SuppEx Solution 3B E

Topic 8 Chemistry of Carbon Compounds
Part A Unit-based exercise
Unit 29 An introduction to the chemistry of carbon compounds
Fill in the blanks

1 carbon-carbon double bond
2 hydroxyl
3 carbonyl
4 carboxyl
5 O
C O
6 O
C N

7 permanent dipole-permanent dipole attractions
8 hydrogen bonds
True or false
9 F The carbonyl group in a ketone is NOT in the terminal position of the carbon chain.
10 T
11 F The polar bromoalkane molecules can interact with water molecules, but the attractive forces set up are
not as strong as the hydrogen bonds between water molecules. Hence bromoalkanes are only slightly
soluble in water.

12 F Due to the hydrogen bonding between alcohol molecules and water molecules, alcohols with less carbon
atoms (C1, C2, C3 and some isomers of C4) are miscible with water in all proportions.
The following diagram shows the hydrogen bonding between ethanol molecules and water molecules:
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)
0
)
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13 T Ketones CANNOT form hydrogen bonds between their own molecules while alcohols can.
The following diagram shows the hydrogen bonding between ethanol molecules:
)
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LFZ
0
IZESPHFOCPOE
14 F The van der Waals’ forces between molecules increase as the number of carbon atoms in the molecules
increases. Thus, the volatility of aldehydes decreases as the number of carbon atoms in their molecules
increases.
15 T Esters are polar compounds.
16 T Amines are classified as primary, secondary or tertiary depending on how many substituents are connected
to the nitrogen atom.
Ethanamine (CH3CH2NH2) has one alkyl group connected to the nitrogen atom. Thus, it is a primary
amine.

17 T Molecules of primary amines can form hydrogen bonds with water molecules. As a result, simple primary
amines are very soluble in water.
The following diagram shows the hydrogen bonding between an ethanamine molecule and water
molecules:
)

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0
/
)
)
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)
)
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) LFZ

0
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)
Amines with long carbon chains resemble alkanes more and are less soluble in water.
Thus, the water solubility of amines decreases as the number of carbon atoms in their molecules
increases.
18 T The following diagram shows the hydrogen bonding between an ethanamide molecule and water
molecules:
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LFZ
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Multiple choice questions
19 B Option B — Molecular formula C2H4O2 represents an ester.
H C O CH3

20 A
Homologous series Functional group
Amides –CONH2
Amines –NH2
O
Ketones
C
21 A Option A — LSD has an amide functional group.
CH2CH3
O N
CH2CH3
N
CH3
H
HN
22 D Option A, B and C — The compound has an amide functional group, an amine functional group and
a carboxyl group.
amide
functional group
CH3 O H O
H N C C N C C OH
carboxyl group
H H H H
amine
functional group

O O O O
CH3CH2 C CH 3CH32 is an
OCH
23 B CCHester
OCH
3CH 2CH
while
3 2 CH3CH
C 2CH2
OH C OH is a carboxylic acid.
Option A — The compounds belong to different homologous series.

Option B — The molecular formula of both compounds is C4H8O2. Thus, they have the same relative
molecular mass.
Option C — The ester contains an ester functional group while the carboxylic acid contains a carboxyl
group.

5
24 C Option C — H CH3 H CH3
1 2 3 4
H C C C C H
H CH3 H CH3
The parent chain contains 5 carbon atoms, i.e. pentane.

TWO methyl groups are attached to the second carbon atom and one to the fourth carbon
atom, i.e. 2,2,4-trimethylpentane.
25 C Option C — CH3
7,8
C2H5
1 2 3 4 5 6
CH3 CH CH2 CH2 CH2 CH CH3
The parent chain contains 8 carbon atoms, i.e. octane.

TWO methyl groups are attached to the second and sixth carbon atom, i.e.
2,6-dimethyloctane.
26 D Option D —
1
2
6
5
3
4
TWO methyl groups are attached to the first and third carbon atoms of the cyclohexane,
i.e. 1,3-dimethylcyclohexane.
27 D Option D — CH3 H
5 4 3 2
H
CH3 C C C 1
CH3
H
The parent chain contains 5 carbon atoms, with the double bond between the second and
third carbon atoms, i.e. pent-2-ene.
A methyl group is attached to the fourth carbon atom, i.e. 4-methylpent-2-ene.
4 3
28 D Option D — CH3 C C CH3
5,6 1,2
C2H5 C2H5
The parent chain contains 6 carbon atoms, with the double bond between the third and
fourth carbon atoms, i.e. hex-3-ene.
TWO methyl groups are attached to the third and fourth carbon atoms, i.e.
3,4-dimethylhex-3-ene.

29 A Option A — Br
2 1
H3C C CH3
3
CH2
4
CH3
The parent chain contains 4 carbon atoms, i.e. butane.

A bromo group and a methyl group are attached to the second carbon atom, i.e.
2-bromo-2-methylbutane.
30 C Option C — I Br
1 2
H C C CH3
3,4
H C2H5

An iodo group is attached to the first carbon atom, a bromo group and a methyl group to
the second carbon atom, i.e. 2-bromo-1-iodo-2-methylbutane.
31 A Option A — H CI CH3 H H H H
7 6 5 4 3 2 1
H C C C C C C C Br
H H H H H H H
The parent chain contains 7 carbon atoms, i.e. heptane.

A bromo group is attached to the first carbon atom, a methyl group to the fifth one, and
a chloro group to the sixth one, i.e. 1-bromo-6-chloro-5-methylheptane.
32 D Option D — H H H Br
4 3 2 1
H C C C C H
H Br Cl H

TWO bromo groups are attached to the first and third carbon atoms, and a chloro group
to the second one, i.e. 1,3-dibromo-2-chlorobutane.
33 C Option C — H H Br
1 2 3
H C C C H
4,5
C2H5
The parent chain contains 5 carbon atoms, with the double bond between the first and
second carbon atoms, i.e. pent-1-ene.
A bromo group is attached to the third carbon atom, i.e. 3-bromopent-1-ene.
1
34 C Option C — CH3
2
H C OH
3
H3C C H
4,5
C2H5
The parent chain contains 5 carbon atoms, with the –OH group attached to the second
carbon atom, i.e. pentan-2-ol.
A methyl group is attached to the third carbon atom, i.e. 3-methylpentan-2-ol.
35 B Option B — CH3 H H H H
6 5 4 3 2 1
CH3 C C C C C OH
CH3 H H H H
The parent chain contains 6 carbon atoms, with the –OH group attached to the first carbon
atom, i.e. hexan-1-ol.
TWO methyl groups are attached to the fifth carbon atom, i.e. 5,5-dimethylhexan-1-ol.
36 D Option D — 1 2 3 4 5
CH3 CH CH2 CH CH3
OH
The parent chain contains 5 carbon atoms, with the –OH group attached to the second
carbon atom, i.e. pentan-2-ol.
A phenyl group is attached to the fourth carbon atom, i.e. 4-phenylpentan-2-ol.
37 B Option B — CH3 H H H
6 5 4 3 2 1
CH3 C C C C CHO
H H H H
The parent chain of this aldehyde contains 6 carbon atoms, i.e. hexanal.
A methyl group is attached to the fifth carbon atom, i.e. 5-methylhexanal.
38 C Option C — 4 3
CH2CHCH2CHO
2 1
CH3
The parent chain of this aldehyde contains 4 carbon atoms, i.e. butanal.
A methyl group is attached to the third carbon atom and a phenyl group to the fourth one,
i.e. 3-methyl-4-phenylbutanal.

39 A Option A — 1CH 2CCH
3 4 5
3 2CH2CH3
The parent chain of this ketone contains 5 carbon atoms, with the carbonyl group at the
second carbon atom, i.e. pentan-2-one.
40 B Option B — 1CH 2CCH

3
3 2I
The parent chain of this ketone contains 3 carbon atoms, i.e. propanone.
An iodo group is attached to the parent chain, i.e. iodopropanone.
There is NO need to specify the position of the iodo group in this case because the group
must be attached to one of the carbon atoms next to the carbonyl group.
41 D Option D — O
C CH3
This is a ketone containing 2 carbon atoms and one phenyl group, i.e. phenylethanone.
1 2 3 4 5
42 A Option A — HOOC–CH2–CH2–CH2–COOH
This dioic acid contains 5 carbon atoms, with two carboxyl groups attached to the first and
fifth carbon atoms, i.e. pentane-1,5-dioic acid.
Notice that the last letter ‘e’ of the corresponding alkanes are retained in dioic acids.
43 B Option B — O
CH3 CH2 CH2 C O CH2 CH3
this part comes from this part comes

butanoic acid from ethanol
Thus, the IUPAC name of this ester is ethyl butanoate.
44 D Option D — O CH3
CH3 C O CH2 CH CH3
this part comes from this part comes from

ethanoic acid 2-methylpropan-1-ol
Thus, the IUPAC name of this ester is 2-methylpropyl ethanoate.

45 A Option A — O
CH3 C O
this part comes from this part comes from

ethanoic acid cyclohexanol
Thus, the IUPAC name of this ester is cyclohexyl ethanoate.
46 C Option C — this part comes from this part comes from

benzoic acid methanol
COOCH3
Thus, the IUPAC name of this ester is methyl benzoate.
47 D Option D — O
CH3 O C CH2 CH3
this part comes this part comes

from methanol from propanoic acid
Thus, the IUPAC name of this ester is methyl propanoate.
48 C Option C —
N
The above amine has three alkyl groups connected to the nitrogen atom. Thus, it is a tertiary
amine.
49 C Option C — CH3 H
3 2 1
CH3 C C NH2
H H
The parent chain of this amine contains 3 carbon atoms, with the –NH2 group attached to
the first carbon atom, i.e. propan-1-amine.
A methyl group is attached to the second carbon atom, i.e. 2-methylpropan-1-amine.
50 B Option B — O
5 4 3 2 1
CH3CH2CH2CH2C
NH2
The parent chain of this amide contains 5 carbon atoms, i.e. pentanamide.

3 2 1
51 D Option D — CH2 CHCH2OH
This compound contains two functional groups (–OH group and C=C group).
The –OH group attached to the first carbon atom is the principal functional group. The C=C
group takes the suffix form -en-. Thus, its IUPAC name is prop-2-en-1-ol.
52 A Option A — CHO
1
6 2
5 3
OH
This compound contains two functional groups (–CHO group and –OH group) attached to
a benzene ring.
The –CHO group is the principal functional group, i.e. benzaldehyde.
The carbon atom of the benzene ring bearing the –CHO group is assigned number 1.
The –OH group attached to the fourth carbon atom takes the prefix hydroxy, i.e.
4-hydroxybenzaldehyde.
53 B Option B — OH
6 5 4 3 2 1
CH3 CH CH2 CH CH2 COOH
CH3
This compound conatins two functional groups (–COOH group and –OH group).
The –COOH group is the principal functional group, i.e. hexanoic acid.
The –OH group attached to the third carbon atom takes the prefix hydroxy. A methyl group
is attached to the fifth carbon atom, i.e. 3-hydroxy-5-methylhexanoic acid.
54 B Option B — H H O
3 2 1
H C C C OH
H NH2
This compound contains two functional groups (–COOH group and –NH2 group).
The –COOH group is the principal functional group, i.e. propanoic acid.
The –NH 2 group attached to the second carbon atom takes the prefix amino, i.e.

2-aminopropanoic acid.
10
O
55 D Option D — This compound contains two functional groups (–COO– group and C group).
The –COO– group is the principal functional group. Thus, the compound is regarded as an
ester.
O CH3
4 3 2 1
H C CH2 C COO CH3
CH3

butanoic acid from methanol
Consider the part coming from butanoic acid. The –CO– group attached to the fourth carbon
atom takes the prefix oxo. Two methyl groups are attached to the second carbon atom.
Thus, the IUPAC name of the compound is methyl 2,2-dimethyl-4-oxobutanoate.
56 C Option C — The boiling point of a compound depends on the strength of its intermolecular
attractions.
Compared with other molecules, molecules of CH3(CH2)6CH3 are the longest and somewhat
spread-out in shape. This allows the greatest surface contact between the molecules.
The van der Waals’ forces in CH3(CH2)6CH3 are thus the strongest. Hence it has the highest
boiling point.
57 D Option D — Among the four compounds, CH4 has the smallest number of electrons in each molecule.
Hence the van der Waals’ forces between its molecules are the weakest. Thus, CH4 is the
most volatile.
58 C Options A, B and D — Hydrogen bonding exists in butan-1-ol, butan-2-ol and butanoic acid, but NOT
in butanal.
The following diagram shows the hydrogen bonding between butan-1-ol molecules:
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Thus, the boiling points of butan-1-ol, butan-2-ol and butanoic acid are higher
than that of butanal.
11
Option C — Butanal is polar. There are permanent dipole-permanent dipole attractions between its
molecules.
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δ+ δ– δ+ δ– δ+ δ–
$ 0 $ 0 $ 0
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LFZ
QFSNBOFOUEJQPMFQFSNBOFOU
EJQPMFBUUSBDUJPO
Only instantaneous dipole-induced dipole attractions exist between but-1-ene molecules.

Compared with permanent dipole-permanent dipole attractions, instantaneous dipole-induced
dipole attractions are less strong. Thus, the boiling point of but-1-ene is lower than that of
butanal.
59 C Option C — Hydrogen bonding exists in octan-1-ol but NOT in the other compounds. Thus, the boiling
point of octan-1-ol is the highest.
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Octan-2-one is polar. There are permanent dipole-permanent dipole attractions between its
molecules.
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δ+ δ– δ+ δ– δ+ δ–
$ 0 $ 0 $ 0
$) $) $)
LFZ
QFSNBOFOUEJQPMFQFSNBOFOU
EJQPMFBUUSBDUJPO
Only instantaneous dipole-induced dipole attractions exist in butane and octane.
Permanent dipole-permanent dipole attractions are stronger than instantaneous dipole-induced
dipole attractions. Thus, the boiling point of octan-2-one is higher than those of octane and
butane.
The strength of instantaneous dipole-induced dipole attractions increases as the length of
the carbon chain in molecules increases. Thus, the boiling point of octane is higher than
that of butane.
The order of boiling point of the four compounds is:
octan-1-ol > octan-2-one > octane > butane.
12
60 C Option C — Due to the hydrogen bonding between ethanol molecules and water molecules, ethanol is
miscible with water in all proportions.
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Alcohols with a long carbon chain in their molecules are much less soluble in water. This is
because these alcohols resemble alkanes more than they resemble water. Thus, the water
solubility of hexan-1-ol is lower than that of butan-1-ol.
The order of water solubility of the three compounds is:
hexan-1-ol < butan-1-ol < ethanol.
61 D Option D — There is NO hydrogen atom attached to the oxygen atom in CH3OCH3. Thus, CH3OCH3
molecules CANNOT form hydrogen bonds with each other.
62 A Option A — The polar CH3CH2CH2F molecules can interact with water molecules, but the attractive
forces set up are not as strong as the hydrogen bonds between water molecules. Hence
CH3CH2CH2F is only slightly soluble in water.
Options B, C and D — CH3CH2CH2NH2, CH3CH2CH2OH and CH3CH2CH2COOH can form hydrogen bonds
with water. Thus, they are quite soluble in water.
63 C (1) Amines contains the –NH2 functional group.
(2) Amides contain the C NH2 functional group.
(3) Esters contain the C O functional group.
64 B (2) Ethene (C2H4) and cyclohexane (C6H12) have the same empirical formula (CH2).
65 B (1) The functional group in CH3CH2OCH2CH3 is the –O– group while that in CH3CH(OH)CH2CH3 is the
–OH group. Thus, they belong to different homologous series.
(2) Both HCOOCH2CH2CH3 and CH3COOCH2CH3 are esters.
(3) CH3CH2COOH is a carboxylic acid while CH3COOCH3 is an ester.
13
66 C (1) and (3) This compound contains a carbon-carbon double bond and a carbonyl group.
O
carbonyl group
CH3CH CHCH2CCH3
carbon-carbon
double bond
67 A (1) This compound contains an amide functional group.
CH3CONH OH
amide functional group
68 B (1) and (2) OH
NH2
This compound contains two functional groups: –OH group and –NH2 group.
The –OH group is the principal functional group. Thus, the compound should be regarded
as an alcohol, NOT an amine.
69 B (1) There is NO hydrogen atom attached to the fluorine atom in CH2F2. Thus, hydrogen bond does
NOT exist in CH2F2.
70 D CH3COCH2CH3 is a ketone while CH3CH2CH2CHO is an aldehyde.

(1) The two compounds belong to different homologous series.
( )
O
(2) Both compounds contain a carbonyl group C .

