1

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 statement is true about the molecule?
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 cm 3 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 C 25 cm3
B 20 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 C ethane-1,2-diol
B 1,2-dibromoethane D methylbenzene

1 1 1
6. If moles of ethanol, moles of potassium bromide and moles of sulphuric acid are
10 8 6
used in the preparation of bromoethane, what is the maximum mass of the product
(bromoethane) formed?

109 109
A g C g
10 46

B g D g

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 C C2H5MgBr and CH3COCH3
B C2H5MgBr and CH3CH2CHO D C4H9MgBr and HCHO

8. Which of the following reagents can be used to differentiate both the following compounds?

HO CH2OH

A Carbon dioxide C Ethanoyl chloride

B Bromine water 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
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Amigdalin H CN Y+ Z
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.

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. The matsutake mushroom is a delicacy added to many Japanese foods. The spicy aroma
of this mushroom is due to methyl cinnamate, which can be prepared in the laboratory
according to the following reaction sequence.
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Which reagent could be used in step 1

A AlCl3 B CH3Cl C PCl5 D HCl

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

14. CH3CONH2 can be distinguished from CH3CH2NH2 by using

A alkaline iodine solution
B sodium hydroxide solution
C 2,4-dinitrophenylhydrazine solution
D acidified solution of potassium manganate (VII)

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
High melting point Low melting point
B High density Low density
Low melting point High melting point
C Low density High density
Low melting point High melting point
D Low density High density
High melting point Low melting point
Section B [15 marks]
Answer all questions in this section
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16. (a) Compound A goes through the following reaction. [3]

Bromine in
trichloroethane II
A CH3CHBrCHBrCH3 CH2=CH–CH=CH2

(i) Suggest one structural formula for compound A.

(ii) What is the type of reaction in Step II?

………………………………………………………………………………………….
.

(iii) State the reagents and conditions that are required in step II.

………………………………………………………………………………………………

………………………………………………………………………………………………
(b) When a mixture of cyclohexane and bromine is exposed to sunlight, white fumes are
released.
(i) Write the reaction mechanism involved. [3]

(ii) State the name of the organic product formed from the reaction. [1]

…………………………………………………………………………………………...

17. (a) Starting from butanone, CH3CH2CCH3, show the reaction scheme to synthesise the
 6

O
following compounds.
[6]

i. CH3CH2CHCH3

Cl

ii. CH3CH2C(OH)CH3

COOH

(b) Write equations for the reaction between benzaldehyde, –CHO and each of the
following compounds. [2]
(i) Acidified K2Cr2O7
(ii) H2N–N–H
NO2

NO2

Section C [15 marks]

Answer any two questions in this section.
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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]

(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]

19. (a) The structure below shows a compound X which is produced by pharmaceutical
industries to treat lung disease.
O

C
O
HO NH2

Name the functional groups besides the ester group present in the organic compound X.

[2]
Describe the simple chemical test to differentiate the functional groups that you stated
in X. Include the equation for the reaction involved in your answer.
[3]

(b) Write the structural formulae of the products formed from the acidic hydrolysis of the
following compound Y.
H O

N–C

CH3 [2]

(c) Write equations for all the reactions involved in the synthesis of the following
compounds.

(i) From 2-propanol to (CH3)2C(OH)COOH [5]

(ii) From benzene to CH3

CH–CH3

SO3H [3]
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20. (a) The boiling points of butanamine and pentane are 78 oC and 36oC respectively. Explain
why butanamine has a higher boiling point even though both these molecules have almost
the same relative molecular mass. [3]

(b) Compound E, C6H7N is dissolved in hydrochloric acid. Sodium nitrite is added to the
mixture at 5oC. When the mixture formed is poured into an alkaline phenol solution, a
yellow precipitate is formed. Suggest the identity of compound E and explain your
answer with equations where appropriate. [6]

(c) Suggest how you can change methanol to ethanamine. State the reaction conditions and
the reagents required. Write the equations involved. [6]

Answers (STK 2019 STPM P3 Trial)

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Section A:

1 D 4 B 7 C 10 A 13 A
2 D 5 D 8 B 11 D 14 B
3 C 6 A 9 A 12 C 15 A

Section B:

