs.
(Total 4 marks)

100. (a)
But-1-ene and 1-aminobutane (1-butylamine) can both be prepared from 1bromobutane.
(i)

State the equation (using structural formulas) and the necessary reagents and
conditions for the preparation of but-1-ene from 1-bromobutane.
(3)

(ii)

Identify the type of reaction and explain the mechanism for the preparation of but1-ene from 1-bromobutane using curly arrows to represent the movement of
electron pairs.
(3)

(iii)

State the equation (using structural formulas) for the preparation of 1-aminobutane
from 1-bromobutane. State the necessary reagents and conditions of the reaction.
(3)

(iv)

Explain the mechanism for the preparation of 1-aminobutane from 1-bromobutane

using curly arrows to represent the movement of electron pairs.
(4)

(b)

2-bromobutane and 2-bromo-2-methylpropane are two isomers of 1-bromobutane.

(i)

Draw the structures of the two mirror images of the isomer that can exhibit optical
isomerism.
(2)

(ii)

Describe how the two optical isomers can be distinguished practically using planepolarized light.
(2)

(iii)

Explain why the mechanism of the reaction will be different if 1-bromobutane is

replaced by 2-bromo-2-methylpropane to form 2-amino-2-methylpropane in the
reaction in part (a)(iv).
(3)
(Total 20 marks)

101. One form of nylon has the repeating unit:

(i)

Identify the circled functional group.

(1)

(ii)

Deduce the structures of the two monomers used to make this form of nylon.
(2)

(iii)

Nylon is a condensation polymer. Another condensation polymer can be formed by

reacting ethane-1,2-diol with benzene-1,4-dicarboxylic acid.

Deduce the equation for this reaction using n moles of each reactant.
(2)
(Total 5 marks)

102. Benzene, C6H6, undergoes electrophilic substitution reactions in order to synthesize other
compounds.
(i)

Describe, using an equation, the formation of the electrophile in the nitration of benzene.
......................................................................................................................................
......................................................................................................................................
(2)

(ii)

Describe the stepwise mechanism for the reaction of benzene with ethanoyl chloride,
CH3COCl in the presence of aluminium chloride, using curly arrows to show the
movement of electron pairs.

(3)
(Total 5 marks)

103. Chlorobenzene can be converted in two steps into the compound below.

State the reagents and conditions required for each step and state the structure of the compound
formed after the first step.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)

104. (i)

Methylbenzene can be converted in two steps into the compound below.

State the reagents and conditions required for each step.

......................................................................................................................................
......................................................................................................................................
(2)

(ii)

Deduce the formula of the product when the compound above reacts with hydroxide ions.
Explain your answer.

......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)

105. In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for cars called
gasohol.
(i)

Define the term average bond enthalpy.

(2)

(ii)

Use the information from Table 10 of the Data Booklet to determine the standard enthalpy
change for the complete combustion of ethanol.
CH3CH2OH(g) + 3O2(g) 2CO2(g) + 3H2O(g)
(3)

(iii)

The standard enthalpy change for the complete combustion of octane, C 8H18, is
1

5471 kJ mol . Calculate the amount of energy produced in kJ when 1 g of ethanol and
1 g of octane is burned completely in air.
(2)

(iv)

Ethanol can be oxidized using acidified potassium dichromate, K 2Cr2O7, to form two
different organic products.
CH3CH2OH A B
State the structural formulas of the organic products A and B and describe the conditions
required to obtain a high yield of each of them.
(4)

(v)

Deduce and explain whether ethanol or A has the higher boiling point.
(2)

(vi)

Ethene can be converted into ethanol by direct hydration in the presence of a catalyst
according to the following equation.
C2H4(g) + H2O(g) CH3CH2OH(g)
For this reaction identify the catalyst used and state one use of the ethanol formed other
than as a fuel.
(2)
(Total 15 marks)

106. (i)

State the name of one structural isomer of pentane.

(1)

(ii)

Sodium hydroxide reacts with 1-bromopentane via an SN2 mechanism.Describe the

mechanism of this reaction using curly arrows to represent the movement of electron
pairs.
(4)
(Total 5 marks)

107. Benzene is an important molecule containing delocalized electrons.

(a)

Explain the term delocalized electrons.