(3) Molecules of both can form hydrogen bonds with water molecules.
The following diagram shows the hydrogen bonding between molecules of CH3COCH2CH3 /
CH3CH2CH2CHO and water:
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0 0 0
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) ) ) )
0 0 0
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14
71 B Each 1-bromobutane molecule contains more electrons than each 1-chlorobutane. The van der Waals’
forces in 1-bromobutane are stronger than those in 1-chlorobutane.
72 D The intermolecular attractions in propan-1-ol are stronger than those in ethanol. Thus, propan-1-ol is less
volatile than ethanol.
The volatility of members of a homologous series decreases with increasing relative molecular mass.
73 C Propanone is miscible with water because it can form hydrogen bonds with water.
) ) ) )
0 0 0
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)$ $) IZESPHFOCPOE

74 B Hydrogen bonding exists in butan-1-ol, but NOT in butanone. Thus, the boiling point of butan-1-ol is
higher than that of butanone.
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75 A The following diagram shows the hydrogen bonding between a methyl methanoate molecule and a water
molecule:
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IZESPHFOCPOE
76 D Since oxygen is more electronegative than nitrogen, the O–H bond in ethanol is more polar than the N–H
bond in ethanamine. As a result, stronger hydrogen bonds exist between ethanol molecules. This explains
why the boiling point of ethanol is higher than that of ethanamine.
15
Unit 30 Isomerism
Fill in the blanks

1 structural
2 stereoisomers
3 Enantiomers
4 chiral
5 opposite; optically active
True or false
6 T Chain isomers are isomers that have the same functional groups but different carbon skeletons.
Pentane and 2,2-dimethylpropane are chain isomers.
In pentane, the carbon atoms lie in a straight line. In 2,2-dimethylpropane, the chain is branched.
7 F Position isomers belong to the same homologous series. Thus, propanal and propanone are NOT position
isomers.
8 F The melting point of a substance depends on intermolecular attractions as well as molecular symmetry.
In both cis-but-2-ene and trans-but-2-ene, the intermolecular attractions are van der Waals’ forces and
they are of comparable strength.
CH3 CH3 CH3 H
C C C C
H H H CH3
cis-but-2-ene trans-but-2-ene
The trans isomer has a more regular and symmetrical structure than the cis isomer. Molecules of the trans
isomer can pack more compactly in the solid. More heat is required to overcome the intermolecular forces
between the molecules. Hence the trans isomer has a higher melting point than the cis isomer.
9 T Cis-butenedioic acid has a net dipole moment.
H COOH
C net
dipole
C moment
H COOH
cis-butenedioic acid
16
10 T Only 2-nitrophenol can form intramolecular hydrogen bond.
N
O
IZESPHFOCPOE
H
O
It forms less intermolecular hydrogen bonds than 4-nitrophenol. Hence 2-nitrophenol is more volatile than
4-nitrophenol.
11 F The boiling point of cis-1,2-dichloroethene is higher than that of trans-1,2-dichloroethene.

In a molecule of the cis isomer, both –Cl groups are on the same side of the carbon-carbon double bond.
The molecule has a net dipole moment and it is polar. These molecules are held together by permanent
dipole-permanent dipole attractions.
δ–
Cl Clδ– δ–
Cl H
net no
dipole δ+ δ+ net
δ+
C C δ+
C C
moment dipole
moment
δ–
H H H Cl

In a molecule of the trans isomers, the bond dipole moments cancel one another out and there is no
net dipole moment. These molecules are held together by instantaneous dipole-induced dipole attractions.
Less heat is required to separate the molecules during boiling.
12 T In a butan-2-ol molecule, four different groups are attached to the second carbon atom. The molecule
is chiral.
H
1 2 3 4
CH3 C CH2CH3
OH
chiral carbon
13 F Molecule of 3-bromohexane does NOT have a plane of symmetry.
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17
14 T A pair of enantiomers have the same physical properties.
15 F A pair of enantiomers have the same chemical properties, except their reactions with chiral reagents.
16 B Option B — C4H9OH and C2H5OC2H5 are different compounds that have the same molecular formula
(C4H10O). They are isomers.
17 D Option D — Position isomers are isomers that have the same carbon skeleton and functional group. They
differ only in the position of the functional group.
OO OO O O
18 B Option B — CH
CH3CCH
3CCH2CH2CH
2CH2CH3 3 and CH3CH
CH 2CH
3CH 2CH
2CH2CH 2CHhave the same molecular
2CH CH3CCHformula
2CH2CH3 (C 5H 10O) but C
O belong
O to different homologous series.
OO OO O O
CH3CCH2CH2CH3 C
CH3CCH
CH 2CH
3CCH 2CH
2CH 3 3 contains a
2CH CC functional group while CH3CH2CH2CH2CH contains a C H
O O
OO OO
CH3CH 2CH2 CH2 CH C H functional group.
CH3CH
CH 2CH
3CH 2CH
2CH2CH2CH
2CH CC HH
19 B Option B — There are 3 structural isomers with the molecular formula C5H12.
H H H H H H H CH3 H H CH3 H
H C C C C C H H C C C C H H C C C H
H H H H H H H H H H CH3 H
20 C Option C — Three isomers exist for dibromobenzene.

Br Br Br
Br
Br
Br
21 D Option D — Four structurally isomeric alcohols have the formula C4H9OH.
H H H H H H OH H
H C C C C OH H C C C C H
H H H H H H H H
H CH3 H H CH3 H
H C C C OH H C C C H
18 H H H H OH H
22 A Option A — Two different compounds have the molecular formula C2H3Cl3.
H Cl H H
H C C Cl H C C Cl
H CI Cl Cl
23 D Option D — There are 4 structural isomers with the molecular formula C3H6Cl2.
H H Cl H Cl Cl
H C C C Cl H C C C H
H H H H H H
Cl H Cl H Cl H
H C C C H H C C C H
H H H H Cl H
24 C Option C — There are 4 structural isomers with the molecular formula C2HBrClF3.
F H F F F F
F C C Br F C C Br H C C F
F Cl H Cl Br Cl
haloethane
F F
H C C F
Cl Br
25 B Option A — The two compounds are amines, NOT amides.

Option B — The two compounds have the same carbon skeleton and functional group (–NH2), but differ
in the position of the functional group. Thus, they are position isomers.
Option C — The two compounds are soluble in water because they can form hydrogen bonds with
water.
Option D — The boiling point of X is lower than that of Y.
The boiling point of a compound depends on the strength of its intermolecular
attractions.
Compared with Y, the shape of molecule of X is more spherical and compact, thus there is
less surface contact between molecules. Hence the van der Waals’ forces in X are weaker.
19
26 C Option A — Butane has 2 structural isomers.
Options B and D — Ethane and propane have NO isomer.
Option C — Pentane has 3 structural isomers.
27 B Option B — The two molecules are geometrical isomers.
C3H7 H C3H7 CH3

C C C C
H CH3 H H
28 C Option C — Compounds with two different groups attached to each carbon of the double bond have
two different structures, which are geometrical isomers.
CHBr=CHCl can exhibit geometrical isomerism.
H H H CI
C C C C
Br CI Br H
cis isomer trans isomer
29 C Compounds with two different groups attached to each carbon of the double bond have two different
structures, which are geometrical isomers.
Option A — This compound has two identical ethyl groups attached to one of the carbon atoms of the
double bond. Thus, it CANNOT exhibit geometrical isomerism.
CH3
CH3CH2C CCH2CH3
C2H5
ethyl groups
H H
Option C — C2H5C CCH2I can exhibit geometrical isomerism.
H H H CH2I
C C C C
C2H5 CH2I C2H5 H
cis isomer
trans isomer
20
30 D Option D — Six geometrical isomers are possible for the compound with molecular formula C2HBrClF.
H Cl H F
C C C C
Br F Br Cl
H Br H F
C C C C
Cl F Cl Br
H Cl H Br
C C C C
F Br F Cl
31 B Option B — In a molecule of this compound, four different groups are attached to the second carbon
atom. The molecule is chiral.
H H H H
4 3 2 1
H C C C C H
H H Cl H
chiral carbon
32 A Option A — In a molecule of CH3CH(NH2)COOH, four different groups are attached to the second carbon
atom. The molecule is chiral. The compound exists as a pair of enantiomers.
H H
C COOH HOOC C
CH3 CH3
NH2 H2N
NJSSPS
33 B Option B — The carbon atom numbered ‘2’ has four different groups attached to it. It is chiral.
H
2
HOCH2 C CH2NHC(CH3)3
OH
HO
chiral carbon

21
34 B Option B — The molecule contains 1 chiral carbon.
CH3CH2CH(CH3)CH CH2
chiral carbon
35 B Option B — Warfarin contains 1 chiral carbon.
chiral carbon
O
O
C
C
C CH CH2 C CH3
OH O
36 B Option B — 1,3-dichlorobutane is a chiral molecule.
H CI H Cl
H C C C C H
H H H H
chiral carbon

37 B Option B — The compound contains 1 chiral carbon. Thus, it has a pair of enantiomers.
O
CH2OH
chiral carbon
38 A Option A — The mirror image of the first molecule is shown below:
COOH COOH
GJSTUNPMFDVMF
C C
NH2 NH2
H H
CH3 CH3
NJSSPS
The first molecule and its mirror image are not superposable.
22
Rotating the mirror image produces the second molecule.
NH2 NH2
COOH
C C
C H COOH
NH2 CH3 H
H
COOH CH3
CH3
TFDPOENPMFDVMF
Thus, the two molecules are non-superposable mirror images of each other; i.e. they are
enantiomers.
39 D Option D — Rotating the first molecule about the C–Cl bond produces the second molecule.
CH3 Cl
C C
Cl H
(CH3)3C (CH3)3C
H CH3

Thus, the two molecules are identical.
40 B Option A — The two members are geometrical isomers.

Option B — The mirror image of the first molecule is shown below:
Br Br
GJSTUNPMFDVMF
C C
CH3 CH3
CH2=CH CH=CH2
H H
NJSSPS
Br H H
C C
C Br CH3
CH3 CH2=CH
CH3 CH=CH2
H Br
CH=CH2
TFDPOENPMFDVMF
Thus, the two molecules are non-superposable mirror images of each other; i.e. they are
enantiomers. 23
Option C — Rotating the first molecule produces the second molecule.
Cl H
C C
CH3 CH3
H3C H3C
H Cl
C
Cl
H3C
CH3
Option D — The two molecules are identical.
41 C Option A — Rotating the first molecule about the C–CH3 bond produces the second molecule.
CH3 CH3
C C
Br H
H F
F Br
HH33CC Br
Br HH33CC FF
CC CC CC CC
Option B — HH33CC FF and HH33CC Br are identical molecules.
Br
Option C — The second molecule is the mirror image of the first molecule.
CH3 CH3
GJSTUNPMFDVMF TFDPOENPMFDVMF
C C
H Br Br H
F F
NJSSPS
The two molecules are non-superposable mirror images, NOT identical molecules.
24
42 C Option A — 2-chloropropane has a plane of symmetry. It CANNOT exhibit enantiomerism.
QMBOFPGTZNNFUSZ
$*
$ $)
$)
)

Option B — 2-methylbut-1-ene has two hydrogen atoms attached to one carbon of the double bond.
Thus, it CANNOT exhibit geometrical isomerism.
CH3 H
C C
C2H5 H
Option C — 2-methylbutanoic acid contains 1 chiral carbon. It can exhibit enantiomerism.
H H CH3 O
H C C C C OH
H H H
chiral carbon
Option D — 3-methylbutan-1-ol does NOT contain any chiral carbon. It CANNOT exhibit
enantiomerism.
H CH3 H H
H C C C C OH
H H H H
43 B Options A, C and D — Each of these compounds has two identical groups attached to one carbon of
the double bond. Thus, they would NOT have geometrical isomers.
Option B — CH3CH2CH=CHCH(CH3)CH2CH3 has two different groups attached to each carbon of the
double bond. Thus, it has geometrical isomers.
This compound has four different groups attached to the carbon marked. It is chiral. Thus,
it has enantiomers.
CH3CH2CH CHCH(CH3)CH2CH3
chiral carbon
25
44 A Option A — Both have the same molecular formula (C10H20O).
Option B — Both have a hydroxyl functional group, NOT carboxyl functional group.
Option C — X contains a chiral carbon but Y does NOT.
OH H H H H
H C C C C C
CH3
C C
H H CH3 H H CH3
H
chiral carbon
Option D — Y has two different groups attached to each carbon of the double bond. Thus, it can exhibit
geometrical isomerism.
X has two methyl groups attached to one carbon of the double bond. Thus, it CANNOT
exhibit geometrical isomerism.
( )
Br Br
C C
45 A Option A — C2Br4 Br Br could NOT exist in isomeric forms.
46 D
47 B Option B — Atenolol contains 1 chiral carbon.
H2NCOCH2 OCH2CH(OH)CH2NHCH(CH3)2
chiral carbon
48 B (1) and (3) An atenolol molecule contains an amine functional group and a hydroxyl group.
H2NCOCH2 OCH2CH(OH)CH2NHCH(CH3)2
hydroxyl group amine functional group
49 C X contains a –OH group while Y contains a –O– group. They belong to different homologous series.
(1) and (2) Chain isomers are isomers that have the same functional groups but different carbon
skeletons. Thus, X and Y are NOT chain isomers.
(3) Hydrogen bonding exists in X but NOT in Y. Thus, the boiling point of X is higher than that of Y.
50 D (1) Halothane has a chiral carbon.

H F
CI C C F
Br F
26 chiral carbon
H F
(2) Halothane has structural isomers, e.g. F C C F.
Br CI
51 B (2)
MFGU SJHIU "MFGUTIPFBOEJUTNJSSPSJNBHF JFBSJHIUTIPF

BSFOPUTVQFSQPTBCMF5IVT BTIPFJTDIJSBM
52 A (1) H CH3
2
1
O
3

4 6
5
A methyl group is attached to the second carbon atom of the cyclohexanone, i.e.
2-methylcyclohexanone.
(2) This compound contains 1 chiral carbon.
chiral carbon
H CH3
O
53 B (1) 2,4-dimethylheptane contains 1 chiral carbon.
H H H CH3 H CH3 H
H C C C C C C C H
H H H H H H H
chiral carbon

27
QMBOFPGTZNNFUSZ
chiral carbon
(2) 5-ethyl-3,3-dimethylheptane has a plane of symmetry. Thus, it is achiral.
QMBOFPGTZNNFUSZ
$) $)
QMBOFPGTZNNFUSZ
$
$) $) $)
)
$ )
$
$)
)
$ $ )
$)
) $)
$
$)
) $)

(3) 2-hydroxypropanoic acid contains 1 chiral carbon.
H OH O
H C C C OH
H OH O
H H
H C C C OH
chiral carbon
H H
54 A (1) Rotating the second
chiralmolecule
carbon about the C–CH3 bond produces the first molecule.
CH3 CH3
CH3 CH3
C C
Cl C2H5
HC H C
Cl C2H5
C2H5 H HCl
C2H5 Cl
(2) The mirror image of the first molecule is shown below:
H H
GJSTUNPMFDVMF
H H
GJSTUNPMFDVMF
C C
Cl Cl
HOOC C COOH
C
Cl Cl
CH3
HOOC CH3 COOH
CH3 NJSSPS CH3
NJSSPS

H H
H H
28
C C
Cl CH3
COOH
C HOOC C
Cl CH3
Cl Cl
HOOC COOH
HOOC COOH
CH CH
CH3 3 CH3 3
NJSSPS
NJSSPS
Rotating the mirror image about the C–H bond produces the second molecule.
H H
H H
C C
Cl C C CH
Cl COOH HOOC CH3 3
COOH HOOC
CH Cl
CH3 3 Cl

Thus, the two molecules are enantiomers, NOT identical.
(3) The two molecules are geometrical isomers, NOT identical.
H H H Br
H H H Br
C C C C
C C C C
Br Br Br H
Br Br Br H
55 B (2) This compound contains 1 chiral carbon. It can exhibit enantiomerism.
H H O
H C C C OH
H OH
chiral carbon
56 B (2) C2H5CHCl2 has a plane of symmetry.
QMBOFPGTZNNFUSZ
$)
$* $ chiral carbon
$*
chiral carbon )
CH3
H3C CHCICH3
C C
H H
57 C (1) This compound has a plane of symmetry. It is optically inactive.
CH3
QMBOFPGTZNNFUSZ

29
(2) and (3) Both compounds have 1 chiral carbon. They are optically active.
chiral carbon
chiral carbon
CH3
H3C CHCICH3
C C
H H
58 C (2) This compound contains 1 chiral carbon. It can exist in optically active forms.
CH3
chiral carbon
chiral carbon
CH3CH2CHCH2 C N
QMBOFPGTZNNFUSZ
CH3CH2CHCH2 C N
CH3
CH3
(3) This compound has a permanent dipole.
CH3CH2CHCH2 C N
CH3CH2CHCH2 C N
CH3 net
CH3 net
dipole
dipole
moment
moment
59 B (1) The compound has two hydrogen atoms attached to one carbon of the double bond. Thus, it is
NOT a cis or trans isomer.
O

H C OCH3
C C
(2) The compound has structural isomers, e.g. H3C H
(3) The compound has NO chiral carbon.
60 B (1) The double bond of compound X exists between the third and fourth carbon atoms. Thus, its
systematic name is hex-3-en-1-ol.
6 5 4 3 2 1
CH3CH2CH=CHCH2CH2OH
(2) Compound X has geometrical isomers.
H H H CH2CH2OH
C C C C
CH3CH2 CH2CH2OH CH3CH2 H
(3) Compound X contains NO chiral carbon. It does NOT have enantiomers.
30
61 A (1) Compound X has a carbonyl (–CHO) group.
(2) Compound X has 1 chiral carbon.
CH3
chiral carbon CH
CH2 CH2
CH2 CHO
CH2
CH3 CH2
(3) Compound X has two hydrogen atoms attached to one carbon of the double bond. Thus, it
CANNOT exhibit geometrical isomerism.
62 A (1) The –COOH group is the principal functional group. Thus, this compound is regarded as a
carboxylic acid, i.e. butanoic acid.
The –OH group is attached to the third carbon atom, i.e. 3-hydroxybutanoic acid.
4 3 2 1
CH3CH(OH)CH2COOH
(2) The compound contains 1 chiral carbon. Thus, it is optically active.
CH3CH(OH)CH2COOH
chiral carbon
63 C (2) Two compounds of molecular formula C2H2Cl2 could be related as geometrical isomers.
H CI H H
C C C C
CI H CI CI
(3) Two compounds of molecular formula C2H2Cl2 could be related as structural isomers.
H2C=CCl2 ClHC=CHCl
31
64 B (1) The two compounds are position isomers.
(3) In a molecule of X, due to the close proximity of the –OH group and –CHO group, intramolecular
hydrogen bonds are readily formed. Thus, intermolecular hydrogen bonds between the molecules
of X are less extensive.
O
H
IZESPHFOCPOE
O
C
Molecules of Y form more intermolecular hydrogen bonds than molecules of X do.

