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SECTION A [15 MARKS]

Answer all questions in this section.

1. A type of chemical compound used to make the hard outer layer of golf balls has the
following structural formula.
O

H C – OCH3
C=C
H CH3
Which of the following statement is true?
A It is a cis isomer.
B It can react with 2,4-dinitrophenylhydrazine.
C It has only one chiral carbon centre.
D It only has structural isomers.
2. A mixture of 10 cm3 of methane and 10 cm3 of ethane is combusted in excess oxygen.
After cooling to room temperature, the gas residue is flowed through an aqueous
solution of potassium hydroxide. What is the volume of gas that is absorbed by the
aqueous potassium hydroxide?
A 15 cm3
B 20 cm3
C 25 cm3
D 30 cm3

3. In the preparation of ethene, ethanol is added drop by drop into a hot reagent Y. The
ethene formed is then passed through solution Z for purification process. Reagent Y
and solution Z are respectively
Reagent Y Solution Z
A Acidified K2Cr2O7 Diluted NaOH
B Concentrated H2SO4 Diluted H2SO4
C Concentrated H3PO4 Diluted NaOH
D Ethanolic NaOH Concentrated H2SO4

4. During the nitration of benzene, a hydrogen atom will be substituted with a nitro group.
Which of the following shows the bond arrangement of the carbon atom throughout the
reaction?
At the beginning In the intermediate complex At the end
A Plane Plane Plane
B Plane Tetrahedron Plane
C Plane Tetrahedron Tetrahedron
D Tetrahedron Plane Tetrahedron
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5. A liquid T is added to an alkaline solution of potassium manganate and refluxed. A

white precipitate that can be filtered out is formed when the mixture is left to cool and
acidified. Liquid T is most probably
A propanone
B 1,2-dibromoethane
C ethane-1,2-diol
D methylbenzene

6. 1 1 1
If moles of ethanol, moles of potassium bromide and moles of sulphuric
10 8 6

acid are used in the preparation of bromoethane, what is the maximum mass of the
product (bromoethane) formed?
A 109
g
6
B 109
g
10
C 109
g
46
D 109
g
10 x 46

7. Which of the following pairs of reagents, when reacted, will produce the organic
compound with the following structural formula?

OH

CH3 C C2H5

CH3

A CH3MgBr and CH3COCH3

B C2H5MgBr and CH3CH2CHO
C C2H5MgBr and CH3COCH3
D C4H9MgBr and HCHO
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8. Which of the following reagents can be used to differentiate both the following
compounds?

HO CH2OH
and

A Carbon dioxide
B Bromine water
C Ethanoyl chloride
D Diluted hydrochloric acid

9. The delicious taste of almond is caused by amygdalin when it is hydrolysed to form a

compound X. Continuous hydrolysis produces compounds Y and Z as shown by the
reaction scheme below.

C6H5 OH
Hydrolysis C Continuous
Amygdalin H CN Y+ Z
X hydrolysis

What could Y and Z be respectively?

A C6H5CH(OH)COOH and NH4+
B C6H5CH2OH and NH3
C C6H5COOH and NH3
D C6H5OH and CH3CN

10. A student discovered that trichloroethanoic acid, Cl3CCOOH that is stronger than
CH3COOH. This is because

A the electron accepting group, Cl, weakens the O – H bond so that H+ proton can
easily be released.
B the electron donating group, Cl, weakens the O – H bond so that H+ ions can
easily be released.
C the chlorine atom increases the negative charge of the carboxylate ion, thus H+
can easily be released.
D the resonance effect weakens the O – H bond and H+ ions are easily eliminated.
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11. A type of termite is found to release lardolure to attract the attention of other termites.
Lardolure can also be represented by the following structure.

RCH(CH3)–O–C–H

O
This compound can be broken down through acidic hydrolysis. What are the products of
the hydrolysis of this compound?

A RCH=CH2 + HCOOH
B RCH2CH3 + CO2
C RCH(CH3)COOH + HCOOH
D RCH(CH3)OH + HCOOH

12. A manufacturer wishes to make methyl salicylate, the aromatic liniment of oil of
wintergreen, from salicylic acid.

How is this esterification of salicylic acid best achieved?

A mixing it with cold ethanoyl chloride.

B warming it with anhydrous methanol.

C heating it under reflux with methanol and a little concentrated sulphuric acid.

D heating it under reflux with ethanoic acid and a little concentrated sulphuric acid.