......................................................................................................................................
......................................................................................................................................
(1)

(b)

State and explain one piece of physical evidence and one piece of chemical evidence for
the presence of delocalized electrons in the structure of benzene.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(4)
(Total 5 marks)

108. Describe and explain the relative rates of the reactions of hydroxide ions with chlorobenzene,
C6H5Cl, and (chloromethyl)benzene, C6H5CH2Cl.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)

109. Predict and explain the structures of the major and minor products when hydrogen bromide is
added to 2-methylbut-2-ene, (CH3)2CCHCH3.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)

110. Draw the structural formulas of the two elimination products formed when butan-2-ol,
CH3CH2CH(OH)CH3 is heated with phosphoric acid.

(Total 2 marks)

111. (a)

Outline the formation of a Grignard reagent. Include any necessary conditions.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)

(b)

2-methylbutan-2-ol is formed by the reaction of a ketone with a Grignard reagent.Draw

the structural formula of 2-methylbutan-2-ol and deduce the structural formulas of the
ketone and the Grignard reagent used for the reaction.

......................................................................................................................................
......................................................................................................................................
(3)

(Total 5 marks)

112. Ethanol can be oxidized using acidified potassium dichromate, K 2Cr2O7, to form two different
organic products.
CH3CH2OH A B
State the structural formulas of the organic products A and B and describe the conditions
required to obtain a high yield of each of them.
(Total 4 marks)

113. Ethene can be converted into ethanol by direct hydration in the presence of a catalyst according
to the following equation.
C2H4(g) + H2O(g) CH3CH2OH(g)
For this reaction, identify the catalyst used and state one use of the ethanol formed other than as
a fuel.
(Total 2 marks)

114. Deduce a two-step synthesis for each of the following conversions. For each step, state the
structural formulas of all reactants and products and state the conditions used in the reactions.
(i)

Ethanol to ethyl ethanoate.

(2)

(ii)

Propene to propanone.
(2)
(Total 4 marks)

115. The reagents used in an elimination reaction are shown below.

Explain the mechanism of this reaction using curly arrows to represent the movement of
electron pairs.
(Total 3 marks)

116. (i)

Describe geometrical isomerism.

(1)

(ii)

Draw the geometrical isomers of but-2-ene.

(2)

(iii)

Draw the two enantiomers of butan-2-ol.

(2)
(Total 5 marks)

117. State the name of the product formed from the chlorination of nitrobenzene in which one
chlorine atom is introduced into the benzene ring. Describe and explain the effect of the nitro
group on the reaction. Your answer should include a comparison of the rate of chlorination of
benzene to that of nitrobenzene.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)

118. State the equation for the reaction of ethanoyl chloride, CH 3COCl, with sodium hydroxide.
Identify the mechanism for the reaction and explain it using curly arrows to show movement of
electron pairs.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)

119. (a)
The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 C, but
not necessarily in that order.

(i)

Isomer

Identify the boiling points for each of the isomers A, B and C and state a reason for
your answer.
A

Boiling point
...........................................................................................................................
...........................................................................................................................
(3)

(ii)

State the IUPAC names of isomers B and C.

B: .......................................................................................................................
C: .......................................................................................................................
(2)

(b)

Both C5H12 and C5H11OH can be used as fuels. Predict which compound would release a
greater amount of heat per gram when it undergoes complete combustion. Suggest two
reasons to support your prediction.
......................................................................................................................................
......................................................................................................................................

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 8 marks)

120. Halogenoalkanes can undergo substitution reactions with potassium hydroxide solution.
(i)

State an equation for the reaction of C 4H9Cl with KOH.

(1)

(ii)

Substitution reactions may occur by either of two mechanisms namely S N1 or SN2.

Outline the meaning of the term SN1.
(2)

(iii)

Predict the mechanism (SN1 or SN2) expected for the reaction of the following
halogenoalkanes with aqueous KOH.1-chlorobutane to form butan-1-ol2-chloro-2methylpropane to form 2 methylpropan-2-ol.
(2)

(iv)

Explain the mechanism of each reaction in part (iii) using curly arrows to represent the
movement of electron pairs.
(6)
(Total 11 marks)

121. (i)

Draw four structural isomers of molecular formula C 4H10O which contain the OH
group.
(4)

(ii)

On reaction with acidified potassium dichromate(VII), two of the isomers are oxidized in
two steps to produce different products. Draw the structural formula of the two products
formed from one of the isomers.
(2)

(iii)

A third isomer is oxidized in one step. Draw the structural formula of the organic product
formed.
(1)

(iv)

State the colour change that takes place in these oxidation reactions.
(1)

(v)

Identify the isomer which resists oxidation by acidified potassium dichromate(VI).