Thus, the melting point of Y is much higher than that of X.
65 C (1) Compounds X and Y are geometrical isomers.
CH3OOC H H H
C C C C
H COOCH3 CH3OOC COOCH3
trans isomer cis isomer
(3) The melting point of a substance depends on intermolecular attractions as well as molecular
symmetry.
In both compounds, the intermolecular attractions are van der Waals’ forces and they are of
comparable strength.
Compound X (the trans isomer) has a more regular and symmetrical structure than compound Y
(the cis isomer). Molecules of compound X can pack more compactly in the solid. More heat is
required to overcome the intermolecular forces between the molecules. Hence compound X has
a higher melting point than compound Y.
66 D (1) and (2) A pair of enantiomers have the same physical property, except their behaviour towards plane-
polarized light.
δ–
67 C (1)
δ–
δ– Cl
Cl H
H
Cl H
net
net
δ+
δ+ C C net
dipole
δ+ C C dipole
dipole
C C moment
moment
δ–
moment
δ–
δ– Cl
Cl H
H
Cl H
δ–
Cl
δ–
Cl H
H
(2) δ–
Cl H no
no
no
net
δ+
δ+ C C δ+
δ+ net
δ+ C C δ+ net
dipole
C C dipole
dipole
moment
moment
moment
H
H Clδ–δ–
Cl
H Clδ–
δ–
(3) Cl
δ–
Cl
δ– Clδ–δ–
Cl
Cl Clδ–
net
net
δ+ δ+ net
dipole
δ+ C
C Cδ+
C dipole
δ+
C Cδ+ dipole
moment
moment
moment
32 H
H H
H
H H
68 B (2) The mirror image of the first molecule is shown below:
CH3 CH3
CH3 CH3
C C
NH2 H2N
H C C H
NH2 H2N
H H
COOH COOH
COOH COOH
NJSSPS
NJSSPS
Rotating the mirror image about the C–CH3 bond produces the second molecule.
CH3 CH3
CH3 CH3
C C
H H COOH
H2N C C
H H COOH
H2N
NH2
COOH
NH2
COOH

Thus, the two compounds are enantiomers. They rotate the plane of polarized light in opposite
directions.
(3) A pair of enantiomers have the same physical property, except their behaviour towards plane-
polarized light.
Thus, the two compounds have the same melting point.
69 D Chain isomers are isomers that have the same functional groups but different carbon skeletons.
Propanoic acid and methyl ethanoate have different functional groups. They are NOT chain isomers.
Propanoic acid (CH3CH2COOH) and methyl ethanoate (CH3COOCH3) have the same molecular formula
(C3H6O2).
70 A
( )
H Cl
H C C Cl
71 D 1,1-dichloroethane molecule H H does NOT contain any carbon atom bonded to four
different atoms.
( )
H Cl H
H C C C H
72 D 2-chloropropane H H H does NOT have any chiral carbon.

33
73 C Butan-1-ol and butan-2-ol have different boiling points.
The boiling point of a compound depends on the strength of its intermolecular attractions.
The hydrogen bonds in butan-1-ol and butan-2-ol are of comparable strength.
Compared with butan-2-ol molecules, butan-1-ol molecules are longer and somewhat spread-out in shape.
This allows greater surface contact between the molecules.
The van der Waals’ forces in butan-1-ol are thus stronger. Hence it has a higher boiling point (the boiling
point of butan-1-ol is 118 °C while that of butan-2-ol is 100 °C).
74 C The melting point of cis-1,2-dichloroethene is lower than that of trans-1,2-dichloroethene.
Cl Cl Cl H
C C C C
H H H Cl
cis-1,2-dichloroethene trans-1,2-dichloroethene
The melting point of a compound depends on intermolecular attractions as well as molecular symmetry.
The cis isomer has a lower degree of symmetry. It fits into a crystalline lattice relatively poor and thus
has a lower melting point.
Cis-1,2-dichloroethene has a net dipole moment while trans-1,2-dichloroethene has not.
δ–
Cl Clδ– δ–
Cl H
net no
dipole δ+ δ+ net
δ+
C δ+
C C C
moment dipole
moment
H H H Clδ–
Unit 31 Typical reactions of selected functional groups
Fill in the blanks

1 addition / hydrogenation
2 substitution / hydrolysis
3 substitution
4 dehydration / elimination
5 oxidation
6 reduction
7 esterification / condensation
8 hydrolysis
34
True or false
9 T Methylpropan-2-ol has three alkyl groups attached to the carbon bearing the –OH group. Thus, it is a
tertiary alcohol.
CH3
H3C C CH3
OH
10 F 1-iodopropane is obtained when propan-1-ol reacts with hydrogen iodide.

However, when concentrated sulphuric acid reacts with sodium iodide, the acid oxidizes the iodide ions
to iodine and produces very little hydrogen iodide.
Thus, concentrated phosphorus acid should be used instead.
11 F Propan-2-ol is oxidized to propanone, NOT propanoic acid.
H H H H O H
[O]
H C C C H H C C C H
H OH H H H
propan-2-ol propanone
12 F Lithium aluminium hydride can reduce butanal to butan-1-ol.
O OH
1 LiAlH4 / ethoxyethane
CH3CH2CH2CH CH3CH2CH2CH
2 H3O+
butanal
H
butan-1-ol
13 T Butan-1-ol can turn the orange acidified potassium dichromate solution green, but butanone CANNOT.
14 T Hydrolysis of methyl ethanoate produces methanol and ethanoic acid.
O O
hydrolysis
CH3 C O CH3 CH3 C OH + CH3 OH

15 T
35
16 C Option A — The reaction involves substitution of hydrogen with bromine. Sufficient energy (e.g. from
ultraviolet light) must be supplied for the reaction to proceed. Thus, the reaction does NOT
occur in the dark.
Option D — The product ( CH2Br )

does NOT contain a carbon atom with four different groups
attached to it. Thus, the product is optically INACTIVE.
17 C Option C — Structures of the two different monochloropropanes formed are shown below:
H H H H Cl H
H C C C Cl H C C C H
H H H H H H
These two monochloropropanes are NOT geometrical isomers.
18 B Option B — Propane is formed in this addition reaction.

H3C H
H3C H H2 / Pt catalyst
C C H C C H
H H
H H
propane
19 D Option D — Pent-2-ene undergoes an addition at the double bond with chlorine. Thus, two Cl atoms
are added to the adjacent carbon atoms of the double bond. 2,3-dichloropentane is
produced.
Cl Cl
Cl2
CH3CH2CH CHCH3 CH3CH2CHCHCH3
pent-2-ene 2,3-dichloropentane
20 D Option D — Propene undergoes an addition at the double bond with aqueous bromine. Thus, two Br
atoms / one Br atom and one OH group are added to the adjacent carbon atoms of the
double bond.
Br Br Br OH OHBr
Br2(aq)
CH3CH CH2 CH3CHCH2 + CH3CHCH2 + CH3CHCH2
propene 1,2-dibromopropane
1,3-dibromopropane is NOT produced in the reaction between propene and aqueous

bromine.
36
21 C Option C — Cyclohexene undergoes an addition at the double bond with aqueous bromine. Thus, two
Br atoms / one Br atom and one OH group are added to the adjacent carbon atoms of the
double bond.
Br Br
Br2(aq)
+
Br OH
22 C Option C — When a molecule HA adds to an asymmetric alkene, the major product is the one in which
the hydrogen atom attaches itself to the carbon atom already carrying the larger number
of hydrogen atoms.
Br H H Br
H3C HBr(g)
C CH2 H3C C C H + H3C C C H
H3C
CH3 H CH3 H
this carbon atom major product minor product
carries more
hydrogen atoms
23 A Option A — When a molecule HA adds to an asymmetric alkene, the major product is the one in which
of hydrogen atoms.
Br H H Br
H5C2 C2H5 HBr(g)
C C C2H5 C C C2H5 + C2H5 C C C2H5
H3C H
CH3 H CH3 H
carries more 3-bromo-3-methylhexane
hydrogen atoms
24 C Hydrocarbon X decolorizes aqueous bromine in the dark. It should be unsaturated.

Option A — C2H6 is a saturated hydrocarbon.
Option B — C3H6 is a gaseous hydrocarbon.
Option C — C6H12 is a liquid hydrocarbon. C6H12 with an acyclic structure is unsaturated.
Option D — C8H18 is a saturated hydrocarbon.
25 B Option B — The piece of apparatus labelled X is a reflux condenser.
26 D Option D — In the reflux condenser, all the vapour is condensed back into the flask. This prevents any
loss of the reaction mixture.
27 B Options B and C — Substitution reaction of 1-bromobutane takes place in the experiment.
CH3CH2CH2CH2Br + OH– CH3CH2CH2CH2OH + Br–

butan-1-ol
Option D — The C–F bond is so strong that 1-fluorobutane is extremely unreactive. 37
28 C Option A — 2-bromobutane contains a carbon atom with four different groups attached to it. Thus, it
is optically active.
H H Br H
H C C C C H
H H H H
chiral carbon
Option B — Position isomers are isomers that have the same carbon skeleton and functional group. They
differ only in the position of the functional group.
2-bromobutane and 1-bromobutane are position isomers.
H H Br H H H H Br
H C C C C H H C C C C H
H H H H H H H H
2-bromobutane 1-bromobutane
Option C — The polar 2-bromobutane molecules can interact with water molecules, but the attractive
forces set up are not as strong as the hydrogen bonds between water molecules. Hence
2-bromobutane is only slightly soluble in water.
Option D — hydrolysis
CH3CH2CHBrCH3 CH3CH2CH(OH)CH3
2-bromobutane butan-2-ol
29 C Option C — The classification of alcohols is based on the number of alkyl groups attached to the carbon
bearing the –OH group.
H CH3
H3C C OH H3C C OH
H H
one alkyl group two alkyl groups

attached to this carbon, attached to this carbon,
i.e. primary alcohol i.e. secondary alcohol
CH3
H3C C OH
CH3
three alkyl groups

attached to this carbon,
i.e. tertiary alcohol

38
30 D Option D — Substitution reaction occurs when concentrated hydrochloric acid is heated under reflux with
ethanol in the presence of zinc chloride.
31 A
32 A Option A — The major organic product is chloroethane.

reflux
CH3CH2OH + HCl CH3CH2Cl + H2O
ZnCl2 catalyst
ethanol chloroethane
33 D Options A, B and C — SOCl2, PCl5 and HCl will convert butan-1-ol to 1-chlorobutane in one step.
CH3CH2CH2CH2OH CH3CH2CH2CH2Cl
butan-1-ol 1-chlorobutane
CH3
CH3
H3C C CH3
H3C C CH3
34 C Option A — OH is a tertiary alcohol. It reacts rapidly with concentrated hydrochloric acid
without OH
a catalyst.
Option B — The major organic product is 2-chloro-2-methylpropane, NOT 1-chloro-2-methylpropane.
CH3 CH3
CH3 conc. HCl CH3
H3C C CH3 H3C C CH3
conc. HCl
H3C C CH3 H3C C CH3
OH Cl
OH Cl
2-chloro-2-methylpropane
2-chloro-2-methylpropane
Option D — The order of reactivity of alcohols in substitution reactions with halides is 3° > 2° > 1°.
Thus, a slower reaction will occur if butan-1-ol is used instead.
35 C Option C — Concentrated sulphuric acid reacts with sodium bromide to produce hydrogen bromide.
NaBr + H2SO4 NaHSO4 + HBr
36 B
37 C
38 B Option B — Organic product A is 2-bromobutane.
CH3CH2CH(OH)CH3 + HBr CH3CH2CHBrCH3 + H2O
butan-2-ol 2-bromobutane
39
39 C Option C — To prepare iodoethane, ethanol is reacted with a mixture of sodium iodide and concentrated
phosphoric acid. Concentrated phosphoric acid reacts with sodium iodide to produce hydrogen
iodide, which reacts with ethanol.
reflux
CH3CH2OH + HI CH3CH2I + H2O
ethanol iodoethane
Option D — When concentrated sulphuric acid reacts with sodium iodide, the acid oxidizes the iodide
ions to iodine and produces very little hydrogen iodide. Thus, concentrated sulphuric acid is
NOT used.
40 A Option A — To prepare a bromoalkane, the alcohol is heated under reflux in a water bath with a
mixture of red phosphorus and bromine. Phosphorus first reacts with bromine to give
phosphorus tribromide. The tribromide then reacts with the alcohol to give the corresponding
bromoalkane.
2P + 3Br2 2PBr3
41 B Option B — The organic product formed is 1-bromo-2-methylpropane.

3CH3CH(CH3)CH2OH + PBr3 3CH3CH(CH3)CH2Br + H3PO3
1-bromo-2-methylpropane
42 C
43 A
44 D Option D — Ethanol undergoes dehydration in the experiment. Ethene is produced.

CH3CH2OH C2H4 + H2O
45 A Option A — Ethanol is a primary alcohol. It is difficult to dehydrate. Concentrated sulphuric acid, NOT
20% H2SO4, needs to be used in the experiment.
46 D Option D — Alcohol X undergoes dehydration.

CH3
20% H2SO4 H3C H
CH3 C CH3 C C
85 oC H3C H
OH methylpropene
alcohol X
47 C Option B — Alcohol X does NOT contain any carbon atom with four different groups attached to it.
Thus, it has NO chiral centre.
Option D — The relative ease with which alcohols undergo dehydration shows the following order:
Ease of dehydration: 3° > 2° > 1° alcohol
Alcohol X is a tertiary alcohol while butan-1-ol is primary alcohol. Thus, a slower reaction
will occur if butan-1-ol is used instead.
40
48 A
49 C Option C — Dehydration of the alcohol gives two alkenes.
H H H
dehydration
H C C C CH2CH3 CH2 CHCH2CH2CH3
minor product
H OH H
remove
H H H
dehydration
H C C C CH2CH3 CH3CH CHCH2CH3
major product
H OH H
remove
CH3CH=CHCH2CH3 has two alkyl groups attached to the carbon atoms of the C=C bond
while CH2=CHCH2CH2CH3 has one. CH3CH=CHCH2CH3 is the more highly substituted alkene
and hence the major product.
50 C
51 D Option D — The reaction mixture is heated in a flask connected to a reflux condenser. In the reflux
condenser, all the vapour is condensed back into the flask. This prevents any loss of the
reaction mixture and favours the oxidation of propan-1-ol to propanoic acid rather than to
propanal.
52 D
53 B Option B — The following ionic half-equation represents the oxidation of ethanol:
CH3CH2OH(l) + H2O(l) CH3COOH(aq) + 4H+(aq) + 4e–......(1)

CH3CH2OH(l) + H2O(l) CH3COOH(aq) + 4H+(aq) + 4e–......(1)
4H+(aq) +of4eCr
–
TheCH 3CH2OH(l)
following ++H2half-equation
ionic O(l) – CH 3COOH(aq)
represents +reduction ......(1)
2–
2Cr (aq) + 7H2O(l)......(2) 2O7 (aq) ions:
the
2– 3+
Cr2O7 (aq) + 14H (eq) + 6e
Cr2O72–(aq) + 14H+(eq) + 6e– 2Cr3+(aq) + 7H O(l)......(2)

