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Section A [15 marks]

Answer all questions in this section.
1. What would happen if 1 mole of ethane is mixed with 6 moles of chlorine in the dark
at room temperature?
A.
B.
C.
D.

No reaction
CH3Cl and HCl are formed
CH3CCl3and HCl are formed
CCl3CCl3 and HCl are formed

2. Which of the following are the steps involve in the preparation of 1,2-dibromobutane
from butan-1-ol?
A.
B.
C.
D.

Dehydration followed by addition.

Dehydration followed by oxidation.
Oxidation followed by hydrolysis.
Hydrolysis followed by addition.

3. Which of the following statement is not true about Freon-12?

A.
B.
C.
D.

Refrigerant
Aerosol propellant
Depletion of ozone
Not decomposed by light

4. Which of the following pairs of compounds are distinguished by means of the

triiodomethane test?
A.
B.
C.
D.

CH3CH2OH and CH3CH(OH)CH3

CH3CH2CH2OH and CH3CH(OH)CH3
CH3OH and CH3CH2CH2OH
C6H5CH2OH and CH3OH

5. Which of the following reagents can be used to distinguish between phenol and
cyclohexanol?
A.
B.
C.
D.

Ethanoyl chloride
Dilute hydrochloric acid
Dilute sulphuric acid
Aqueous bromine

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6. Stereoisomerism is classified into geometrical isomerism and optical isomerism.

Given the following compounds ;
I
\

H
II
\

H
III
\

CH3CH3
/
C C
/
\
CH2CH3
CH3 CH2CH3
/
C C
/\
CH3
CH2CH3 CH3
/
C C
/
\

HCH3
IV
CH2CH3 H
\
/
C C
/
\
CH2CH3H
Which of the following pair of compounds show geometrical isomerism?
A.
B.
C.
D.

I and II
I and III
II and IV
III and IV

7. Which of the following structures of esters and water are formed when ethanoic acid is
refluxed with methanol enriched in oxygen-18, CH318OH?
A. CH3C O CH3+ H218O

O
B. CH3C O CH3+ H2O

18
O
C. CH3C 18O CH3+ H2O

18
O
D. CH3C 18O CH3+ H2O

O
3

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8. Two polymers, X and Y, has the following structures :

Polymer X
CH2

CH CH2

OCOCH3

CH CH2 CH

OCOCH3
OCOCH3

Polymer Y
O
O
O

OCH CH2 C OCH CH2 CO CH2 CH2 C

Which of the following are monomers of X and Y?
Monomer X
A. CH2 CHCH2

OCOCH3
B. CH2 CH2

OCOCH2CH3
C. CH2 CH

COOCH3
D. CH2 CH

OCOCH3

Monomer Y
HOOCCH2CH2 COOH

HOCH2CH2OH

CH3CH2CH2COOH

HOCH2CH2 COOH

9. N phenylbenzamide,

A.
B.
C.
D.

C
l
a
Nn
Hd

can be prepared by reacting

C
O
N
H

C2
H
O
2
N
C
a
H
O
n
NH
C
2d
CO
l
a
nH
dand

C
l

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10. An organic compound, Y, has a relative molecular mass of 60. It reacts with sodium
hydroxide solution to give a soluble product. When treated with phosphorous
pentachloride, it produces an organic compound that reacts vigorously with water. The
structural formula of Y is
[RAM : H, 1; C, 12; O, 16; F, 19]
A.
B.
C.
D.

CH3COOH
CH3CH2CH2OH
CH2CHCH2F
HCOOCH3

11. Geraniol can be isolated from the oil of geranium and has the following structure :
(CH3)2CCHCH2CH2C(CH3)CHCH2OH
It would be expected to
A.
B.
C.
D.

produce an alkane on reaction with hydrogen, using a nickel catalyst.

decolourise a solution of bromine in tetrachloromethane.
reduce Fehlings solution.
dissolve in aqueous sodium hydroxide, forming sodium salt.

12. Which of the following terms best describes the change that takes place during the
action of aqueous hydrogen chloride on ethyl ethanoate?
A.
B.
C.
D.

Hydrolysis
Neutralisation
Redox
Polymerisation

13. Which of the following compounds could undergo an elimination reaction when
treated with hot ethanolic potassium hydroxide?
A.
B.
C.
D.