(1)
(Total 9 marks)

122. Consider the two amines methylamine, CH3NH2, and dimethylamine, (CH3)2NH.
(a)

Using Table 15 of the Data Booklet, state which of the amines is the more basic.
......................................................................................................................................
(1)

(b)

Explain the relative basicities of the two amines.

......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 3 marks)

123. Explain why chloroethanoic acid is a stronger acid than ethanoic acid.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................

................................................................................................................................................
(Total 2 marks)

124. Starting with chloromethane, outline one possible reaction pathway to synthesize ethanoic acid.
Your answer should include:

the reagents used

a relevant chemical equation for each step.

................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)

125. The carbonyl chemistry of both aldehydes and ketones involves a number of different types of
reactions.
(a)

State the formulas of the products A and B, formed in the following reactions.
(i)

(CH3)2CO A

H2O

A: ......................................................................................................................
(1)

(ii)
B: ......................................................................................................................
(1)

(b)

State the type of reaction involved in the formation of B and H2O in (a)(ii).
......................................................................................................................................
(1)
(Total 3 marks)

126. Alkenes commonly react by electrophilic addition reactions. Describe the mechanism of the
following reaction, using curly arrows to show the movement of electron pairs, and suggest the
reason for the formation of the major organic product, C.
CH2=CH(CH2CH3) + HI C

......................................................................................................................................
......................................................................................................................................
(Total 5 marks)

127. Alcohols can undergo elimination reactions. Describe the mechanism of the following reaction,
using curly arrows to show the movement of electron pairs, and identify the organic product, D.
CH3CH2OH + H3PO4 D

(Total 5 marks)

128. The compound C4H7Cl can exhibit stereoisomerism.

(i)

Draw the structural formulas of the two geometrical isomers of 1-chloro-but-2-ene.

(2)

(ii)

Explain why 1-chloro-but-2-ene shows geometrical isomerism.

(1)

(iii)

Draw the structural formula of one isomer of C4H7Cl that shows optical isomerism and
identify the chiral carbon atom with an asterisk (*).
(2)
(Total 5 marks)

129. The compound but-2-ene-1,4-dioic acid forms two geometrical isomers which have different
physical and chemical properties.
(i)

Explain the difference in the melting points of the two isomers.

(3)

(ii)

Outline how the two isomers behave differently when gently heated.
(1)
(Total 4 marks)

130. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an example of a
nucleophilic substitution reaction.
(i)

State whether this reaction is SN1 or SN2.

(1)

(ii)

Explain the mechanism of the reaction using curly arrows to represent the movement of
electron pairs.
(4)

(iii)

The organic product obtained in part (ii) can be reduced to form an amine.State an
equation for the reaction, naming the catalyst involved.
(2)
(Total 7 marks)

131. Bromoethane reacts with potassium hydroxide to undergo mainly a substitution reaction or an
elimination reaction depending on the reaction conditions used.
(i)

State an equation and the reaction conditions used to control the products formed in each
case.
(4)

(ii)

Explain the mechanism of the elimination reaction using curly arrows to represent the
movement of electron pairs.
(4)

(iii)

Under certain conditions, the major product obtained in the elimination reaction can
undergo polymerization. Identify the type of polymerization this major product
undergoes.
(1)
(Total 9 marks)

132. Both benzene and methylbenzene undergo electrophilic substitution reactions.State the formulas
of the reagents, EG, including any catalysts used, in the following conversions.

E: ...........................................................................................................................................

F: ...........................................................................................................................................

G: ...........................................................................................................................................
(Total 3 marks)

133. (i)

State whether OH can be described as an activating or deactivating group with respect to

aromatic electrophilic substitution reactions.
......................................................................................................................................
(1)

(ii)

Describe the directing effect of OH on a benzene ring in an aromatic electrophilic

substitution reaction.
......................................................................................................................................
(1)

(iii)

Explain the decreased reactivity due to the presence of the NO 2 group in an aromatic
electrophilic substitution reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)

134. (a)

List two characteristics of a homologous series.

.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(1)

(b)

Ethanol and ethanoic acid can be distinguished by their melting points. State and explain
which of the two compounds will have a higher melting point.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(c)

Draw the three isomers containing the alcohol functional group of formula C4H9OH.