Cr2O72–(aq) + 14H+(eq) + 6e– 2Cr3+(aq) + 27H2O(l)......(2)
(i) Combine
x 3 3CH3CH the2OH(l)
two +ionic
3H2O(l) 3CH3COOH(aq)
half-equation to obtain + 12H+(q) + 12e–
the ionic equation.
+
(i) x 3 3CH3CH2OH(l)16 + 3H O(l) 3CH3COOH(aq) 11 + 12H (q)+ + 12e– –
(i) x 3 3CH2–3CH2OH(l) ++ 23H2O(l) – 3CH
3+ 3COOH(aq) + 12H (q) + 12e
(ii) x 2 2Cr2O7 (q) + 28H (aq) + 12e 4Cr (aq) + 14H2O(l)
16 + 11
(ii) x3CH
2 2Cr O 2–
(q) 16 2–+ + 12e– –+
2– + 28H (aq) 4Cr 3+
(aq) 11
3+ + 14H2O(l)
(ii) x 32CH
2
2OH(l)
2Cr7 + 2Cr
2O7 (q) 2O7 (aq) + 12e
+ 28H 16H (aq) 4Cr (aq) + 14H2O(l)
3CH3CH2OH(l) + 2Cr2O72–(aq) 3CH3COOH(aq) + 4Cr3+(aq) + 11H2O(l)
+ 16H+(aq)
3CH3CH2OH(l) + 2Cr2O72–(aq) + 16H+(aq)
3CH3COOH(aq) + 4Cr3+(aq) + 11H2O(l)
3CH3COOH(aq) + 4Cr3+(aq) + 11H2O(l)
∴ the value of W is 2.
41
54 D Option D — Ethanol in the wine is oxidized to ethanoic acid. The acid makes the wine tastes sour.
55 B Option B — Propan-2-ol is oxidized to propanone.
OH O
CH3 C H + [O] CH3 C CH3 + H2O

propanone
CH3
propan-2-ol
56 C Option C — Butan-1-ol is oxidized to butanal. The butanal is distilled off so that it is not further
oxidized.
OH O
CH3CH2CH2 C H + [O] CH3CH2CH2 C H + H2O

butanal
H
butan-1-ol
57 C Option B — Butan-1-ol does NOT contain any carbon atom with four different groups attached to it.
Thus, it has NO chiral centre.
Option C — Orange dichromate ions are reduced to green chromium(III) ions in the reaction.
Option D — Acidified potassium permanganate solution is an oxidizing agent which is too powerful to
stop at butanal. It oxidizes butan-1-ol to butanoic acid.
58 D Option D — Acidified potassium permanganate solution oxidizes propanal to propanoic acid.
O O
CH3CH2 C H + [O] CH3CH2 C OH

propanal propanoic acid
59 B Option A — CH3CH2CHO would NOT give hydrogen chloride fumes with phosphorus pentachloride.
Option B — Phosphorus pentachloride reacted with compound X in the cold. Hydrogen chloride fumes
were produced. This showed the presence of a hydroxyl group in a compound.
CH3CH2CH2OH + PCl5 CH3CH2CH2Cl + POCl3 + HCl

compound X
Acidified potassium dichromate solution oxidized compound X. The orange dichromate ions
were reduced to green chromium(III) ions.
Options C and D — Both CH3CH2COOH and CH3COCH3 would NOT react with acidified potassium
dichromate solution.
42
CH3
CH3CH2 C OH
60 C Option C — CH3 is a tertiary alcohol. It resists the oxidation by acidified potassium

dichromate solution.
61 A Option A — Alcohol X and methylpropan-2-ol are different compounds with the same molecular formula
(C4H10O). They are structural isomers.
CH3CH(OH)CH2CH3 (CH3)3COH
alcohol X CH
CH3CH(OH)CH methylpropan-2-ol
(CH ) COH
2 3 3 3
CH3CH(OH)CH2CH3 (CH3)3COH
alcohol X methylpropan-2-ol
alcohol X methylpropan-2-ol
Option B — Alcohol X contains 1 chiral carbon. It is optically active.
CH3CH(OH)CH2CH3
CH3CH(OH)CH2CH3
CH3CH(OH)CH2CH3
chiral carbon
chiral carbon
Option C — When warmed with acidified potassium dichromate solution, the dichromate solution turns
chiral carbon
from orange to green.
H H of alcohol
Option D — Dehydration H X gives two alkenes.
H H H dehydration
H CH CH CH CH3 CH2 CHC2H5
dehydration
H C C C CH3 dehydration CH2but-1-ene
CHC2H5
H HC OH
C HC CH3 CH CHC H
minor product2 5
2
but-1-ene
H OH H but-1-ene
H OH H minor product
remove minor product
remove
H remove
H H
H H H dehydration
H CH CH CH CH3 CH3CH CHCH3
dehydration
H C C C CH3 dehydration but-2-ene
CH3CH CHCH3
H HC OH
C HC CH3 CH3CH product
major CHCH3
but-2-ene
H OH H but-2-ene
major product
H OH H
remove major product
remove
remove
But-2-ene has two alkyl groups attached to the carbon atoms of the C=C bond while
but-1-ene has one. But-2-ene is the more highly substituted alkene and hence the major
product.
62 C
43
O
CH3CH2CH2CCH3
63 D Option D — CH3CH2CH2CCH3 (a ketone) is reduced to pentan-2-ol (a secondary alcohol).

O OH
CH3CH2CH2CCH3 +
CH3CH2CH2CCH3
2 H 3O
O H
OH
1 LiAlH4 / ethoxyethane pentan-2-ol
CH3CH2CH2CCH3 CH3CH2CH2CCH3
64 A Option A — (CH3)2CHCOOH (a carboxylic
2 H3O+ acid) is reduced to methylpropan-1-ol (a primary alcohol).
H
(CH3)2CHCOOH (CH3)pentan-2-ol
2CHCH2OH
2 H3O+
methylpropan-1-ol
65 B Option A — Dehydration of propan-1-ol gives CH3CH=CH2 which is optically inactive.

H H H
H HH H HH H HH
dehydration
H C C C H dehydrationCH3CH
dehydration
dehydration CH2
H HH C CC C CC C CC H HH CHCH
CH
3CH3CH
3CH
CHCH
2CH
22
H H OH
H HH H HH OHOH
OH
remove
remove
remove
remove
Option B — Reduction of butanone gives CH3CH2CH(OH)CH3, which is optically active.
O OH
O OO OHOH
OH
reduction
CH3CH2CCH3 reduction CH3CH2CCH3
reduction
reduction
CHCH
CH
3CH3CH
CCH
32CH2CCH
2CCH
3 33 CHCH
CH
3CH CCH
32CH
3CH 2CCH
2CCH
3 33
H
H HH
chiral carbon
chiral carbon
chiral
chiral carbon
carbon
Option C — Addition of Br2 to 3-bromopropene gives CH2BrCHBrCH2Br, which is optically inactive.

B r2
CH2BrCH CH2 Br2BBrCH
2r2
2BrCHBrCH2Br
CHCH
2 BrCH
CH BrCH
BrCH
22
CH CH
CH
2 22
CHCHBrCHBrCH
2CH 2Br2Br
2BrCHBrCH
2BrCHBrCH 2Br
Option D — Addition of H2 to but-2-ene gives CH3CH2CH2CH3, which is optically inactive.

H2
CH3CH CHCH3 CH
H2 HH
22 3
CH2CH2CH3
CHCH
CH
3CHCHCH CHCH
CHCH
CHCH3 CH CH
3CH
CH CH
32CH
3CH
CH
22CH
2CH 23CH
2CH
3 3 3 3 33
66 A Option A — An ester is formed when a carboxylic acid reacts with an alcohol. The reaction is known as
esterification.
67 D Option D — The rate of esterification is slow. Hence concentrated sulphuric acid is used as a catalyst to
speed up the reaction.
44
O O
68 B Option B — CH3 C O H+H O CH3 CH3 C O CH3 + H2O

carboxylic acid + alcohol ester + water
69 D Option D — The flavours and fragrances of many fruits are due to a mixture of natural esters. Esters
are also used in artificial flavourings.
70 B Option A — Combustion of ethanol produces carbon dioxide.

Option C — Oxidation of ethanol produces ethanoic acid.
Option D — The reaction between ethanol and ethanoic acid (from oxidation of ethanol) produces ethyl
ethanoate.
71 C Option C — Hydrolysis of ester X produces ethanol and methylpropanoic acid.
O O
hydrolysis
(CH3)2CH C O CH2CH3 (CH3)2CH C OH + CH3CH2 OH
methylpropanoic acid ethanol
ester X
72 D Option D — Hydrolysis of the amide produces a carboxylic acid.
CH2CH2CONH2 CH2CH2COOH
+ H2O + HCl + NH4Cl

73 C Option C — H H H O H
H C C C O C C H
H H H H

propan-1-ol from ethanoic acid
74 A Option A — The rate of esterification is slow. Hence concentrated sulphuric acid is used as a catalyst to
speed up the reaction.
75 B Option B — The structure of ethyl benzoate is shown below:

O
C O CH2CH3
this part this part

comes from comes from
benzoic acid ethanol
45
76 C Option C — Propanamide is produced from propanoic acid by adding solid ammonium carbonate to an
excess of the acid.
O O O O
– +
2CH3CH COH + (NH4)2CO32CH CH CO
2CH
– CH+ CO NH + CO2 + H2O
2CH3CH
2COH + (NH
2 ) CO
4 2 3 3 2
NH
3
4
+2 CO + 4H O
2 2
When the reaction is complete, heat the mixture under reflux. The ammonium salt dehydrates
and produces propanamide.
O O O O
– +
CH3CH2COCH
–
NH
3
CH
4
+ CO NH
2
3 2
CH CH CNH2 + H2O
4 CH CH CNH 3+ H2 O
2 2
propanamide
propanamide
77 B Option B — Alkaline hydrolysis of ethyl propanoate produces sodium propanoate and ethanol. The products
are separated by fractional distillation.
O O
– +
CH3CH2 C O CH2CH3 + NaOH CH3CH2 C O Na + CH3CH2OH
ethyl propanoate sodium propanoate ethanol
78 A
79 A
80 C Option C — The silver nitrate solution is added to follow the rate of hydrolysis of the haloalkanes. Halide
ions produced from the hydrolysis will form a precipitate with the silver ions.
Ag+(aq) + X–(aq) AgX(s)
81 C (1) and (2)

5VCF9 5VCF: 5VCF;
DIMPSPCVUBOF CSPNPCVUBOF JPEPCVUBOF

FUIBOPMTJMWFS FUIBOPMTJMWFS FUIBOPMTJMWFS
OJUSBUFTPMVUJPO OJUSBUFTPMVUJPO OJUSBUFTPMVUJPO
XIJUFQSFDJQJUBUF DSFBNZQSFDJQJUBUF ZFMMPXQSFDJQJUBUF
The rate of hydrolysis of haloalkanes is related to how easily the C–X bond breaks. As the C–I
bond is weaker than the C–Br and C–Cl bonds, the C–I bond breaks most readily. Hence the rate
of hydrolysis of 1-iodobutane is the highest. A precipitate would first appear in tube Z.
As the C–Cl bond is the strongest, the bond is the most difficult to break. Hence the rate of
hydrolysis of 1-chlorobutane is the lowest.
46
(3) 1-halobutanes undergo hydrolysis to give butan-1-ol.
hydrolysis
CH3CH2CH2CH2X CH3CH2CH2CH2OH
1-halobutane butan-1-ol
82 B H H H H H H
Br2(aq)
C C H C C H + H C C H
H H
Br Br Br OH
(1) Both products are obtained via an addition reaction.

(2) Both products can be hydrolyzed to form the same diol.
H H
H C C H hydrolysis
H H
Br Br
H C C H
H H hydrolysis
OH OH
H C C H
Br OH
(3) CH2BrCH2OH can form hydrogen bonds with water while CH2BrCH2Br CANNOT.
83 B (1) CH3CH CH2=CH

CH32CH CH=2CH
does
2
NOT
H2 exhibit geometrical isomerism because it has two hydrogen atoms
attached to one carbon of the double bond.
H2 CH3CH2CH2CH3
(2) Both alkenes react with hydrogen to form butane.
CH3CH=CHCH3 butane
CH3CH2CH=CH2 H2
H2 CH3CH2CH2CH3
CH3CH=CHCH3 butane
(3) The two alkenes react with bromine to form different bromobutanes.
Br2
CH3CH2CH=CH2 CH3CH2CHBrCH2Br
1,2-dibromobutane
Br2
CH3CH=CHCH3 Br CH3CHBrCHBrCH3
CH3CH2CH=CH2 2
CH32,3-dibromobutane
CH2CHBrCH2Br
1,2-dibromobutane
Br2
CH3CH=CHCH3 CH3CHBrCHBrCH3
2,3-dibromobutane
47
84 D (2) In an elimination reaction, atoms or groups of atoms are removed from two adjacent atoms
(usually carbon atoms) of the reactant molecule.
In Step 2, HBr is removed from CH3CHBrCH2CH3.
(3) In Step 1, the Br group in CH3CHBrCH2CH3 is substituted by an –OH group.
85 B (1) and (3) Sulphur dichloride oxide reacts with butan-1-ol to produce 1-chlorobutane. Sulphur dioxide
and hydrogen chloride are given off.
reflux
CH3CH2CH2CH2OH + SOCl2 CH3CH2CH2CH2Cl + SO2 + HCl
86 A (1) Red phosphorus reacts with iodine to give phosphorus triiodide.

2P + 3I2 2PI3

2P + 3I2 2PI3 2P + 3I2 2PI3
(2) The organic product X obtained has NO carbon atom with four different groups attached to it.
Thus, it is optically inactive.
PI3
CH2OH CH2I
reflux
PI3 PI3
CH2OH CH2I CH2OH CH2I
reflux organic product X reflux
organic product X organic product X
CH2OH

CH2OH CH2OH
(3) Organic product X can also be obtained when reacts with hydrogen iodide.
However, when concentrated sulphuric acid reacts with sodium iodide, the acid oxidizes the iodide
ions to iodine and produces very little hydrogen iodide.
Thus, concentrated phosphoric acid should be used instead.
87 A (1) Alcohol X undergoes dehydration in the reaction.

H H H
dehydration
H C C C H CH3CH CH2
H H OH
remove
(2) Primary alcohols are the most difficult to dehydrate. Alcohol X is a primary alcohol. Thus, the
dehydration should be carried out by heating alcohol X with concentrated sulphuric acid.
(3) Alcohol X does NOT contain any carbon atom with four different groups attached to it. Thus, it has NO
chiral centre.
88 D (1) Ethanol undergoes oxidation.

(3) The purple permanganate ions change to colourless manganese(II) ions in the process. Thus, the
purple colour of the reaction mixture fades.
48
89 C (2) and (3) Compound X may be an alcohol that undergoes oxidation in the reaction. The reaction mixture
changes from orange to green as the dichromate ions are reduced to chromium(III) ions.
90 A (1) The two alcohols have the same carbon skeleton and functional group. They differ only in the
position of the functional group. Thus, they are position isomers.
(2) Both alcohols give propene when they undergo dehydration.
H H H
H C C C H dehydration
H H OH
CH3CH CH2
remove propene
dehydration
H H H
H C C C H
H OH H
remove
(3) Both alcohols undergo oxidation when warmed with acidified potassium dichromate solution.
Thus, they CANNOT be distinguished by warming with acidified potassium dichromate solution.
91 D (1) CH2=CHCH2OH decolorizes aqueous bromine while CH3CCH3 does NOT.

(2) CH2=CHCH2OH undergoes oxidation when warmed with acidified potassium dichromate solution
O
while CH3CCH3 does NOT.

(3) CH2=CHCH2OH gives hydrogen chloride fumes when mixed with phosphorus pentachloride while
O
CH3CCH3 does NOT.

92 A The compound is ethyl ethanoate, an ester.
(2) An ester CANNOT conduct electricity.
(3) The ester is produced from ethanol and ethanoic acid.
93 B
94 D (1) Esterification, a reversible reaction, occurs. Thus, the reaction CANNOT go to completion.
(2) The rate of esterification is slow. Hence concentrated sulphuric acid is used as a catalyst to speed
up the reaction.
49
(3) O CH3 O

CH3 C O H+H O C CH3 CH3 C O C(CH3)3 + H2O
CH3
95 A (1) Propan-1-ol undergoes oxidation with acidified potassium dichromate solution.

(2) Propan-1-ol undergoes esterification with ethanoic acid.
96 D (1) The ester comes from the reaction between ethanoic acid and an alcohol. Thus, the second word
of its IUPAC name is ethanoate.
CH3CH
COOCH 2CHCH
3COOCH 2CH23CH3
2CHCH
CH3CH3
this this
partpart
comes
comes
fromfrom
ethanoic acidacid
ethanoic
(2) This ester contains 1 chiral carbon atom.
chiralchiral
carbon
carbon
CH3CH
COOCH 2CHCH
3COOCH 2CH23CH3
2CHCH
CH3CH3
(3) This ester comes from the reaction between ethanoic acid and an alcohol. Thus, it produces
ethanoic acid on acid hydrolysis.
97 A (1) Alkaline hydrolysis of compound Q gives CH3OH and CH3CH2CH2COONa.

O O
CH3CH2CH2 C O CH3 + NaOH CH3CH2CH2 C O–Na+ + CH3OH
The products can be separated by fractional distillation. CH 3OH is obtained as distillate.

