GERAK GEMPUR 3 TERM 3 (2013)

SECTION A

1 When 10 cm3 of a hydrocarbon, Q , was completely burnt in 80 cm3 of oxygen, the

volume of carbon dioxide produced was 40 cm3. The volume of unreacted oxygen was found to be 15
cm3. All volumes were measured at the same temperature and pressure.
The molecular formula of hydrocarbon Q is
A C2H6 B C3H6
C C4H8 D C4H10

2 Which of the following statements is true of toluene ?

A All the carbon atoms undergo hybridization of sp2

B All the atoms are in the same plane
C There are 15 sigma bonds and 3 pi bonds in toluene
D No observable change is observed when toluene is heated with acidified
potassium manganate(VII)

3 Which of the following compounds does not exhibit stereoisomerism ?

A CH3CH2CH(CH3)CH=CH2
B CH3C=CHCH3

CH3
C CH3CHBr

OH
D CH3CH=CHCHO

4 The total number of isomers (including stereoisomers) for a molecule with molecular
formula of C3H4Cl2 is
A 7 B 6
C 5 D 3

5 Which of the following species is a nucleophile ?

A. AlCl3 B. BF3
C. CH2=CH2 D. CH3CH2+

6 Which of the following sets of organic compounds is arranged correctly in increasing

order of acid strength ?

A. C2H5OH, C6H5OH, CH3COOH , ClCH2COOH

B. ClCH2COOH, CH3COOH, C6H5OH, C2H5OH
C. CH3COOH, ClCH2COOH, C2H5OH , C6H5OH
D. C6H5OH, CH3COOH, C2H5OH , ClCH2COOH

7 Consider the following reaction scheme.

I II
CH3 CHCl2 CHO

Which of the following sets of reagents and conditions is the most suitable to be used in the
conversion of toluene to benzaldehyde as shown above ?
 I II
A. excess Cl2, Fe NaOH(aq), reflux
B. excess Cl2, uv, boil KOH(aq), reflux
C. excess Cl2, NaOH(aq), ethanol, reflux
D. excess Cl2, uv, boil Cu, 400

8 For the reaction shown below ,

2-methyl-2-bromopropane + NaOH(aq) Y + NaBr

heat
which of the following statement is true of the reaction ?

A. The product ,Y is 2-butanol

B. It is a second order reaction
C. A change in the concentration of the hydroxide ion does not affect reaction rate
D. Rate of reaction increases when concentration of the hydroxide ions is increased

9 Which of the following can be used to distinguish ethanal from benzaldehyde ?

A. 2,4-dinitrophenylhydrazine
B. Tollens reagent
C. acidified potassium manganate(VII)
D. Fehlings solution

10 Which of the following reagents is used to distinguish between 2-methyl-2-propanol

and phenol ?
A. acidified potassium dichromate(VI) solution
B. iodine in aqueous sodium hydroxide
C. aqueous bromine
D. ethanoyl chloride

11 The structural formula of citric acid is shown below.

OH

HOOCCCH2COOH

COOH

Which of the following statements is not true of citric acid ?

A. 1 mole of citric acid reacts with 4 moles of sodium hydroxide
B. Citric acid reacts with sodium carbonate and carbon dioxide gas is evolved
C. Citric acid reacts with sodium metal and hydrogen gas is liberated
D. Citric acid is resistant towards oxidation by hot acidified KMnO4

12 The following compound :

CH3N-C- can be prepared from

CH3
 A. CH3COOH and NHCH3

B. (CH3)2NH and COCl

C. (CH3)2NH and CH2OH

D. CH3NHC and CH3Cl

13 Which of the following reagents can be used to convert bromopropane to propene ?

A. Aqueous sodium hydroxide B. Concentrated sulphuric acid

C. Ethanolic sodium hydroxide D. Ethanolic potassium cyanide

14. Lactic acid can be formed from ethanol as shown in the reaction scheme below.
Name the types of reaction that occur in step I and step lll.

Step I Step lll

A Oxidation Hydrolysis
B Reduction Esterification
C Condensation Oxidation
D Dehydration Condensation

15. Which of the following compound is formed when ethanoy clhloride is reacted with
 SECTION B

16. (a) Compound Q has molecular formula of C4H8O. Compound Q does not decolourise aqueous
bromine but it forms an orange precipitate with 2,4-dinitrophenylhydrazine.
Isomer of Q, P, forms a yellow precipitate when treated with iodine in aqueous sodium hydroxide.
P is also resistant to oxidation by acidified potassium dichromate(VI) aqueous solution.

(i) Draw all the possible structures of Q. [2 marks]

(ii) Identify P by writing its structural formula. [1 mark ]

(iii) Write a chemical equation for the reaction of P with iodine in aqueous sodium hydroxide.
[1 mark ]

(iv) State the observation when Q is added to Tollens reagent and the mixture is then warmed in a
hot water bath. Also write chemical equation for the reaction involved.
[2 marks]
.

(b) Compound Q and isomer P react with hydrogen cyanide in the presence of a base at 10-20 C to
form cyanohydrin.
(i) State the type of reaction that takes place. [1 mark ]

.
(ii) By using chemical equations, write the reaction mechanism for the reaction of Q with
hydrogen cyanide. [2 marks]
17. (a) Adrenaline is a hormone that acts as a stimulant .It has the structural formula shown below

(i) State the type of isomerism that can exist in the adrenaline molecule. [1 mark]

(ii) Draw the structural formula of the product formed when adrenaline reacts with
[2 marks ]

NaOH HCl
Structural formula Structural formula

(b) Adrenaline can be synthesized from X via the following steps:

(i) State the type of reaction that is involved in step 1 [1 mar]

(ii) State the condition(s) required for step2 . [1 mark]

 SECTION C
(Answer 2 questions from this section)

18 (a) Compound Z is a dibasic acid that is found in fruits and it has the following composition by mass.
C, 35.8 % ; H, 4.5% ; O, 59.7%

The relative molecular mass of Z is 134.