16. (a)(i) CH3 – CH = CH – CH3 [1]

(ii) Elimination reaction [1]
(iii) Ethanolic potassium hydroxide with heating / under reflux. [1]
(b)(i) Reaction mechanism:
hυ
Initiation step: Br – Br 2Br• [1]
Propagation step:

H + Br• → • + HBr
[1]

• + Br – Br → Br + Br•

Termination step:
Br• + •Br → Br2

• + • → [1]

• + •Br → Br

(ii)
Br bromocyclohexane [1]
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17. (i) LiAlH4 in

(i) CH3CH2CCH3 dry ether CH3CH2CHCH3 PCl5 CH3CH2CHCH3
(ii) H3O+
O [1] OH [1] Cl
[1]
Or HCN
(ii) CH3CH2CCH3 NaCN, H2SO4 H3CH2C(OH)CH3 H2O/H+ H3CH2C(OH)CH3
∆
O [1] CN [1] COOH
[1]

K2Cr2O7/H+
(b) (i) –CHO COOH
∆ [1]
H
(ii) C=O + H2N–N–H C=N–N–H + H2O
H NO2 NO2

NO2 NO2

[1]

18.

(a) A is CH3 –CH2–CH –CH2OH 1

CH3
B is CH3 –CH2–CH –COOH 1
CH3
C is CH3 –CH2–C=CH2 1
CH3
D is CH3 –CH2–C=O 1
CH3

A is oxidized by to an acid B which indicates that A is a primary alcohol./ not a 3 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 1
CH3 ∆ CH3

Vigorous oxidation of C loses a carbon atom suggests that C is an alkene with the 1
terminal –C=CH2.

CH3 –CH2–C=CH2 KMnO4/H+ CH3 –CH2–C =O 1

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CH3 ∆ CH3

D forms orange precipitate with Brady’s reagent, hence it has carbonyl group. 1
D is iodoform positive shows that D is a ketone with CH3C=O group. 1
NO2
CH3 –CH2–C =O + H2N – NH NO2
CH3

NO2 1
CH3 –CH2–C =N – NH NO2 + H2O
CH3

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

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

19.

(a) Amino group 1

Hydroxyl group 1
Add FeCl3 solution to compound X at room temperature. 1
Observation:
A purple solution is formed due to the presence of –OH group attached to the benzene 1
ring.
-NH2 group attached to the benzene ring has no observable change. 1
Equation:
O

C + FeCl3
O
HO NH2

O
1
C FeCl3
O
HO NH2

(b)
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H O

N+ – H and H – O – C
2
H
CH3

(c) (i) Cu/∆ or KMnO4/H+

CH3CH(OH)CH3 CH3COCH3 + H2O
(1) (1)

CH3COCH3 + HCN CH3C(CH3)(OH)CN

(1) (1)

CH3C(CH3)(OH)CN + H2O + H+ (CH3)2C(OH)COOH 5

(1) ∆

(ii)

+ H2SO4 (g)
(1) ∆ SO3H (1)
AlCl3 CH3
+ CH3CHCH3 CH–CH3
Cl
SO3H (1) SO3H
3

20.
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(a) hydrogen bonds between butanamine molecules. 1

weak van der Waals forces of attraction between molecules of pentane. 1

Hydrogen bond is stronger than van der Waals forces. 1

(b) C : H = 6 : 7 ( 1: 1). So, E is aromatic compound. 1

Compound E is phenylamine, NH2 . 1

NH2 + HCl NH3Cl 1

or NaNO2 + HCl
NH2 + HNO2 N2+Cl– + H2O 1
o
5C

NH3Cl + NaNO2 N2+Cl– + H2O

OH + OH– O– + H2O

N2+Cl– + O– N=N OH + Cl– [1]

2
Yellow precipitate (azo dye) [1]

(c) CH3OH + PCl5 → CH3Cl + POCl3 + HCl 2

2
CH3Cl + KCN + C2H5OH CH3CN
∆

(i) LiAlH4/dry ether

CH3CN CH3CH2NH2 2
+
(ii) H3O