CH3CH2CH2COONa remains in the solution as it is less volatile.
98 B (2) Aspartame contains an amide functional group and an ester functional group. Hydrolysis of an
amide produces a carboxylic acid while hydrolysis of an ester produces a carboxylic acid and an
alcohol.
O COOCH3
H2N CH C NH CHCH2
CH2COOH
aspartame
O COOH
hydrolysis
H2N CH C OH + H2N CHCH2 + CH3OH
50 CH2COOH
99 D When propene reacts with HBr(g), an addition reaction occurs.
When a molecule HA adds to an asymmetric alkene, the major product is the one in which the hydrogen
atom attaches itself to the carbon atom already carrying the larger number of hydrogen atoms.
Thus, for the reaction between propene and HBr(g), 2-bromopropane is the major product.
CH3 H H H H H H H
HBr
C C H C C C H + H C C C H
H H
H Br H H H Br
2-bromopropane 1-bromopropane
this carbon atom carries (major product) (minor product)

more hydrogen atoms
100 A
101 B Propan-1-ol gives hydrogen chloride fumes when mixed with phosphorus pentachloride.
CH3CH2CH2OH + PCl5 CH3CH2CH2CI + POCl3 + HCl

propan-1-ol 1-chloropropane
102 C A tertiary alcohol has three alkyl groups attached to the carbon bearing the –OH group.
Hexan-3-ol is NOT a tertiary alcohol as there are only two alkyl groups attached to the carbon bearing
the –OH group.
H H H OH H H
H C C C C C C H
H H H H H H
103 B Butan-2-ol undergoes dehydration when heated with excess concentrated sulphuric acid. But-1-ene and
but-2-ene are formed.
H H H H
dehydration
H C C C C H CH2 CHCH2CH3
H OH H H but-1-ene
(minor product)
remove
H H H H
dehydration
H C C C C H CH3CH CHCH3
H OH H H but-2-ene
(major product)

remove
But-1-ene has only one alkyl group attached to the carbon atoms of the C=C bond while but-2-ene has
two. But-2-ene is the more substituted alkene and hence the major product of the reaction. 51
104 C When heated under reflux with acidified potassium dichromate solution, propan-1-ol is oxidized to
propanoic acid rather than to propanal.
105 C On reduction with LiAlH4, pentanoic acid is converted to pentan-1-ol.
106 C The reaction between ethanoic acid and ethanol is esterification.
107 D The rate of esterification is slow. A catalyst such as concentrated sulphuric acid is used to speed up the
reaction.
108 B But-2-en-1-ol can decolorize aqueous bromine because it contains a C=C bond.
109 A
110 D Both butan-1-ol and butanal undergo oxidation when warmed with acidified potassium dichromate
solution. Thus, they CANNOT be distinguished by warming with acidified potassium dichromate
solution.
Unit 32 Synthesis of carbon compounds
Fill in the blanks

1 a) i) Br2 (in organic solvent) (1)
ii) Br2 (aq) (1)
iii) H2 / Ni catalyst (1)
iv) HBr(g) (1)
– –
v) MnO4 / OH (1)
b) i) conc. H2SO4 or conc. H3PO4 or Al2O3, heat (1)
ii) reflux with conc. HCl, ZnCl2 catalyst; or mix with PCl5; or reflux with SOCl2 (1)
iii) reflux with NaBr + conc. H2SO4; or reflux with red P + Br2 (1)
iv) reflux with Nal + conc. H3PO4; or reflux with red P + I2 (1)
+
v) heat with K2Cr2O7 / H3O , distil off the product (1)
vi) CH3COOH, conc. H2SO4, heat (1)
+
c) i) reflux with K2Cr2O7 / H3O (1)
+
ii) 1 LiAlH4 / ethoxyethane; 2 H3O (1)
iii) concentrated H2SO4, heat (1)
iv) reflux with NaOH(aq) (1)
v) 1 NH3(aq); 2 heat (1)
vi) HCl(aq), heat (1)
vii) reflux with NaOH(aq) (1)
52
True or false
2 F Ethanol and water can be separated by fractional distillation.
3 T Ethoxyethane and water are immiscible.
4 T Concentrated sulphuric acid reacts with sodium bromide to give hydrogen bromide.
Butan-1-ol reacts with hydrogen bromide to give 1-bromobutane.
5 F Concentrated hydrochloric acid is NOT a drying agent.
6 F During re-crystallization, the minimum amount of hot solvent should be used to dissolve the crude solid
product.
7 A
8 A Option A — Trichloroethene reacts with Br2(g) to give CBrCl2CHBrCl, a chiral product.
Cl Cl
Cl Cl
C C + Br2 Cl C C H
Cl H
Br Br

chiral carbon
9 D Option A — CH
CH22 CH22 ++ HCl
CH HCl CH33CH
CH CH22Cl
Cl
CH22
Option B — CH CHCl ++ HH22
CHCl CH33CH
CH CH22Cl
Cl
CH33CH
Option C — CH CH22OH
OH ++ PCl
PCl55 CH33CH
CH CH22Cl
Cl ++ POCl
POCl33 ++ HCl
HCl
10 A Option A — When a molecule HA adds to an asymmetric alkene, the major product is the one in which
of hydrogen atoms.
H H H H
H H HBr
C C H C C CH2OH + H C C CH2OH
H CH2OH
H Br Br H
carries more
hydrogen atoms
HBr
H H
H C C CH2Br
H Br 53
(( ))
O
O C
CH3
C
CH3
11 C Option C — Compound Y is a ketone. It is obtained via the oxidation of a
(( ))
OH
OH CH
CH3
secondary alcohol CH .
CH3
12 D Option D — [O]
C2H5OH CH3CHO
molar mass 46.0 g mol
–1
44.0 g mol
–1
1 mole (44.0 g) of ethanal can be obtained from 1 mole (46.0 g) of ethanol. Thus, the
maximum mass of ethanal that can be obtained from 2.3 g of ethanol is 2.2 g.
13 C Option C — 3,3-dimethylbutan-2-ol is a secondary alcohol. It is obtained via the reduction of a ketone.
CH3 O CH3 H
reduction
CH3 C C CH3 CH3 C C CH3
CH3 CH3 OH
ketone 3,3-dimethylbutan-2-ol
14 D Option D — From the given example, the reaction involves bonding one O to one carbon of the C=C
bond, and shifting one H to the adjacent carbon.
Thus, the catalytic oxidation of but-2-ene probably takes place as shown below:
O
1
CH3CH=CHCH 3 + O2 CH3CH2CCH3
2
15 C Option C — O

C O CH2CH2CH3
this part this part comes from

comes from CH3CH2CH2OH
COOH
54
16 D Option D — OH O CH3
Br C C O CH
CH3
this part
comes from
Br propan-2-ol
17 C Both alcohol and carboxylic acid react with SOCl2 to form an alkyl chloride and an acid chloride.
The acid chloride reacts with CH3OH to form an ester.
O O O
SOCl2 CH3OH
HO CH2 C OH Cl CH2 C Cl Cl CH2 C O CH3
18 C
19 C Option C — Step 1 involves the hydrolysis of CH3CH2CH2Br to form CH3CH2CH2OH.

Step 2 involves the oxidation of CH3CH2CH2OH to form CH3CH2COOH.
20 C Option C — CH3COCH3 is reduced to CH3CH(OH)CH3 in Step 1.
21 D Option D — CH3CH(OH)CH3 undergoes dehydration when heated with Al2O3.
H H H
dehydration
H C C C H CH3CH CH2
H OH H propene
remove
22 B Options A, C and D — dehydration oxidation

CH3CH=CH2 CH3CH2CH2OH CH3CH2COOH
esterification
CH3COOCH2CH2CH3
23 D Option D — O O
Step 1
C C
CH3 dehydration
CH3
OH
hydrogenation Step 2
C
CH3
55
24 B Option B — Compound Z (C4H8O2) is an ester formed from methanol and a carboxylic acid. Thus,
compound Y is probably propanoic acid.
Compound Y is obtained via the oxidation of compound X. Thus, compound X may be
propanal.
25 B Option A — Oxidation and esterification are included in the flow diagram.
PYJEBUJPO
QSPQBOBM QSPQBOPJDBDJE
FTUFSJGJDBUJPO
;
NFUIBOPM
Option B — The orange dichromate ions change to green chromium(III) ions in the reaction with compound
X.
Option C — In the esterification between methanol and Y, concentrated sulphuric acid acts as a
catalyst.
Option D — The systematic name of Z is methyl propanoate.
26 D Option D — Compound X could be propanoic acid.
K2Cr2O7 / H3O+ NH3

CH3CH2CHO CH3CH2COOH CH3CH2COO–NH4+
heat
CH3CH2CONH2
27 D Option D — Compound X could be 3-phenylpropanoic acid.
CH CHCOOH CH2CH2COOH CH2CH2COCl

H2 / Pt catalyst PCl5
28 B Option B — Fractionating column is required in fractional distillation, NOT in simple distillation.
29 A Option A — C6H5COCl + C6H5OH C6H5COOC6H5 + HCl

1.80 g 1.30 g
1 mole (140.5 g) of C6H5COCl produces 1 mole (198.0 g) of C6H5COOC6H5.

198.0 g
Theoretical yield of ester = 1.80 g x
140.5 g
= 2.54 g

1.30 g
Percentage yield of ester = x 100%
2.54 g

= 51.2%
56
30 D Option D — C6H6 + Br2 C6H5Br + HBr
20.0 g 0.310 mol 26.0 g
20.0 g
Number of moles of C6H6 used = –1
78.0 g mol
= 0.256 mol
0.256 mole of C6H6 reacted with 0.256 mole of Br2. Thus, Br2 was in excess.
Theoretical yield of C6H5Br = 0.256 mol x 156.9 g mol–1
= 40.2 g

26.0 g
Percentage yield of C6H5Br = x 100%
40.2 g

= 64.7%
31 C (1) and (3) — Mineral acids are used to obtain benzoic acid from its sodium salt.
C6H5COO– + H+ C6H5COOH
32 D Option B and C — Distillation and fractional distillation are common separation and purification methods
for liquid products.
Option D — Re-crystallization is a common separation and purification methods for solid products (e.g.
benzoic acid).
33 C Option C — C6H5CONH2 C6H5COOH

7.60 g 4.94 g
1 mole (122.0 g) of C6H5COOH can be obtained from 1 mole (121.0 g) of C6H5CONH2.

122.0 g
Theoretical yield of C6H5COOH = 7.60 g x
121.0 g
= 7.66 g

4.94 g
Percentage yield of C6H5COOH = x 100%
7.66 g
= 64.5%
34 C
35 A Option A — Anhydrous calcium chloride is a common drying agent.
36 A (3) There is NO reaction between cyclohexene and anhydrous calcium chloride.
57
37 C Option C — Y is chiral. It has enantiomers.
OH
CH3CH2 CH
chiral carbon
Z has two different atoms or groups attached to each carbon of the double bond. Thus, it
has geometrical isomers.
38 C (1) and (3) O OH

reduction
CH3CH2 C CH3CH2 CH
X Y
dehydration
CH3CH CH
39 B Option B — " $)0
4UFQ /B0) BR
SFGMVY

TPMVUJPO
4UFQ EJTUJM
EJTUJMMBUF# SFTJEVF$
,#S DPOD)40 BDJEJGZ
$)#S TPMJE%
Compound A is an ester. It undergoes alkaline hydrolysis in Step 1 to give an alcohol and

the sodium salt of a carboxylic acid.
Distillate B undergoes substitution to give C2H5Br. Thus, it is probably CH3CH2OH.
Residue C should be C6H5COO–Na+.
Solid D is C6H5COOH.
40 B (2) Ester A is formed from the reaction between ethanol and benzoic acid. Its systematic name is ethyl
benzoate.
41 A (3) The reagent and condition used in Step 2 may be

• reflux with conc. HCl + ZnCl2 catalyst; or
• mix with PCl5; or
• reflux with SOCl2.
58
42 D (2) and (3) $)$)$)
GSFFSBEJDBMTVCTUJUVUJPO $M H
TVOMJHIU
NPOPDIMPSJOBUFE NPOPDIMPSJOBUFE
DPNQPVOE" DPNQPVOE#
/B0) BR
/B0) BR

IZESPMZTJT IZESPMZTJT
SFGMVY SFGMVY
BMDPIPM$ BMDPIPM%
,$S0)0 ,$S0)0
PYJEBUJPO PYJEBUJPO
SFGMVY SFGMVY
DBSCPYZMJD LFUPOF'
BDJE&
43 C (1) and (3) Alcohol D gives ketone F upon oxidation. Thus, it is probably a secondary alcohol.
Compound B undergoes substitution to give secondary alcohol D. Thus, it is probably
2-chloropropane.
Cl OH O
hydrolysis oxidation
CH3CHCH3 CH3CHCH3 CH3CCH3
2-chloropropane alcohol D ketone F
(2) Alcohol C gives carboxylic acid E upon oxidation. Thus, it is probably a primary alcohol, propan-1-ol.
44 A (1) and (2) COOH

CHO
Step 1
oxidation
reduction CH2OH CH2OCOCH3
Step 3
Step 2
esterification
45 A (1) and (2) Step 1

BrCH2CH CHCH2Br HOCH2CH CHCH2OH
hydrolysis
compound A
addition Step 2
Step 3
CH2 CClCH CH2 HOCH2CHCICH2CH2OH
dehydration
polymerization
CH2CCI CHCH2 n
neoprene
46 D
47 B (2) Heating the reaction mixture under reflux prevents any loss of the reaction mixture and favours the
oxidation of propan-1-ol to propanoic acid rather than to propanal.
59
48 B (2) Ethoxyethane and water are immiscible. They can be separated by using a separating funnel.
49 A (3) Without releasing the pressure, the liquid in the separating funnel will NOT drain out of the funnel.
50 B Fractional distillation can be used to separate a mixture of miscible liquids with different boiling points.
51 C Heating ethanol and methanoic acid in the presence of concentrated sulphuric acid produces ethyl
methanoate.
52 A
53 C Propanoic acid produces propan-1-ol upon reduction with LiAlH4.
54 C Alkaline hydrolysis of ethyl benzoate produces ethanol and sodium benzoate.

O O
C O CH3CH3 + NaOH C O–Na+ + CH3CH2OH
ethyl benzoate sodium benzoate ethanol
Unit 33 Important organic substances
Fill in the blanks

1 fats; oils; saponification
2 calcium; magnesium
3 scum
4 non-biodegradable
5 hydrogen
6 condensation
7 monosaccharides
8 glucose; fructose
9 triglyceride
10 amino acid
60
True or false
11 T
12 F
13 F Most soapless detergents nowadays are biodegradable.
14 F When soaps are added to hard water, scum forms.
15 T Synthetic detergents often contain phosphate salts as ‘builders’. When the phosphates go into rivers and
seas, they become the nutrients of algae. As a result, algae growth will increase rapidly.
16 T Nylon is produced via condensation polymerization.
17 F Permanent dipole-permanent dipole attractions, NOT hydrogen bonds, exist between the polymer chains
of poly(ethylene terephthalate).
0δ– 0δ– 0δ– 0δ–
$δ+ $δ+ 0 $) $) 0 $δ+ $δ+ 0 $) $) 0
0δ– 0δ– 0δ– 0δ–
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LFZ
QFSNBOFOUEJQPMFQFSNBOFOUEJQPMFBUUSBDUJPO
18 T Polysaccharides such as starch yield a large number of monosaccharide molecules upon hydrolysis.
H3O+
Starch many glucose molecules
19 T Alkaline hydrolysis of a triglyceride produces glycerol and a mixture of salts of long-chain carboxylic
acids.
H O H O
H C O C R1 H C O H R1 C O– Na+
O O
NaOH(aq)
H C O C R2 H C O H + R2 C O– Na+
O O
H C O C R3 H C O H R3 C O– Na+
H H
triglyceride glycerol sodium carboxylates

(soap)
61
20 F Commercial hydrogenation of a vegetable oil is partial in order to obtain a fat that is solid at room
temperature but melts readily upon baking or consumption.
21 B Option B — Mineral acids (e.g. HCl(aq)) are used to obtain salicylic acid from its sodium salt.
OH OH
COO– + H+ COOH
salicylic acid
22 C Option C — O
O C CH3 OH
COOH COOH
13.5 g 7.60 g
1 mole (180.0 g) of aspirin produces 1 mole (138.0 g) of salicylic acid.

180.0 g
Mass of aspirin converted to salicylic acid = 7.60 g x
138.0 g
= 9.91 g
9.91 g
Percentage of aspirin converted to salicylic acid = x 100%
13.5 g
= 73.4%
23 D Option D — The hydrocarbon ‘tail’ is soluble in grease and oil, i.e. hydrophobic. The anionic ‘head’ is
soluble in water, i.e. hydrophilic.
24 C Option C — When fats or oils are heated with an alkali, they are hydrolyzed first to form glycerol
and carboxylic acids. The acids then react with the alkali (sodium hydroxide or potassium
hydroxide) to form sodium or potassium salts which are soaps. Such reactions are called
saponification.
25 A Option A — Concentrated sodium chloride solution lowers the solubility of soap in water. The soap
separates from the solution and floats on the surface.
26 D
62
27 B Option B — The chemical equation for the reaction between animal fat X and sodium hydroxide solution
is shown below.
O H
H
R C O C H
O H C OH
R C O C H + 3NaOH H C OH + 3RCOO– Na+

O
H C OH
R C O C H
H
H
animal fat X glycerol
28 A Option A — Detergents I and IV are soaps. They would form scum with hard water.
29 C Option C — Detergent III is non-biodegradable.
30 B Option B — Detergents II and III are soapless detergents. They are made using hydrocarbons obtained
from petroleum.
31 B Option A — A soap can decrease the surface tension of water.

Option C — A soap forms scum in hard water. It does NOT work well in hard water.
Option D — A typical soap particle contains a hydrophobic hydrocarbon ‘tail’ and a hydrophilic anionic
‘head’.
H H H H H H H H H H H H H H H H H O
H C C C C C C C C C C C C C C C C C C O – K+
H H H H H H H H H H H H H H H H H
hydrophobic hydrocarbon ‘tail’ hydrophilic

anionic ‘head’
The emulsifying action of a soap is due to its hydrocarbon ‘tail’ and anionic ‘head’.
32 C The detergent shown is a soapless detergent.