13. Which of the following compounds releases a colourless gas when an aqueous solution
of sodium nitrate (III) and diluted hydrochloric acid are added to it?

A CH3CH2NH2

B (CH3)2NH

C (CH3)3N

D CH3NH3Cl
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14. An amine compound is formed according to the following reaction.

What are the reagents required in step I and step II of the above reactions?

Step I Step II

A Ammonia gas Hydrogen gas

B Ammonia gas Hydrogen cyanide

C Potassium cyanide Lithium tetrahydridoaluminate

D Aqueous ammonia gas Sodium hydroxide in ethanol

15. Which statements are true about the polymerization below?

Linear chain polymer Polymer with branched chain

Linear chain polymer Polymer with branched chain

A High density Low density

Low melting point High melting point
B High density Low density
High melting point Low melting point
C Low density High density
Low melting point High melting point
D Low density High density
High melting point Low melting point

Name : Class:

Answers for Section A

1. 2. 3. 4. 5. 6. 7. 8.

9. 10. 11. 12. 13. 14. 15.

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SECTION B [15 MARKS]
Answer all questions in this section.

16. Two isomers X and Y have the following structural formula.

X Y

(a) X and Y are both soluble in dilute acid. Give the formulae of the species formed when X and Y
are dissolved in dilute hydrochloric acid.

[2 marks]

(b) When compound X is boiled with aqueous sodium hydroxide, a gas that turns moist red litmus
blue is released.
Write the chemical equation for the reaction.

[2 marks]

(c) Show how you would synthesis X from benzoyl chloride.

[4 marks]
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17. (a) Diagram 1 shows the structure of serylalanine.

NH2 O
H
N
OH
OH O CH3

serylalanine

Diagram 1
Give the IUPAC name of two amino acids that form serylalanine. On the Diagram 1,
indicate and name the bond that links the two amino acid units.

……………………………………………………………………………………………...…..

.……………………………………………………………………………………………...…
[4 marks]
(b) Diagram 2 shows the structure of two monomers in a polymerisation.

COCl CH 2 OH

COCl CH 2 OH
Diagram 2

(i) Write the chemical equation to represent the polymerisation process that can occur
when the monomers react.

[1 mark]
(ii) State the type of polymerisation the monomers undergo.

.………… ……………………………………………………………………………………. . [1
mark]
(iii) The polymer formed is widely used in making fabric. Explain why this polymer
dissolve slowly when place in dilute mineral acid.
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SECTION C [30 MARKS]
Answer two questions only in this section.

18. (a) Alcohol A has the molecular formula C5H12O. Reaction of A with acidified
potassium dichromate (VI) produces a compound B, C5H10O2. Heating A over
alumina produces C, C5H10. Vigorous oxidation of C forms only one organic
compound D, C4H8O.
D forms orange precipitate with Brady’s reagent and is iodoform positive.
Deduce and give the structures for A, B, C and D.
Write equations for all reactions involved. [13 marks]

(b) Compound C from question (a) above can be polymerised. State the type of
polymerization that can occur with C and draw the repeating unit for the polymer of
C. [2 marks]

19. (a) Benzocaine is a local anaesthetic used by pharmacy which can be synthesis from 4-
aminobenzoic acid. Equation for the formation of benzocaine is given in the
equation below.
COOH COOCH2CH3
conc. H2SO4

+ CH3CH2OH + H2O

NH2 NH2

4-aminobenzoic acid benzocaine

Starting from benzene, propose a reaction schemes to synthesis 4-aminobenzoic
acid. Include also the reagent and condition for each step proposed. [7 marks]

(b) Benzene, toluene and nitrobenzene each undergoes acylation reaction in the
presence of aluminium trichloride.
Describe the mechanism of acylation in nitrobenzene. [5 marks]
Arrange the rate of acylation in benzene, toluene and nitrobenzene. Explain your
answer. [3 marks]
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20. (a) A fruity smelling liquid, X is hydrolysed in acid condition into Y and Z. Compound Y is
a monoprotic organic acid with relative molecular mass of 74. Compound Z can be
oxidised and gives positive iodoform test. On analysis compound Z was found to contain
60.0% carbon, 13.3% hydrogen and 26.7% oxygen by mass. The relative molecular mass
of Z is 60.

(i) Give the structural formula of compounds Y and Z. Explain your answer. [7 marks]

(ii) Deduce the structure of the fruity smelling liquid, X. [1 mark]

(b) P, C7H5N reacts with lithium aluminium hydride in ether to form a basic compound Q,
C7H9N. Compound Q reacts with a mixture of sodium nitrite and hydrochloric acid at 0oC
to liberate a colourless gas. When P is heated with dilute hydrochloric acid, an acidic
compound R, C7H6O2 is formed.

