Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

Suggested answers to in-text activities and unit-end exercises

Topic 8 Unit 31

Practice

P31.1 (page 92)

a) Substitution reaction
b) Br2  2Br•
c) Ultraviolet light / heat / radical initiator
d) i)

ii) Use a large excess amount of C6H5CH3

P31.2 (page 97)

1

2 a) Addition reaction
b) 1-bromo-1-methylcyclohexane
c)

d) Position isomerism

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

P31.3 (page 99)

a) i) CH3CH2CHBrCH3
ii) Addition reaction
b) i) NaOH(aq), heat under reflux
ii) Substitution reaction / hydrolysis

P31.4 (page 100)

a) primary alcohol; butan-1-ol
b) tertiary alcohol; 2-methylbutan-2-ol
c) secondary alcohol; cyclopentanol

P31.5 (page 106)

1 a) i)

ii) 2-chloro-2-methylpropane
b) i) CH3CH2CH2CH2I
ii) 1-iodobutane

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

P31.6 (page 111)

a) Dehydration
b) Heat, Al2O3 or conc. H2SO4 as catalyst
c) i)

ii) Position isomerism

P31.7 (page 118)

1

2 a) i) Isomer X
ii)

iii) CH3CH2CH(OH)CH3(aq) + [O]  CH3CH2COCH3(l) + H2O(l)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

b) i) Isomers W and Y
ii) Distil off the aldehydes as they form.
Use excess alcohol.
To prevent further oxidation. /
To prevent the formation of carboxylic acid.

P31.8 (page 122)

1 a) Vanillin contains a carbonyl group while vanillyl alcohol contains a
hydroxyl group.
b) i)

ii)

c) The reaction was exothermic.

d) Collect the product by filtration. Wash the product with ice-cold water.
Transfer the product to a piece of filter paper to air dry.

2 a) Any one of the following:

• Warm each isomer with acidified K2Cr2O7(aq).
Q turns the dichromate solution from orange to green.
There is no observable change for P.
• Warm each isomer with acidified KMnO4(aq).
Q turns the permanganate solution from purple to colourless.
There is no observable change for P.
b) Any one of the following:
• Add Br2(aq) to each isomer separately and shake.
The yellow-brown Br2(aq) turns colourless quickly when added to
isomer R.
There is no observable change for isomer S.
• Add cold acidified dilute KMnO4(aq) to each isomer separately and
shake.
The purple KMnO4(aq) turns colourless quickly when added to
isomer R.
There is no observable change for isomer S.

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

P31.9 (page 130)

1

2 a) Acidified K2Cr2O7(aq)
b)

c) Reduction

P31.10 (page 134)

1 a) CH3CH2COOH + CH3OH
b)

c)

d) CH3CH2CH2COO–Na+ + NH3

2 In acid hydrolysis,
• the acid is a catalyst;
• the reaction is reversible / does not go to completion;
• the carboxylic acid (not its salt) is produced.

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

Discussion (page 130)

Add each liquid into NaHCO3(aq).
Only CH3CH2COOH reacts to give a colourless gas (carbon dioxide).
Add Br2(aq) to each of the three other liquids and shake Br2(aq).
Only CH2=CHCH2OH turns the yellow-brown Br2(aq) colourless quickly.
Warm the last two liquids with acidified K2Cr2O7(aq) separately.
Only CH3CH2CH2OH turns the orange acidified K2Cr2O7(aq) green.
CH3COCH3 gives negative results in all the above chemical tests.

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

Unit Exercise (pages 140-154)

1 a) haloalkane
b) addition
c) hydrolysis
d) substitution
e) heating with excess conc. H2SO4
f) dehydration / elimination
g) oxidation
h) carboxylic acid
i) 1 LiAlH4 / dry diethyl ether
2 H+(aq)
j) reduction
k) ketone
l) oxidation
m) NaBH4 / H2O
n) reduction
o) alkane
p) Br2, sunlight
q) substitution reaction
r) heat, concentrated sulphuric acid as catalyst
s) esterification
t) heat under reflux, dilute sulphuric acid
u) hydrolysis
v) heat, moderately concentrated sulphuric acid or hydrochloric acid
w) hydrolysis

2 C

3 A

4 C

5 D

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

6 D Options A and B — These secondary alcohols can be oxidised to ketones.

Option C — This tertiary alcohol CANNOT be oxidised.
Option D — This primary alcohol gives an aldehyde and then a carboxylic
acid upon oxidation

7 C is a primary alcohol while is a tertiary alcohol.

When each alcohol is mixed with hot acidified K2Cr2O7(aq), only

produces a colour change from orange to green.

gives no observable change.

8 D Reduction of butanone (a ketone) gives butan-2-ol (a secondary alcohol).

2-chlorobutane undergoes hydrolysis to give butan-2-ol when heated with
NaOH(aq).

9 B Reduction of an aldehyde produces a primary alcohol while the reduction of

a ketone produces a secondary alcohol.
2-methylbutan-2-ol is a tertiary alcohol. Hence it could NOT be produced
by the reduction of an aldehyde or a ketone.

10 C The oxidation of a secondary alcohol forms a ketone.

11 A The reduction of an aldehyde by NaBH4 gives a primary alcohol.

12 D Propanone CANNOT be oxidised when heated with acidified K2Cr2O7(aq).

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

13 B For butan-2-ol, water can be lost in two ways:

14 A (1) CH3CH=CHCH2CHO is an aldehyde. It can be oxidised by

acidified K2Cr2O7(aq).
(2) CH3CH=CHCH2CHO has stereoisomers.