Option A — This detergent is biodegradable.
Option B — Sea water contains a relatively high concentration of magnesium salts.
A soapless detergent forms soluble substances with magnesium ions. Thus, it does NOT form
scum in sea water.
O

O S O–

Option D — The hydrophilic part responsible for the cleaning action is O .
63
O
33 D Option D — The ionic ‘head’ of a soap particle is usually a C O– group.
34 A Option A — Sea water contains a lot of metal ions, such as magnesium ion.
A soap solution forms scum in sea water. A proper lather cannot form until the soap has
reacted with all the magnesium ions in the sea water.
Option B — The tap water in Hong Kong is soft water.
35 A Option A — Sodium carbonate reacts with calcium ions and magnesium ions in hard water to form
insoluble carbonates, thus reducing the hardness of water.
Ca2+(aq) + CO32–(aq) CaCO3(s)
2+ 2–
Mg (aq) + CO3 (aq) MgCO3(s)
36 D Option D — The calcium carbonate deposit can be removed by an acid. Vinegar contains ethanoic
acid.
CaCO3(s) + 2H+(aq) Ca2+(aq) + CO2(g) + H2O(l)
37 B Option B — Electric plugs are made of plastics that can withstand very high temperatures.
38 D Option A — Hydrogen bonds exist between nylon polymer chains.

) 0 ) 0
/ $)
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$ / $)
/ $
) 0 )
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/ $ $)
$ / $)
/ $
LFZ
) 0 ) IZESPHFOCPOE
Option D — Nylon is a polyamide.
H O
N (CH2)6 N C (CH2)4 C
H O
64
39 B Option A — Compound X contains carboxyl groups, NOT carbonyl groups.
Option C — Polyester A is a condensation polymer.
H2O H2O H2O
O O O
...... O H + HO C C OH + H O CH2 CH2 O H + HO C ......
O O
repeated condensation
C C O CH2 CH2 O
H2O released n

Option D — Permanent dipole-permanent dipole attractions exist between the polymer chains of A.
0δ– 0δ– 0δ– 0δ–
$δ+ $δ+ 0 $) $) 0 $δ+ $δ+ 0 $) $) 0
0δ– 0δ– 0δ– 0δ–
$δ+ $δ+ 0 $) $) 0 $δ+ $δ+ 0 $) $) 0
LFZ
40 D Option D — 1,2-dichloroethane undergoes hydrolysis to give compound Y.
NaOH(aq)
Cl CH2 CH2 Cl HO CH2 CH2 OH
1,2-dichloroethane compound Y
41 B Option B — Open-chain glucose contains 4 chiral carbons (marked with *).
H O
C
H C* OH
HO C* H
H C* OH
H C* OH
CH2OH
65
42 A Option A — Simple sugars, such as glucose, contain –OH group which is responsible for their high water
solubility.
Different forms of glucose:
H O
1
C 6 6
CH2OH CH2OH
2
H C OH 5 5
C O C O
3
H H H OH
HO C H
H H
4
4
C C1 4
C C1
H C OH OH H OH H
5
HO OH HO H
H C OH 3 C C2 3 C C2
6
CH2OH H OH H OH
open-chain glucose one of the cyclic forms one of the cyclic forms
— α-glucose — β-glucose
43 A Option A — Fructose is a monosaccharide. It cannot be cleaved into smaller, simpler carbohydrates by

hydrolysis.
44 A Option A — Vegetable oils contain triglycerides formed from a high proportion of unsaturated carboxylic
acids. When hydrogen is passed through a vegetable oil in the presence of a catalyst, hydrogen
adds to the C=C bonds and turns the oil into a solid fat. An addition reaction occurs.
45 D Option D — Serine contains a basic group (–NH2) and an acidic group (–COOH). In dry solid state, it
exists as a dipolar ion. In a strongly acidic solution, it is present mainly as a cation.
+ +
NH3 NH3
+
–
H
HOCH2CHCOO HOCH2CHCOOH
dipolar ion
46 A Option A — Two molecules of amino acid X undergo condensation to form the given dipeptide as shown
below:
H O H O
H N C C OH + H N C C OH
H CH3 H CH3
amino acid X amino acid X
H O H O
H N C C N C C OH + H2O
H CH3 H CH3
a dipeptide
66
47 D Option D — The amide / peptide link of the given compound can be hydrolyzed as shown below:
C N + H2O
C OH + H N
48 D
49 B (2) Soaps are prepared by boiling fats or oils with a strong alkali, usually sodium hydroxide solution.
50 A (3) Detergent CANNOT soften hard water.
51 B (1) Hard water contains a great amount of dissolved calcium salt and magnesium salt.
(2) Sea water contains a relative high concentration of magnesium salts. Thus, sea water is hard
water. O
(3) The tap water in Hong Kong is soft water.
group S O–
O
O
52 D (1) The ionic ‘head’ of a soapless detergent particle is usually a sulphonate group
group S O– or
O
O
or sulphate group O S O . –
O
O
(3) Soapless detergents form soluble substances with calcium ions or magnesium ions. Thus, they
or sulphate do not O
group S
form scum in hard water and can clean effectively in hard water.
O
53 B The detergent shown is a soap.
(1) The detergent is biodegradable.
(3) Soap is UNSUITABLE for treating oil spillage on sea water.
Sea water contains a relatively high concentration of magnesium salts. A soap forms scum in sea
water.
54 A (2) Soap forms scum in hard water while soapless detergent does NOT.
(3) Most soapless detergents nowadays are biodegradable.
67
55 A (1) When the phosphates go into rivers and seas, they become the nutrients of the algae. As a result,
algae will grow suddenly. Sometimes algae may grow so that they form a thick layer on the water
surface. Light cannot enter the deeper level of the water. As a result, the plants underneath cannot
carry out photosynthesis and they die.
56 B (2) Compound X is more viscous than compound Y.

The viscosity of a liquid depends on
• the strength of attractive forces between molecules; and
• the tendency of molecules to become entangled with each other.
Compared with compound Y, compound X has a greater number of electrons in each molecule.
Thus, the van der Waals’ forces between its molecules are stronger. Furthermore, because of the
shape, molecules of compound X tend to become entangled with each other.
(3) Alcohol Z is glycerol.
C17H33C O CH2 H O CH2

O O
NaOH(aq)
C17H33C O CH + 3CH3OH 3C17H33C O CH3 + H O CH
O
compound Y
C17H33C O CH2 H O CH2
compound X alcohol Z
( )
F F
C C
57 A (3) Polytetrafluoroethene F F n is used for surfacing non-stick frying pans.
58 C (2) Nylon is a condensation polymer.
H2O H2O H2O

H O H
...... OH + H N (CH2)6 N H + HO C (CH2)4 C OH + H N ......
H O
H O
N (CH2)6 N C (CH2)4 C
H2O released H O n
68
59 B (1) Polymer X is formed from two different monomers.
O O
HO C C OH HO CH2 CH2 OH

(2) Permanent dipole-permanent dipole attractions exist between the chain of polymer X.
0δ– 0δ– 0δ– 0δ–
$δ+ $δ+ 0 $) $) 0 $δ+ $δ+ 0 $) $) 0
0δ– 0δ– 0δ– 0δ–
$δ+ $δ+ 0 $) $) 0 $δ+ $δ+ 0 $) $) 0
LFZ
(3) Polymer X can be broken down by hydrolysis of the ester linkage.
O O
C C O CH2 CH2 O
60 B (1) Poly(ethylene terephthalate) is a common polyester. It is formed by condensation polymerization.
H2O H2O H2O

O O O
...... O H + HO C C OH + H O CH2 CH2 O H + HO C ......
O O
C C O CH2 CH2 O
H2O released n

(2) Poly(ethylene terephthalate) is a thermoplastic. There is NO covalent bond between the polymer
chains.
69
61 D (1) The two given molecules can undergo addition polymerization to form an addition polymer.
H H H3C H
...... + C C + C C + ......
H H H H
H H H3C H
C C C C
H H H H
(2) The amine and acid functional groups at both ends of the given molecules react to form amide
linkages, releasing water molecules.
H2O H2O H2O

H O H
H O
H O
N (CH2)6 N C (CH2)4 C
H2O released H O n

(3) The two amino acid molecules can undergo a condensation reaction to form a dipeptide. A water
molecule is eliminated.
H O CH3 O
H H H H
amino acid 1 amino acid 2
H O CH3 O
H H H H
a dipeptide
A polypeptide can be obtained by adding amino acid molecules to the dipeptide.
70
4 3 2 1
2CH
62 D (1) HOCH 2CH
2COOH
This monomer contains two functional groups (–OH group and –COOH group).
The –COOH group is the principal functional group, i.e. butanoic acid.
The –OH group attached to the fourth carbon atom takes the prefix hydroxy, i.e. 4-hydroxybutanoic
acid.
(2) and (3) PHB is formed by condensation polymerization. The acid and alcohol functional groups at
the ends of the molecules react to form ester linkages, releasing water molecules.
H2O H2O
HOCH2CH2CH2COOCH2CH2CH2COOH + HOCH2CH2CH2COOCH2CH2CH2COOH + HOCH2CH2CH2COOCH2CH2CH2COOH
repeated reaction
CH2CH2CH2 COO
n
63 A (1) and (3) PBT is formed by condensation polymerization. The acid and alcohol functional groups at both
ends of the monomer molecules react to form ester linkages, releasing water molecules.
H2 O H2O H 2O
O O O
...... O H + HO C C OH + H O CH2 CH2 CH2 CH2 O H + HO C ......
O O
C C O (CH2)4 O
H2O released n

(2) PBT is a polyester. Permanent dipole-permanent dipole attractions exist between its polymer chains.
64 C (2) and (3) Hydrolysis of triglycerides produces glycerol and a mixture of long-chain carboxylic acids.
H O H O
H C O C R1 H C O H R1 C OH
O O
hydrolysis
H C O C R2 H C O H + R2 C OH
O O
H C O C R3 H C O H R3 C OH
H H long-chain
carboxylic acids
triglyceride glycerol
71
HO NH2
HO NH2
65 B (1) and (3) Paracetamol undergoes hydrolysis to give CH3COOH and .
O H O H
hydrolysis
CH3 C N OH CH3 C OH + H
O H
N OH
hydrolysis
CH3 C N OH
66 D (2) and (3) Pethidine contains amine functional group and ester functional group.
CH3
N amine functional group

CH2 CH2
CH2 CH2
C
COOCH2CH3
ester functional group
pethidine
67 B (1) and (3) CH3 CH3
N N
CH2 CH2 CH2 CH2
+ NaOH + CH3CH2OH
CH2 CH2 CH2 CH2
C C
COOCH2CH3 COO–Na+
68 B The correct explanation is that soap acts as an emulsifying agent.
69 D The hydrocarbon tail of soaps is hydrophobic. Soaps are made from natural fats and oils.
70 C Bacteria use up oxygen in the water during the decomposition of detergents. This makes the water of
some streams, rivers and seas smells badly due to oxygen depletion.
71 D Detergents with branched-chain hydrocarbons are non-biodegradable. They cause more harm to the
environment when compared to detergents with straight-chain hydrocarbons.
72 A
73 B Soapless detergents do not form scum with either soft water or hard water.
72
74 D When a mixture of fat and concentrated sodium hydroxide solution is heated for some time, salts of
carboxylic acids are formed. These salts of carboxylic acids are soaps. This reaction is saponification.
H O H O
– +
H C O C R1 H C O H R1 C O Na
O O
NaOH(aq)
H C O C R2 H C O H + R2 C O–Na+
O O
H C O C R3 H C O H R3 C O–Na+
H H
triglyceride in fat glycerol salts of carboxylic acids

(soaps)

75 C Nylon is a thermoplastic. It softens upon heating.
76 D Cellulose is a natural polymer, NOT a disaccharide.
77 C Two amino acid molecules can undergo a condensation reaction to form a dipeptide. A water molecule
is eliminated between the –NH2 group of one amino acid molecule and the –COOH group of the other.
The amino acid units are linked by an amide functional group.
R O R1 O
H H H H
amino acid 1 amino acid 2
R O R1 O
H H H H
a dipeptide
73
Part B Topic-based exercise
1 C Option C — H H
4,5
C2H5
1 2 3
H C C C H
H CH3 H
The parent chain contains 5 carbon atoms, i.e. pentane.

A methyl group is attached to the second carbon atom, i.e. 2-methylpentane.
2 D Option D — H H
1
C
2 3 4 5 6
CH3 CH2 C CH2 CH2 CH2 CH3
The parent chain contains 6 carbon atoms, with the double bond between the first and
second carbon atoms, i.e. hex-1-ene.
An ethyl group is attached to the second carbon atom, i.e. 2-ethylhex-1-ene.
3 C Option C — 1
CHO
4 2
5
3
The parent chain of this aldehyde contains 5 carbon atoms, i.e. pentanal.
A methyl group is attached to the second carbon atom, i.e. 2-methylpentanal.
4 B Option B — O
3 2 1
Cl CH2 CH2 C
OH
The parent chain of this carboxylic acid contains 3 carbon atoms, i.e. propanoic acid.
A chloro group is attached to the third carbon atom, i.e. 3-chloropropanoic acid.
5 A Option A — O
2
3 1
OH
A methyl group is attached to the third carbon atom of the benzoic acid, i.e.
3-methylbenzoic acid.
74
6 C Option C — O
CH3CH2CH C O CH2CH3
CH3
this part this part
comes from comes from
2-methylbutanoic acid ethanol
OH O
Thus, the IUPAC name of this ester is ethyl 2-methylbutanoate.
5 4 3 2 1
CH3CH2 CH C CH3
7 A Option A — OH OHO O
5
CH3CH
45 4 3 3 2 2 1 1 O
CH23CH2CH CHC CCH3 CH3
This compound contains two functional groups, –OH group and C group. OH O
O O 5 4 3 2
CH3CH2 CH C
The C C group is the principal functional group. Thus, the compound is regarded as
O
a ketone. This ketone contains 5 carbon atoms. The second carbon atom bears the C
group, i.e. pentan-2-one.
The – OH group attached to the third carbon atom takes the prefix hydroxy, i.e.
3-hydroxypentan-2-one.
8 A Option A — O

NH2 CH2 CH2 C O CH3
this part comes from this part

propanoic acid, comes from
with an amino group methanol
attached to the
third carbon atom
Thus, IUPAC name of this ester is methyl 3-aminopropanoate.
9 A The first fraction collected contains the smallest alkane molecules. The molar mass and boiling point of
alkanes increase in the order X < Y < Z.
Option A — Volatility decreases in the order X > Y > Z, i.e. Y is more volatile than Z.
Option B — Z has a greater molar mass than Y.
Option C — Intermolecular forces in Y are stronger than those in X.
Option D — The boiling point of a compound depends on the strength of its intermolecular attractions,
NOT the strength of covalent bonds in molecules.
75
10 A Option A — The boiling point of a compound depends on the strength of its intermolecular attractions.
Compared with the other amines, molecules of CH3CH2CH2CH2NH2 are the longest and
somewhat spread-out.
This allows the greatest surface contact between the molecules.
Van der Waals’ forces in CH3CH2CH2CH2NH2 are thus the strongest. Hence it has the highest
boiling point.
11 B Option B — Both ethanol and pentan-1-ol can form hydrogen bonds with water. Thus, they are soluble
in water.
The following diagram shows the hydrogen bonding between ethanol molecules and water
molecules:
)
0
)
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)
0
)
0 LFZ
$)$) ) IZESPHFOCPOE
Alcohols with a long carbon chain in their molecules are much less soluble in water. This is
because these alcohols resemble alkanes more. Thus, the water solubility of pentan-1-ol is
lower than that of ethanol.
Pentane is insoluble in water.
Thus, the order of water solubility of the compounds is pentane < pentan-1-ol < ethanol.
12 A Option A — The volatility of amines decreases with an increase in chain length.