Z reacts with ethanol in the presence of concentrated sulphuric acid under reflux to give E, C8H14O5.

Compound E evolves hydrogen gas when treated with sodium metal and it also reacts with acidified
potassium dichromate(VI) solution to form compound F.

Compound F produces an orange precipitate with 2,4-dinitrophenylhydrazine but shows no reactions

with Fehlings or Tollens reagent.

(i) Determine the empirical formula and molecular formula of Z. [4 marks]

(ii) Suggest the structural formula of Z, E and F. Also write chemical equations for all the
reactions involved. [8 marks]

(b) Compound B has been identified as being responsible for the distinctive aroma of raspberries. The
structural formula of compound B is as shown below.

HO CH2CH2COCH3
Compound B

(i) Name the functional groups in compound B. [2 marks]

(ii) Draw the structural formula of the organic product formed when compound B reacts with
aqueous bromine. [1 mark ]

19 (a) Chloroethene or vinylchloride is used in the making of polymer PVC.

(i) Draw the structural formula of chloroethene. [1 mark ]

(ii) Draw 2 repeating units of polymer PVC. State the type of polymerization involved.
[2 marks]
(iii) Suggest a reason why PVC might break down when exposed to concentrated
solution of sodium hydroxide but poly(ethene) does not. [2 marks]

(b) Give a chemical test to distinguish between ethylamine, C2H5NH2 and aniline, C6H5NH2
[3 marks]
(c) The structural formula of compound G is shown below. G can be used as a dye. It can be prepared
from an amine and a phenol under suitable conditions.
CH3
H3C N=N OH
CH3
Compound G

(i) Draw the structural formula of the amine and phenol that can be used in the preparation of G.
[2 marks]
 (ii) State the reagents and conditions that are used in the preparation of G. Also write chemical
equations for the reactions involved [4 marks]

(iii) State the type of reaction that has taken place in (c)(ii) [1 mark ]

20.

++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++
ANSWERS
SECTION A

Q A Q A Q A
1 6 11

2 7 12

3 8 13

4 9 14

5 10 15

Section B

Q 16
. a) (i) Q = CH3CH2CH2CHO , CH3CH(CH3)CHO [2]
(ii) P = CH3COCH2CH3 [1]
(iii) CH3COCH2CH3 + I2 + OH- CHI3(s) + CH3CH2COO- [1]
(iv) Silver mirror is formed [1]

RCHO + [Ag(NH3)2]+ + OH- Ag(s) + RCOO- [1]

(b) (i)

17 (a) i) optical isomerism

(ii)
(b) ( i) nucleophilic addition
(ii) dry ether, room temperature

18. (a)(i) C H O
No of moles : 35.8 4.5 59.7 . [1]
12 1 16
= 2.89 4.5 3.73
Simplest ratio 4 6 5
E.f of Z = C4H6O5. [1 ]
M.f of Z = ( C4H6O5.)n

n (C4H6O5) = 134
n=1 [1]
M.f of Z = C4H6O5 [1]

Z = HOOCCH(OH)CH2COOH [1]

E = CH3CH2OCOCH(OH)CH2COOCH2CH3 [1]

F = CH3CH2OCOCOCH2COOCH2CH3 [1]

HOOCCH(OH)CH2COOH + 2 CH3CH2OH CH3CH2OCOCH(OH)CH2COOCH2CH3

Z + 2H2O E [1]

2 CH3CH2OCOCH(OH)CH2COOCH2CH3 + 2 Na 2CH3CH2OCOCH(ONa)CH2COOCH2CH3 [1]

E + H2(g)

CH3CH2OCOCH(OH)CH2COOCH2CH3 CH3CH2OCOCOCH2COOCH2CH3 [1]

E F

E is a secondary alcohol because F is a ketone. [1]

OO
O2N
CH3CH2OCCCH2COOCH2CH3 + H2NNH NO2

O2N
O NNH NO2

CH3CH2OCCCH2COOCH2CH3 + H2O [1]

(b)(i) Phenolic and carbonyl group(ketone) [1] +[1]

(ii)

Br [1]
HO CH2CH2COCH3
Br Total 15
19.(a) (i) CH2=CHCl [1]

(ii) H H H H
C C C C
H Cl H Cl [1]

Addition polymerisation [1]

(iii) PVC has polar CCl bond that can be hydrolysed when reacts with NaOH [1]
Polyethene does not have polar bond since it is a non-polar hydrocarbon. [1]

(b) Reagent : Add aqueous bromine or bromine water at room temperature and shake the mixture.
[1]
Observation : Aniline decolourises bromine and a white precipitate is formed. No observable change shown
by ethylamine [1]
Br
Equation : NH2 + 3 Br2 [1]
Br NH2 + 3HBr
(c) (i) CH Br [1]+[1]
3 NH2 CH3
CHO
3
(ii) Reagent : HNO2 or NaNO2,HCl H
Condition : 0-50C [2]

Equations: CH3 NH2 + HNO2 + HCl CH3 N2+Cl- + 2H2O

[1]
CH3 CH3
CH3 N2+Cl- + CH3 N=N
CHO3 O
+ HCl CH
[1] H 3
H
(iii)Electrophilic substitution [1]