(i) Draw the structures of P, Q and R. [3 marks]

(ii) Write the chemical equation for the reaction of Q with the mixture of sodium nitrite
and hydrochloric acid at 0 oC. [2 marks]

(iii) Outline the conversion of compound R to C6H5CONH2. [2 marks]

-END OF QUESTION PAPER-

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Answers (Peperiksaan Percubaan Penggal Ketiga 2020):

1. D 2. D 3. C 4. B 5.D 6. B 7. C 8. B

9. A 10. A 11. D 12. C 13. A 14. C 15. B

SECTION B
Q Suggested Answer Marks
16 (a)

(b)

1M 1M

(c)

130atm
4

TOTAL: 8

17 (a) 2-amino-3-hydroxypropanoic acid 1

2-aminopropanoic acid 1
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NH2 O
H
N
OH

OH O CH3 2

serylalanine

Peptide linkage / peptide bond

(1 mark for arrow; 1 mark for name of bonding)

(b)(i) COCl CH2OH

O O

+ n C C O CH 2 CH 2 O + 2n H 2O
HCl 1
n
n
C OCl CH2OH

(b)(ii) Condensation polymerisation 1

(b)(iii) Because the ester linkage of the polymer is broken 1
TOTAL: 7

SECTION C
Q 18. (a) Marks
A is CH3 –CH2–CH –CH2OH 1
CH3
B is CH3 –CH2–CH –COOH
1
CH3
C is CH3 –CH2–C=CH2
CH3 1
D is CH3 –CH2–C=O
CH3 1
A is oxidized by to an acid B which indicates that A is a primaryalcohol./ not a tertiary 1
alcohol.
CH3 –CH2–CH –CH2OH K2Cr2O7/H+ CH3 –CH2–CH –COOH
1
CH3 ∆ CH3
A undergoes dehydration when heated over alumina to form C, an alkene. 1
CH3 –CH2–CH –CH2OH Al2O3 CH3 –CH2–C =CH2 + H20 1
CH3 ∆ CH3
Vigorous oxidation of C loses a carbon atom suggests that C is an alkenewiththeterminal 1
–C=CH2.
CH3 –CH2–C=CH2 KMnO4/H+ CH3 –CH2–C =O 1
CH3 ∆ CH3
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forms orange precipitate with Brady’s reagent, hence it has carbonyl group. 1
962/3
D is iodoform positive shows that D is a ketone with CH3C=O group. Confidential/Sulit
1
NO2
CH3 –CH2–C =O + H2N – NH NO2
1
CH3
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NO2
CH3 –CH2–C =N – NH NO2 + H2O
CH3

CH3 –CH2–C =O + I2 + NaOH CHI3 + CH3CH2COO– 1

CH3
Or

CH3 –CH2–C =O + 3I2 + 4NaOH CHI3 + CH3CH2COONa + 3NaI + 3H2O

CH3

MAX= 13 marks
(b) Addition polymerisation 1
CH2CH3 1
C – CH2
CH3
TOTAL: 15

Q 19. Acyl Chloride (Carboxylic acid derivatives) Marks

(a)

7
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5
[1]

TOTAL: 15

20. (a)(i) X is an ester which hydrolysed in dilute acid to form an alcohol and a 1
carboxylic acid. (1 mark)

Structure of Y:
 Y is CH3CH2COOH (1 mark) 1

Structure of Z:
 Z is an alcohol with methyl carbinol // methyl alcohol group. (1 mark) 1

Z: OH

H3C C R
H
 Determine the molecular formula of Z.

C H O
% 60.0 13.3 26.7
No. of mole = 5.0 = 13.3 = 1.7 (1 mark)

1
Ratio 3 8 1
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(1 mark)
1
(1 mark)

OH 1
Z: H3C C CH3 (1 mark)

H 1

(a)(ii) O CH3
X: 1
CH3 CH2 C O CH CH3

CN
(b)(i)

P: 1

CH2 NH2

Q:
1

COOH

R: 1

(b)(ii) CH2 NH2 CH2 OH CH2 Cl

NaNO 2, HCl H2O

<5oC
+ + N2 2

(minus 1 mark for each incorrect reagent or product)

(b)(iii) O O O
C OH C Cl C NH2
SOCl 2 NH3 2

1 mark 1 mark

TOTAL: 15