Molecules of primary amines can form hydrogen bonds with water molecules. As a result,
they are soluble in water.
The following diagram shows the hydrogen bonding between an ethanamine molecule and
water molecules.
)

)

0
/
)
)
$
)
)
$
) LFZ

0
IZESPHFOCPOE
)

Amines with a long carbon chain in their molecules are much less soluble in water. This is
because these amines resemble alkanes more. Thus, the water solubility of amines decreases
with an increase in chain length.
76
( ) ( ) ( )
O O O O
13 B Compound P H3C – O – C – CH2CH3 is anCH CH
Hester
33C –O –C
CH 2–
2while –O
CCH – 3 Q CH3CH2CH2 – C – O – H is a carboxylic
–compound
2CHH
acid.
Option A — Q can turn0 moist blue litmus paper red
0 while P cannot.
) )
Option B — Permanent) dipole-permanent dipole attractions
)
exist between molecules of P while hydrogen
bonds exists between molecules of Q.
Permanent dipole-permanent
0 dipole attractions
0 are less strong than hydrogen bonds. Thus,
P is more volatile than Q.
( ) ( )
$) O $ $) $O
Option C — Both P and Q can form hydrogen bonding with water. Q is miscible with water in all
3C – O – C – CH
Hproportions 02CH3) it can
because CHform
03CH2CH 2–C– – H)
0Ohydrogen
extensive bonds
0 with water.
) )
)
)
) )
0
0
0
)
)
)
) LFZ LFZ
IZESPHFOCPOE IZESPHFOCPOE
0
$) $
0 ) 0
)
)
)
0
LFZ
IZESPHFOCPOE
14 D Option D — There are 5 possible structural isomers for C6H14.
H H H H H H H H CH3 H H
H C C C C C C H H C C C C C H
H H H H H H H H H H H
H H H CH3 H H H CH3 H
H C C C C C H H C C C C H
H H H H H H H CH3 H
H CH3 CH3 H
H C C C C H
H H H H
77
H3CHH3C
3C
H3C Br BrBr Br H3CHH3C 3C
H3C Cl Cl
Cl Cl
H3C C C CC BrC C H C C C C CClC C
H3C H3HC3C C Br C BrBr H3C H3H 3
C3C C Cl C ClCl
HHC
H3CC
15 D Option A — 3C
3C CCC C CCl Cl
HC3C Cl and
Cl H3CC HHC3C
3C CCC C CBr are
HC3C Br Br
Br identical molecules.
H3C Cl H3C Br
H3C H3HC3C Cl ClCl H3C H3H C3C Br BrBr

H HHHH HH H H HH H H HH H
H H H H
H HHH H H H HH H HH
H HHCH CCCC CCOH OHH
C OH OHHHCH CCOC OOCO CCHC HH H
H C C OH H C O C H
H HCH CCC COH C OH OH
H HCH COC OCO CHC H H
Option B — H HHHH HH H andH HH H H HH H are functional group isomers.
H H H H
H HHH H H H H H H H H
CH3CHCH3CH
3 3
CH3
CH3 CH CH CH3CH
3 3
H3CHH3C3C
H3C CH3CH 3 3
H3C CH3
H3C H3HC3C CH3 CHCH 3 3
Option C — and are structural isomers.

H3CHH3C 3CH3C F FF F H3CHH3C3CH3C CH3CHCH3CH
3 3
HC F HC CCH
H3C3 H3HC3CC CCCFC CCF CF H3C3 H3HC3CC CCCCH C3CCH
3C
CH3 3
FCCFFCCFCC C CCH3CH CH3CH
3 3 FCCFFCCFCC C CF FF F
F trans CH
isomer
trans isomer F F
cisisomer
isomer
cis
F F transF transisomerCH
isomer 3
3 CHCH
3 3 F F Fcis isomer
cis F isomer
F F
Option D — trans
trans trans
isomer isomer
isomer and cis isomer
ciscis isomer
isomer
They are a pair of geometrical isomers.
16 C Option C — Six isomers are possible for C4H8.
H3C CH3 H3C H H3C H

C C C C C C
H H H CH3 H3C H
geometrical isomers
CH3CH2 H H2C CH2 CH2

C C
H H H2C CH2 H2C C CH3
( )
H Br
C C
17 A Option A — C2HBr3 Br Br does NOT have isomeric structures.
18 B Option B — There are 4 esters with the molecular formula C4H8O2.
O O
CH3CH2 C O CH3 CH3 C O CH2CH3
O O
H C O CH2CH2CH3 H C O CHCH3
CH3
78
19 B Option B — The melting point of a substance depends on intermolecular attractions as well as molecular
symmetry.
Among the four compounds, 2,2,3,3-tetramethylbutane has the most regular and symmetrical
structure. Its molecules can pack most compactly in the solid. The greatest amount of heat
is required to overcome the intermolecular forces between its molecules. Hence it has the
highest melting point.
20 C Option C — In a molecule of this compound, four different groups are attached to the second carbon
atom. The molecule is chiral and optically active.
H H H
H C C C H
F Cl H
chiral carbon
21 C Option C — This molecule contains 3 chiral carbons (marked with *).
CH3
*
* *
OH
CH
H3C CH3
22 B Option B — This molecules has a plane of symmetry. It does NOT exhibit enantiomerism.
Br Br
plane of symmetry
23 C Option C — An alkene undergoes an addition at the double bond with Br2. Thus, two Br atoms are
added to the adjacent carbon atoms of the double bond.
H H H Br H
Br2
H C C C H H C C C H
H H H H
H C H H C H
Br
79
24 B Option A — MHA contains a double bond. Its systematic name should include the suffix form -en.
Option B — CH3CH2CH2 H CH3CH2CH2 COOH
C C C C
CH3 COOH CH3 H
Thus, MHA exhibits geometrical isomerism.
of hydrogen atoms.
CH3 CH3
C2H5 CH3
C C2H5 C Br C2H5 C D
DBr +
C
H H H C D H C Br
H H
this carbon atom carries major product minor product
more hydrogen atoms
of hydrogen atoms.
this carbon atom carries
more hydrogen atoms
I
I
HI(g)
+
major product minor product
27 D Option D — The rate of hydrolysis of haloalkanes is related to how easily the C–X bond breaks. As the
C–I bond is weaker than the C–Br and C–Cl bonds, the C–I bond breaks most readily. Hence
the rate of hydrolysis of Z is the highest.
As the C–Cl bond is the strongest, the bond is the most difficult to break. Hence the rate
of hydrolysis of X is the lowest.
28 C Options A, B and D — Br2

Cl OH (in organic Br
NaOH(aq) conc. H2SO4 solvent)
X
heat heat
substitution dehydration addition Br

80
29 B Option B — OH Br
dehydration addition

Br
X
cyclohexene

30 D Options A, B and C — These compounds contain NO chiral centres. They have NO enantiomers.
H3C CH3
C C
H3C CH3
H CH2CH2CH2CH3
C C
H H
CH3
H CH2CHCH3
C C
H
H chiral carbon CH3
Option D — This compound contains 1 chiral centre. It has aH pair of enantiomers.

CHCH2CH3
chiral carbon CH3 C C
H H
H CHCH2CH3
C C
H H CH3

Upon hydrogenation, this compound forms CH3CH2CHCH2CH3 , which has NO chiral
centre. CH3
31 C Options A andCH
C 3CH
— 2Propan-1-ol
CHCH2CH3 reacts with phosphorus pentachloride according to the following
equation:
CH3CH2CH2OH + PCl5 CH3CH2CH2Cl + POCl3 + HCl
propan-1-ol 1-chloropropane
Hydrogen chloride fumes are given off.

Option D — A substitution reaction occurs.
32 C Option B — The compound is NOT propene as it cannot decolorize aqueous bromine.

Option C — The compound is propan-1-ol as it is oxidized by acidified potassium permanganate solution. The
purple permanganate ions are reduced to colourless manganese(II) ions in the process.
OH O OH O
33 D Option D — is a secondary alcohol. It undergoes oxidation to produce a ketone, .
81
H H H H
H C C C C H
H OH H H
34 D Option A — Butane-1-ol and butan-2-ol have the same molecular formula (C4H10O).
chiral carbon
Options B and D — Butane-2-ol is a secondary alcohol. When heated under reflux with acidified
( )

H O H H
H C C C C H

potassium dichromate solution, it produces a ketone H H H .
Option C — Butan-2-ol contains 1 chiral carbon. It has a pair of enantiomers.
H H H H
H C C C C H
H OH H H
chiral carbon
35 C Option C — The alcohol undergoes dehydration in the reaction.
( )
H O H H
H CH3 H
H CH3
H C C C C H
dehydration
H C C C CH3 C C
H H H
H C2H5
H OH H
product X
mirror product
remove
H CH3 H
CH3 H
dehydration
H C C C CH3 C C
CH3 CH3
H OH H
product Y
major product
remove
Product X has two alkyl groups attached to the carbon atoms of the C=C bond while
product Y has three. Product Y is the more highly substituted alkene and hence the major
product.
( )
CH3
CH3 C CH3
36 C Options A and D — Methylpropan-2-ol OH is a tertiary alcohol. It resists oxidation.

Option B — Methylpropan-2-ol contains NO chiral carbon. It is optically inactive.
H CH3 H H CH3 H
20% H2SO4
82 H C C C H H C C C H + H2O
85 °C
H OH H H
( )
CH3
CH3 C CH3
Option C — Tertiary alcohols are usually so easily dehydrated that extremely mild conditions can be used.
OH
Methylpropan-2-ol dehydrates in 20% sulphuric acid at a temperature of 85 °C.
H CH3 H H CH3 H
20% H2SO4
H C C C H H C C C H + H2O
85 °C
H OH H H
methylpropan-2-ol methylpropene
37 D Option A — Propanal can be prepared by the oxidation of propan-1-ol.

Propanone can be prepared by the oxidation of propan-2-ol.
Option D — Propanal undergoes oxidation to form propanoic acid when warmed with acidified potassium
dichromate solution. The orange dichromate ions change to green chromium(III) ions in the
process.
Propanone resists oxidation.
Step 1 Step 2
38 B Option B — C H COOH C4H9OH C4H9Cl
3 7
reduction substitution
39 D Option D — O

C O CH3
this part this part comes

comes from from CH3OH
COOH
40 D Option A — Mevalonic acid contains only 1 chiral carbon.

OH
OH
HOOCCH22C(CH
HOOCCH C(CH33)CH
)CH22CH
CH22OH
OH
chiral
chiral carbon
carbon
Option B — Mevalonic acid contains 1 tertiary alcohol group and 1 primary alcohol group.
OH tertiary alcohol group
HOOCCH2C(CH3)CH2CH2OH primary alcohol group

Option D — Mevalonic acid is both an alcohol and a carboxylic acid. Thus, it undergoes esterification
with ethanoic acid and ethanol separately.
83
41 C Option C — O
H3C C O CH2CH2CH(CH3)2
this part this part comes from

comes from (CH3)2CHCH2CH2OH
CH3COOH
– +
Thus, the ester gives CH3COO Na and (CH3)2CHCH2CH2OH on alkaline hydrolysis.
O
42 C Option A — OO
H C O C(CH3)3
HH CC OO C(CH33))33
C(CH
this part this part comes
this
this part from
part
comes thisfrom
this partcomes
part comes
(CH 3)3COH,
comes from
comesHCOOH from
from froma (CH (CH )3)3COH,
tertiary
33
COH,
alcohol
HCOOH aatertiary
HCOOH tertiaryalcohol
alcohol
Thus, this ester gives a tertiary alcohol on hydrolysis.
O
Option C — OO
(CH3)2CH O C C2H5
(CH33))22CH
(CH CH OO CC CC22HH55
this part comes this part
this
this part(CH
part
from comes
comes this
3)2CHOH,this
part from
part
comes
from
from (CH ) CHOH,
(CH33)22CHOH,
a secondary comes
comes
alcohol C2H from
from
5COOH
a secondary alcohol C
a secondary alcohol C22H55COOHH COOH
Thus, this ester gives a secondary alcohol on hydrolysis.
Option D — O
OO
(CH3)2CHCH2 O C CH3
(CH33))22CHCH
(CH CHCH22 OO CC CH33
CH
this part comes from this part
thispart
this part
(CHcomescomes
3)2CHCH
from
from
2OH,
this
this part from
part
comes
(CHa33)2)primary
(CH CHCH22OH,
CHCH
2 OH,
alcohol comes
comes from
CHfrom
3COOH
aaprimary
primaryalcoholalcohol CH33COOH
CH COOH
Thus, this ester gives a primary alcohol on hydrolysis.
43 C Option A — Chain isomers are isomers that have the same functional groups but different carbon
skeletons.
The ester and pentanoic acid have the same molecular formula (C5H10O2) but different
functional groups. Thus, they are NOT chain isomers. Actually, they are functional group
isomers.
Option B — The ester and ethyl propanoate have the same molecular formula (C5H10O2) and functional
group. Thus, they are NOT functional group isomers.
84
Option C — O
CH3 C O CH CH3
CH3 H
this part comes from CH3 C CH3
OH
This ester gives CH3CH(OH)CH3 on hydrolysis. The same alcohol can be formed by the acid-
catalyzed hydration of propene.
acid catalyst
CH3CH=CH2 + H2O CH3CH(OH)CH3
Option D — The ester gives CH3CH(OH)CH3 on hydrolysis. This alcohol can be oxidized by acidified
potassium dichromate solution.
44 B Option B — Compound X gives HCl fumes with PCl5. It probably contains a –OH group.
Compound X gives NH3 when heated with NaOH(aq). It is probably an amide.
O O
R C NH2 + OH– R C O– + NH3
Thus, compound X could be HOCH2CONH2.
45 A Option A — Compounds X, Y and Z in palm oil diesel are esters.

O
CH3O C R
this part comes

from methanol
Thus, the compounds are called methyl esters.
46 C Option C — CH (CH ) CH SO3–K+

3 2 8 2
hydrophobic hydrophilic
47 B Option B — Soapless detergents do NOT increase the hardness of water.
Option C — Soapless detergents often contain phosphate salts as ‘builders’. When the phosphates go into
rivers and seas, they become the nutrients of algae. As a result, algae growth will increase
rapidly.
Option D — Bacteria use up oxygen in the water during the decomposition of soapless detergents.
85
48 A Option A — The biodegradable polymer is made by condensation polymerization of lactic acid
(HOCH(CH3)COOH) and glycolic acid (HOCH2COOH).
Each of these acid molecules has an acid functional group and an alcohol functional group
at the ends. During the formation of the polymer, the acid and alcohol functional groups at
both ends of the acid molecules react to form ester linkages, releasing water molecules.
H2O H2O H2O H2O H2O

O CH3 O O CH3 O
...... + H O CH2 C O H+H O CH C O H +H O CH2 C O H+H O CH C O H + ......
O CH3 O O CH3 O
O CH2 C O CH C or CH2 C O CH C O
n n
49 B
50 D Option D — Concentrated phosphoric acid reacts with sodium iodide to produce hydrogen iodide.
H3PO4 + NaI NaH2PO4 + HI
Butan-1-ol undergoes substitution in the reaction.
C4H9OH + HI C4H9I + H2O
51 B (1) Concentrated phosphoric acid reacts with sodium iodide to produce hydrogen iodide. It is NOT a
catalyst.
(3) Concentrated sulphuric acid is NOT used because it oxidizes iodide ions to iodine and produces very
little hydrogen iodide.
52 A Option B, C and D — CH3 COOH COOCH3
Step 1 Step 2
oxidation esterification
Step 4
PET
CH3 COOH COOCH3 polymerization
Step 3
H2C CH2 HOCH2CH2OH
addition
Thus, dehydration is NOT involved in the synthetic route.
53 C (1) Step 1 involves oxidation.

LiAIH4 / ethoxyethane would bring about a reduction.
86
54 C Functional group isomers are isomers that have the same molecular formula but contain different functional
groups.
(1) CH3CH2CHBrCH3 and CH3CH2CH2CH2Br have the same functional group. They are NOT functional
group isomers.
(2) CH3CH2COOH and HCOOCH2CH3 have the same molecular formula but different functional groups
(–COOH group and –COO– group). Thus, they are functional group isomers.
(3) CH3CH2OCH2CH3 and CH3CH(OH)CH2CH3 have the same molecular formula but different functional
groups (–O– group and –OH group). Thus, they are functional groups isomers.
55 D All the compounds contain 1 chiral carbon and thus can exist enantiomerism.
(1) H H H CH33 H H
H H H CH3 H H
H C C C C C C H
H C C C C C C H
H H H H H H
H H H H H H
chiral carbon
chiral carbon
(2) H H H Br H
H H H Br H
H C C C C C H
H C C C C C H
H H H H H
H H H H H
chiral carbon
chiral carbon
(3) H H CH33 O
H H CH3 O
H C C C C H
H C C C C H
H H H
H H H
chiral carbon
chiral carbon
56 A (1) This molecule has 3 chiral carbons.
CH3 CH2
chiral carbon
CH3
C
CH3
O
chiral carbon
chiral carbon
CH3 CH2
CH3
C
CH3
O
87
carbonyl group
CH3
O
chiral carbon
chiral carbon
(2) This molecule contains a carbonyl group.
CH3 CH2
CH3
C
CH3
O
carbonyl group
(3) This molecule does NOT contain a phenyl group. Thus, it is NOT an aromatic compound.
57 C (1) Rotating the first molecule about the C–COOH bond produces the second molecule.
Br
COOH
Br C
COOH CN
C H
H Br
COOH Br
C COOH
C CN H CN
H C
Br

C
Thus, the two moleculesHare identical. H COOH CN
CN Br
(2) The mirror image of the first molecule is shown below: COOH
BrCN Br
Br C Br C
CN NC
H3C CH3
Br Br
C H H
C
CN NC
H3C NJSSPS CH3
C CN NCH C
H3C H CH3
H NJSSPS H

NJSSPS
The first molecule and its mirror CN
Br image are not superposable.
Rotating the mirror image about the C–Br bond produces the second molecule.
Br C CN C
NC CH3
CH3 H
Br CN
H
C C Br
NC CH3
CH3 H
C C
NC H CH3
CH3 H Br
H CH3 CHBr3

Thus, the two molecules are enantiomers.
CH3C CH3C
H COOH HOOC H
CH3 CH3
C NH2 HC2N
H COOH HOOC H
NJSSPS
C C
H NH2 COOH HOOC H2N H
NH2 NJSSPS H2N
88 NJSSPS
CH3 COOH COOH
C C
NC CH3
C CH3 H C
NC CH3
H CH3 H
Br
H moleucle is shown below:
(3) The mirror image of the first Br
CH3 CH3
CH3 CH3
C C
H COOH HOOC H
C C
H COOH HOOC H
NH2 H2N
NH2 NJSSPS H2N
NJSSPS
CH3 COOH COOH
CH3 COOH COOH
C C C
COOH H H NH2
C NH2 C H3C C
COOH H H NH2
H2N NH2 CH3 H3C H
H2N CH3 H

Thus, the two molecules are enantiomers.
58 B (1) The molecular formulae of the 2-chlorobutanes are C4H935Cl and C4H937Cl. Thus, they have
different molecular masses.
(2) The two 2-chlorobutanes are enantiomers. Thus, they have different effect on a beam of plane
polarized light.
(3 The two 2-chlorobutanes are enantiomers. Thus, they have the same chemical properties unless
the reaction counterpart is optically active.
59 C (1) The two compounds are structural isomers, NOT geometrical isomers.
(2) Both compounds undergo addition reaction with acidified dilute potassium permanganate solution.
(3) Compound X reacts with HBr(g) to give 2-bromobutane.
H CH3 H CH3
H H3
CH CH3
+CHBr C +HHBr C H3H
C C C H
C C 3C C
H3C HH3C H
H Br H Br
compound X compound X 2-bromobutane 2-bromobutane
Compound Y reacts with HBr(g) to give 2-bromobutane as the major product.