15 B (1) The compound is a carboxylic acid. It undergoes neutralisation with

aqueous ammonia to form a salt.
(2) NaBH4 is NOT strong enough to reduce carboxylic acids. LiAlH4 is a
stronger reducing agent and can be used to reduce carboxylic acids.
(3) The compound and ethyl propanoate are functional group isomers.

16 A

17 A

18 A

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

19 a) (1)

b)

(1)

c)

(1)
d)

(1)

e)

(1)
f)

(1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

20 a) substitution reaction / hydrolysis (1)

b) dehydration / elimination (1)
c) oxidation (1)
d) esterification / condensation (1)
e) hydrolysis (1)
f) reduction (1)

21

22 a) carbon-carbon double bond (1)

ester group (1)
b) It contains a carbon-carbon double bond. (1)
c) From yellow-brown to colourless (1)
d) i) Stereoisomers are isomers whose atoms are bonded together in the
same way but are arranged differently in space. (1)

ii) (1)
iii) Incomplete combustion occurs. (1)
Carbon is formed.

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

23 a)

(1)
2-bromopentane (1)
b)

(1)

2-bromo-2-methylbutane (1)
c)

(1)

1-bromo-1-methylcyclohexane (1)

24 a)

(1)

b)

(1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

25

26 a) 3-bromopropene (1)
b) i) reagent X — NaOH(aq) (1)
reagent Y — acidified K2Cr2O7(aq) (1)
ii) pro-2-enal (1)

27 a) carbon monoxide / carbon; (1)

water (1)
b) Hydroxyl group (1)
c) C6H11OH + PCl5  HCl + C6H11Cl + POCl3 (1)
d) Cyclohexene
Add Br2(aq) to cyclohexene and shake. (1)
The yellow-brown Br2(aq) turns colourless quickly. (1)
Cyclohexanol
Warm with acidified K2Cr2O7(aq). (1)
The orange dichromate solution turns green. (1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

28 a) Aluminium oxide / concentrated sulphuric acid (1)

b)

(1)

c) Structural isomers (1)

d)

(1)

29 a) X contains a carbonyl group. (1)

Y contains a carboxyl group. (1)
b) Y can form hydrogen bonds, which are stronger than the van der Waals’
forces in X. (1)

30 a) Effervensence occurs due to the presence of the –COOH group. (1)

b) The yellow-brown Br2(aq) turns colourless quickly due to the presence of
the carbon-carbon double bond. (1)
31 a) X contains a hydroxyl group. (1)
b) X is not a carboxylic acid. (1)
c) X is a tertiary alcohol. (1)
d)

(1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

32 a)

(1)
b) i) dehydration / elimination (1)
ii)

(1)

iii) It contains a carbon-carbon double bond. There is restricted rotation of

atoms or groups around a carbon-carbon double bond. (1)
There are two different atoms or groups on each carbon atom of the
carboncarbon double bond. (1)
c)

(1)

33 a) i) The solution changes from orange to green. (1)

ii) Propanone (1)
b) i) NaBH4 / H2O (1)
ii) Propanone (1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

34 a) Any one of the following:

• Add Br2(aq) to each compound separately and shake. (1)
The yellow-brown Br2(aq) turns colourless quickly when added to
compound Z.
There is no observable change for compound W. (1)
• Add cold acidified dilute KMnO4(aq) to each compound separately and
shake. (1)
The purple KMnO4(aq) turns colourless quickly when added to
compound Z.
There is no observable change for compound W. (1)
b)

35 a) Structural formula of compound X:

(1)
Reagent for Reaction 2: NaBH4 / H2O (1)
b) Colour changes from orange to green (1)
c) To ensure that a carboxylic acid is formed. /
To prevent the formation of an aldehyde. (1)

36 a) 2CH3CH2COOH + Na2CO3  2CH3CH2COO–Na+ + CO2 + H2O (1)

b)

(1)
c)
(1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

37 a) 2,6-dimethylhept-5-enal (1)
b) i)

(1)
addition (1)

ii)

(1)
reduction (1)

38 a) Methylpropanoic acid (1)

b) • As a catalyst (1)
• To remove the water formed (1)
c) Methyl butanoate has a lower boiling point than butanoic acid.
Van der Waals’ forces in methyl butanoate are less strong compared with
hydrogen bonds in butanoic acid. (1)

39 a) Carbonyl group (1)

b) i) Acidified K2Cr2O7(aq) (1)
The hydroxyl group in X will be converted to a carbonyl group when
warmed with acidified K2Cr2O7(aq).
The mixture with X changes from orange to green. (1)
ii) Br2(aq) (1)
An addition reaction occurs.
Br2(aq) changes from yellow-brown to colourless when added to Y. (1)
c) Heat
Aluminium oxide or concentrated sulphuric acid as catalyst (1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

40 a) i) Concentrated sulphuric acid (1)

ii)

(2)
b) i) 2-butyl ethanoate (1)
ii)

(1)
41

(1)

(1)

42 a)

b) Pent-2-enoic acid (1)

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Topic 8 Chemistry of Carbon Compounds Mastering Chemistry

c) i)

(1)

ii)

(1)

43 a) i) –OH (1)
ii)

(1)

b)

(1)

(1)

c)

(1) (1)

44 Answers for the HKDSE question are not provided.

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