(CH3)3CBr
Br3CCBr3
(CH3)2CCBr2
(CH3)3CC(CH3)3

14. Complete hydrolysis of a peptide gives 5 amino acids represented by letters, P, Q, R,

S, and T. The following fractions are obtained when the same peptide is partially
hydrolysed.
Partial hydrolysis
Peptide

TS + QP + RT + SQ

Which of the following sequence might be the arrangement of amino acids in the
peptide?
A. P T S Q R
B. R T S P Q
C. Q P T S R
5

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D. R T S Q P
15. Natural rubber is a type of natural polymer. Below are statements regarding natural
rubber.
I
II
III
IV

Natural rubber is made up of cis and trans isoprene.

Natural rubber is hardened by heating with sulphur.
In hardened rubber, sulphur atoms form bridges between hydrocarbon
chain.
Natural rubber is produced from Guttapercha trees.

Which of the following statements are true?

A.
B.
C.
D.

I and II
I and IV
II and III
III and IV

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Section B [15 marks]

Answer all questions in this section.
16. Alanine (2-aminopropanoic acid) and phenylalanine (2-amino-3-phenylpropanoic
acid) are two types of amino acids found in proteins.
(a)

Draw the structure of the zwitterion of phenylalanine

[1 mark]
(b) Draw two different possible dipeptides which might be formed by alanine and
phenylalanine. Name both dipeptides.

[4 marks]
(c) The form of amino acid depends on the pH of the solution. Draw the most
probable form of glutamic acid, HOOC(CH2)2CH(NH2)COOH.
(i)

at pH 2

(ii)

at pH 13

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17. (a)

[2 marks]
Draw the structural formula of the organic compound(s) formed in each of the
reaction below.
I2 / NaOH
(i)

CH3CH2COCH3
HCN

(ii)
Fehlings or
(iii)

CH3CHO
Tollens reagent
[3 marks]

(b)

For each reaction (a)(i) and (a)(iii) above, comment on the uses of the
reactions, whether for identification, synthesis, or to differentiate between
compounds.
_______________________________________________________________
_______________________________________________________________
_______________________________________________________________
_______________________________________________________________
_______________________________________________________________
_______________________________________________________________
[5 marks]

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Section C [30 marks]

Answer any two questions in this section
18. (a)

What do you understand by the terms cis-trans isomerism and optical

isomerism?
[3 marks]

(b)

State and explain clearly, if any, the types of isomerism shown by the
following compounds :
(i)
CHBrCHCH2

(ii)
(iii)

CH3CHCHCH2CH(OH)CH3
(CH3)2CCHCH2CH(OH)CH2CHC(CH3)2
[8 marks]

(c)

Outline a possible synthesis of the compound 3-methylbenzoic acid from

methylbenzene.
[4 marks]

19. (a)

Explain fully the observations of the following experiments with phenol :

(i)
Phenol undergoes bromination more readily than benzene.
[5 marks]
(ii)
Phenol is a weaker acid than 4-nitrophenol.
[5 marks]

(b)

A haloalkane, 2-chloro-2-methylpropane undergoes nucleophilic substitution

reaction with hydroxide ion. Name the type of nucleophilic substitution it
undergoes and explain fully its mechanism.
[5 marks]

20. Describe and explain what happens in each of the following experiments. Write a
balanced equation for reactions that occur.
(a)
Propene is passed into cold, dilute aqueous potassium manganate(VII).
[4 marks]
(b)
Phenylamine is shaken with an excess of dilute hydrochloric acid and the
mixture is evaporated.
[4 marks]
(c)
A mixture of hexane and bromine in an inert solvent is exposed to ultraviolet
light.
[4 marks]
(d)
Ethanamide is heated with aqueous sodium hydroxide.
[3 marks]
END OF QUESTION PAPER
Prepared by,

Checked by,

Verified by;

(IRNI HAFIZAN IBRAHIM BEY)

(KHOO POO KIEW)

(HOW HUAN YEW)

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Subject Teacher
UnitPre-U Program

SULIT
Head of Chemistry Panel
Pre-U Program

10

Head of Science
Pre-U Program