(2)
(Total 5 marks)

135. The following is a computer-generated representation of the molecule, methyl 2hydroxy benzoate, better known as oil of wintergreen.

(i)

Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full structural
formula, including any multiple bonds that may be present.The computer-generated
representation shown does not distinguish between single and multiple bonds.
(2)

(ii)

In this representation, two of the carbon-oxygen bond lengths shown are 0.1424 nm and
0.1373 nm. Explain why these are different and predict the carbon-oxygen bond length in
carbon dioxide.
(2)

(iii)

Name all the functional groups present in the molecule.

(2)
(Total 6 marks)

136. (i)

State and explain the trend in the boiling points of the first six alkanes involving straightchains.
(2)

(ii)

Write an equation for the reaction between methane and chlorine to form chloromethane.
Explain this reaction in terms of a free-radical mechanism.
(5)
(Total 7 marks)

137. (i)

Identify the formulas of the organic products, AE, formed in the reactions, IIV:
I.

CH3(CH2)8OH + K2Cr2O7

II.

(CH3)3CBr + NaOH C

III.

(CH3)2CHOH + K2Cr2O7 D

IV.

H2C=CH2 + Br2 E
(5)

(ii)

H2C=CH2 can react to form a polymer. Name this type of polymer and draw the
structural formula of a section of this polymer consisting of three repeating units.
(2)
(Total 7 marks)

138. The molecular formula, C3H4Cl2 represents several isomeric compounds. Some isomers are
cyclic and some are unsaturated.
(a)

Draw the structures of two cyclic compounds that are structural isomers and state the
names of both isomers.

(2)

(b)

Two of the non-cyclic compounds have geometrical isomers. Draw the structures of these
compounds and their geometrical isomers.

(2)
(Total 4 marks)

139. The compound, 2-bromobutane, CH3CHBrCH2CH3, can react with sodium hydroxide to form

compounds F, G and H.
Compound F, C4H10O, exists as a pair of optical isomers. Compounds G and H, C4H8, are
structural isomers, and compound H exists as a pair of geometrical isomers.
(i)

Draw the structures of the two optical isomers of F.

(2)

(ii)

Outline the use of a polarimeter in distinguishing between the optical isomers.

(2)

(iii)

Draw diagrams to show the shapes of the two geometrical isomers of H.

(2)

(iv)

Draw the mechanism, using curly arrows to represent the movement of electron pairs, to
show the formation of G.
(3)
(Total 9 marks)

140. A compound, J, has the molecular formula C2H4O2 and is obtained from a reaction between
methanoic acid and methanol. Write an equation for this reaction and state the name of
compound J.
(Total 3 marks)

141. When hydrogen cyanide reacts with an aldehyde or a ketone the product molecule has one more
carbon atom.
(a)

Write an equation to show the addition of hydrogen cyanide to propanone.

.....................................................................................................................................
(1)

(b)

Describe, using curly arrows, a mechanism for the reaction of hydrogen cyanide with
propanone.

(4)

(c)

Write an equation for the acid hydrolysis of this product. State the two functional groups
in the organic product.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 7 marks)

151. The structure of benzene can be represented in two ways.

(a)

Use information from Table 9 of the Data Booklet to explain why structure B is used in
preference to structure A.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(b)

The enthalpy changes for the hydrogenation of cyclohexene and benzene are as follows.
C

(i)

6H10

+ H2 C6H12

H = 120 kJ mol

C6H6 + 3H2 C6H12

H = 210 kJ mol

Explain how this information can be used to support the statement that structure B
is more stable than structure A.
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

State what the circle in structure B represents.

...........................................................................................................................
...........................................................................................................................
(1)
(Total 5 marks)

152. Cyclohexanone can react with 2,4-dinitrophenylhydrazine in aqueous solution.

(a)

State the type of reaction that takes place.

.....................................................................................................................................
(1)

(b)

Complete the equation for this reaction using structural formulas for the products.
(2)

(c)

State why the product from this particular reaction can be used to confirm that the
reactant was cyclohexanone and not any other carbonyl compound.
.....................................................................................................................................
.....................................................................................................................................
(1)
(Total 4 marks)

153. Explain how the presence of the NO2 group on a benzene ring affects the rate of further
substitution.
...............................................................................................................................................
...............................................................................................................................................

...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
(Total 4 marks)