H H H H H H H H
H H H H
C C + C
HBr C +C HBr
2H5 C C C2HH5 + CC2H5 C C H +C C2HH5 C C H
C2H5 CHH
2 5 H
Br H Br H H Br H Br
major product major product

minor product minor product
2-bromobutane 2-bromobutane
more hydrogen atoms
more hydrogen atoms
89
( )(
H CH3 H
)
H CH3 H
H C C C OH
H C C C OH
H H H
60 B Compound X gives methylpropan-1-ol H H H when it undergoes hydrolysis. Thus,
H CH3 H
H CH3 H
H C C C Br
H C C C Br
its structure is H H H .
H H H
(1) Compound X has NO chiral carbon. It is achiral.
(2) Compound X and 1-bromobutane have the same molecular formula (C4H9Br), but their atoms are
linked in different orders. They are structural isomers.
(3) The addition of HBr to but-2-ene gives CH3CH2CHBrCH3, NOT compound X.
CH3CH=CHCH3 + HBr CH3CH2CHBrCH3
61 D (1) Compound X undergoes addition reaction with aqueous bromine.

(2) Compound X contains a –OH group. Thus, it gives hydrogen chloride fumes when mixed with
phosphorus pentachloride.
(3) Compound X is oxidized when heated with acidified potassium dichromate solution. The
dichromate solution turns from orange to green in the process.
62 A (1) Compounds X and Y have the same molecular formula (C4H10O), but their atoms are linked in
different orders. They are structural isomers.
(2) Compound X is oxidized when warmed with acidified potassium dichormate solution. The
dichromate solution turns from orange to green in the process.
Compound Y resists oxidation.
(3) Compound X contains 1 chiral carbon. It is optically active.
CH3CH(OH)CH2CH3
chiral carbon
Compound Y contains NO chiral carbon. It is optically inactive.
63 A (1) and (2) Jasmone undergoes addition reaction with acidified dilute potassium permanganate solution
and aqueous bromine. Thus, these reagents show a colour change with jasmone.
(3) Jasmone is a ketone. It resists oxidation. Thus, it would NOT show a colour change with dilute
potassium dichromate solution.
64 D (1) Aspirin contains an ester functional group.
O
COOH
O C CH3

90
O
COOH
O
COOH
O C CH3

(2) Aspirin contains a –COOH group. Thus, it liberates carbon dioxide with sodium carbonate solution.
(3) O
COOH
O C CH3
this part comes from CH3COOH
Ethanoic acid is produced when aspirin is hydrolyzed by acid in the stomach.
65 D (1), (2) and (3)

O O
C CH2CH3
CH2CH3
CH
CH3CH2 O NH2 amine functional group
O NH
C
CH3
oseltamivir

66 A (1) The following carbon compounds are formed when oseltamivir is heated with excess NaOH(aq):
COO–
CH2CH3
CH CH3COO– CH3CH2OH
CH3CH2 O NH2
NH2
67 A The detergent shown is a soapless detergent.

(1) The soapless detergent has a straight hydrocarbon chain. It is biodegradable.
(3) The detergent contains a hydrophobic hydrocarbon ‘tail’ and a hydrophilic anionic ‘head’.
CH3(CH2)10CH2 O S O– Na+
O
hydrophobic
hydrocarbon 'tail'
hydrophilic anionic 'head'
The emulsifying action of the detergent is due to its hydrocarbon ‘tail’ and anionic ‘head’.
68 C (1) Esters, NOT polymeric esters, are used for flavourings and perfumes.
(3) Polymeric esters are formed by condensation polymerization of dicarboxylic acids and diols. Thus,
they are condensation polymers.
91
69 D (1) and (2) Polymer X is formed by condensation polymerization of a diamine and a dicarboxylic acid.
H2O H2O H2O

H O H
H O
H O
N (CH2)6 N C (CH2)4 C
H2O released H O n

Thus, polymer X is a condensation polymer formed from two different monomers.

(3) Polymer X has a great strength because hydrogen bonds exist between its polymer chains.
) 0 ) 0
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70 B (1) and (3) NH CH CO NH CH CO NH CH CO

NH CH CO NH CH CO NH CH CO
CH2 CH2 (CH2)4
CH2 CH2 (CH2)4
OH COOH NH2
OH COOH NH2
The following amino acids are produced by hydrolyzing this segment of protein:
H2N CH COOH H2N CH COOH H2N CH COOH
H2N CH COOH H2N CH COOH H2N CH COOH
CH2 CH2 (CH2)4
CH2 CH2 (CH2)4
OH COOH NH2
OH COOH NH2
71 C Propanoic acid and methyl ethanoate have the same molecular formula (C3H6O2), but their atoms are
linked in different orders. They are structural isomers.
72 D Pentan-3-ol molecule does NOT contain any carbon atom bonded to four different groups of atoms. Thus,
it CANNOT exhibit enantiomerism.
92
73 A In a 2-hydroxybenzaldehyde molecule, due to the close proximity of the –OH group and –CHO group,
intramolecular hydrogen bonds are readily formed. Thus, intermolecular hydrogen bonds between the
molecules are less extensive.
O
H
IZESPHFOCPOE
O
C
74 C An addition reaction occurs when propene reacts with cold alkaline dilute potassium permanganate
solution.
cold alkaline
dilute potassium
permanganate
solution
CH3CH CH2 CH3CHCH2
OHOH
The two –OH groups are added to the adjacent carbon atoms of the double bond.
75 A
76 C Butanone is prepared by the oxidation of butan-2-ol, NOT butan-1-ol.
OH O
C2H5 C H + [O] C2H5 C CH3 + H2O

butanone
CH3
butan-2-ol
77 D The reagent LiAlH4 does NOT affect carbon-carbon double bonds. Hence it can convert unsaturated
aldehydes and ketones into unsaturated alcohols.
O H OH
2 H3O+
cyclohex-2-enone cyclohex-2-enol
78 B Concentrated sulphuric acid acts as a catalyst in the preparation of an ester from an alcohol and a
carboxylic acid.
79 D Both methylpropan-2-ol (a tertiary alcohol) and propanone (a ketone) resist oxidation. There is NO observable
change when each is warmed with acidified potassium dichromate solution.
93
80 A
81 B
82 B Soapless detergents form soluble substances with calcium salt or magnesium salt. Thus, soapless detergents
do not form scum in hard water. They function well in hard water.
83 D Sea water contains a relatively high concentration of magnesium salts. Soap forms scum in sea water.
Thus, soap is UNSUITABLE for treating oil spillage on sea surface.
84 A Grease forms soap when hydrolyzed by an alkali.
85 A Nylon has a great strength because hydrogen bonds exist between its polymer chains.
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86 B Polyesters are thermoplastics. They soften on heating.
87 C Nylon-6,6 is formed by condensation polymerization. It is a condensation polymer.
H2O H2O H2O

H O H
H O
H O
N (CH2)6 N C (CH2)4 C
H2O released H O n
88 A
94
Short questions
89 a) 4-methylpent-2-ene (1)
b) 3-bromobut-1-ene (1)
c) 2-chloro-2-methylhexane (1)
d) pentan-2-ol (1)
e) 2-ethylbutan-1-ol (1)
f) hex-3-enal (1)
g) 3-oxobutanoic acid (1)
h) 4-methylpentan-2-one (1)
i) 2-methylpropyl methanoate (1)
j) 2-aminopropanoic acid (1)
90 a) CH 3 CH3
CH3CHCH2CHCH3 (1)
b) CH3

CH2CH3 (1)
c) O
C
CH3
(1)
d) O
CH 3CH2CH C O CH2CH3
CH3 (1)
e) CH2=CHCONH2 (1)
91 a) functional group isomers (1)
b) chain isomers (1)
c) position isomers (1)
d) position isomers (1)
95
e) functional group isomers (1)
f) functional group isomers (1)
92 a) no (1)
b) yes (1)
c) no (1)
d) no (1)
e) yes (1)
f) yes (1)
93 a) H H H Cl H
H C C C C* C H 2-chloropentane
(1) (1)
H H H H H
b) H H OH H
H C C C* C H butan-2-ol
(1) (1)
H H H H
c) H H CH3 H H
H C C C* C C H 3-methylpent-1-ene
(1) (1)
H H H
d) H H CH3
H C C C* COOH 2-methylbutanoic acid
(1) (1)
H H H
e) H Br
H C C* CHO 2-bromopropanal
(1) (1)
H H
94 a) propane (1)
b) ethanoic acid (1)
c) ethyl ethanoate (1)
d) butanamine (1)
e) cyclohexene (1)
f) butanal (1)
96
95 a) and b)
Type of reaction
Test Observation(s)
involved
Shake a few drops of X with The aqueous bromine changes from yellow-
addition (1)
aqueous bromine. brown to colourless quickly. (1)
Add phosphorus pentachloride

Steamy fumes are observed. (1)
to X. Test any gas evolved with substitution (1)
The moist blue litmus paper turns red. (1)
moist blue litmus paper.
Add acidified potassium

The acidified potassium dichromate solution
dichromate solution to X oxidation (1)
changes from orange to green. (1)
and heat the mixture.
96 a) Any one of the following:
• Add solid sodium hydrogencarbonate (or solution). (1)
X gives a gas that turns limewater milky. (1)
• Use moist blue litmus paper / pH paper for testing. (1)
X turns moist blue litmus paper / turns pH paper orange (or red). (1)
b) Any one of the following:
• Add aqueous bromine. (1)
Y turns aqueous bromine from yellow-brown to colourless quickly. (1)
• Add cold acidified dilute potassium permanganate solution. (1)
Y turns the permanganate solution from purple to colourless quickly. (1)
• Heat with acidified potassium dichromate solution. (1)
Y turns the dichromate solution from orange to green. (1)
97 a) Cl2 / ultraviolet light (1)
b) CH3
(1)
c) red P + I2; reflux (1)
d) conc. H2SO4; heat (1)
97
e)
COOH
(1)
f) CH3CH(OH)CH2CH3 (1)
g) 1 NH3; 2 heat (1)
h) 1 LiAlH4 / ethoxyethane; 2 H3O+ (1)
i) NaOH(aq); heat (1)
j) COOH
OH
(1)
98 a) CH3CH(OH)CH2OH (1)
b) H3CH2C CH2CH3
H3C C C H
Br H (1)
c) H CH2CH3
H C C CH3
D Br (1)
d)
O
(1)
e)
Cl
(1)
f) CH3CH2CH2I (1)
g) CH3
CH 3 C CHCH2CH3 (1)
h) OH
CH3
(1)
i) CH 3CH2O NH2
(1)
+ CH3COO–Na+
(1)

98
99 a) i) H O
C
H C OH
HO C H
H C OH
H C OH

CH2OH (1)
ii) Carbonyl group (1)
Hydroxyl group (1)
b) i) Carboxyl group (1)
ii) H O H O
HO C C N C C OH
CH3 H CH3 (1)
H O H O
H2N C C O C C OH

CH3 CH3 (1)
iii) Any one of the following:
• Peptide link / amide functional group (1)
• Ester functional group (1)
Structured questions
100 a) H H H H CH3 CH3

C CH2 C C C C C CH2
CH3CH2 (1) CH3 CH3 (1) CH3 H (1) CH3 (1)
b) i) H H H CH3
C C and C C are cis-trans isomers.
CH3 CH3 CH3 H
(1)
99
ii) In order for the intermolecular forces to work well, the molecules must be able to pack together
efficiently in the solid. (1)
Molecule of the trans isomer has a more regular and symmetrical structure than molecule of the cis
isomer. (1)
Molecules of the trans isomer can pack more compactly in the solid.
More heat is required to overcome the intermolecular forces between the molecules. (1)
Hence the trans isomer has a higher melting point than the cis isomer.
101 a) 2-hydroxybenzaldehyde (1)
b) Position isomerism (1)
c) X can form intramolecular hydrogen bonds. (1)
Y forms more intermolecular hydrogen bonds than X does. (1)
Thus the melting point of Y is much higher than that of X.
102 a) Any one of the following:
• Warm each compound with acidified potassium dichromate solution. (1)
A turns the dichromate solution from orange to green. (1)
There is no observable change for B. (1)
• Warm each compound with acidified potassium permanganate solution. (1)
A turns the purple permanganate solution colourless. (1)
There is no observable change for B. (1)
b) Put a mixture of about 2 cm3 of ethanol and 1 cm3 of silver nitrate solution in each of two test tubes. (1)
Place the test tubes in a water bath at 60 °C. (1)
Add several drops of C and D separately to each test tube.
A yellow precipitate forms rapidly in the test tube containing D. (1)
A white precipitate forms slowly in the test tube containing C. (1)
c) Warm each compound with acidified potassium dichromate solution. (1)
F turns the dichromate solution from orange to green. (1)
There is no observable change for E. (1)
d) Add aqueous bromine to each compound separately. (1)
G decolorizes aqueous bromine quickly. (1)
There is no observable change for H. (1)
100
103 a) i) hydroxyl group (1)
ii) carbonyl group (1)
iii) carboxyl group (1)
b) 1 LiAlH4 / ethoxyethane (1)
2 H3O+ (1)
c) Excess concentrated sulphuric acid (1)
180 °C (1)
d) V (1)
K2Cr2O7 / H3O+ (1)
e) Any one of the following:
• Warm each compound with acidified potassium dichromate solution. (1)
U turns the dichromate solution from orange to green. (1)
There is no observable change for Y. (1)
• Mix each compound with phosphorus pentachloride. (1)
U gives steamy fumes of hydrogen chloride. (1)
There is no observable change for Y. (1)
f) Heat V and Z under reflux in the presence of concentrated sulphuric acid. (1)
O CH3
CH 3CH2CH2C O CHCH2CH3 (1)
g) V (1)
*
CH2CH(OH)CH2CH3 (1)
104 a) i) Condenser (1)
ii) Compound X is flammable. (1)
iii) To ensure even boiling. (1)
iv) Propanoic acid (1)
[O]
v) CH3CH2CH2OH CH3CH2COOH (1)
vi) As an oxidizing agent (1)
101
vii)
UIFSNPNFUFS
XBUFSPVU
DPOEFOTFS
SFBDUJPONJYUVSF
BOUJCVNQJOH
HSBOVMFT XBUFSJO
HFOUMFIFBU
BRVFPVTTPMVUJPO
PGQSPQBOPJDBDJE
(1 mark for a correct set-up; 1 mark for correct labels; 1 mark for the correct direction of water flow
in condenser; award 0 mark if the set-up is not workable) (3)
b) i) Ethyl propanoate (1)
ii) As a catalyst (1)
iii) Heating under reflux can reduce the loss of volatile reactants / products by evaporation. (1)
105 a) i) substitution (1)
ii) dehydration / elimination (1)
iii) addition (1)
b) i) Cl2 (1)
ultraviolet light / sunlight (1)
ii) sodium hydroxide solution (1)
reflux / heat (1)
iii) excess concentrated sulphuric acid (1)
180 °C (1)
c) i) Structural isomers are compounds with the same molecular formula, (1)
but differ in the order in which atoms are linked. (1)
102
ii) and iii) Alcohol Classification
primary
CH3CH2CH2CH2OH (0.5)
OH
secondary
CH3CH2CHCH3 (0.5)
CH3
primary
CH3CHCH2OH
(1) (0.5)
CH3
CH3COH tertiary
CH3 (1) (0.5)
d) Any one of the following:
• HCl(g) (1) in the presence of ZnCl2 catalyst (1)
• reflux with concentrated hydrochloric acid (1) using ZnCl2 as catalyst (1)
• reflux (1) with sulphur dichloride oxide (1)
• mix (1) with phosphorus pentachloride (1)
e) i) Dehydration (1)
ii) CH3CH=CHCH3 (1)
106 a) Carbon-carbon double bond (1)
Hydroxyl group (1)
b) H CH3
H C C CH2CH2OH 3-methylbutan-1-ol
H H (1) (1)
H CH3
H C C CH2CH2OH 3,4-dibromo-3-methylbutan-1-ol
Br Br (1) (1)

103
c) i) 3-methylbut-3-enoic acid (1)
ii) Heat under reflux (1)
with acidified potassium dichromate solution (1)

iii) H CH3
C C or 3-methylbut-3-enal (1)
H CH2CHO
d) H CH3
H CH3
C C + 2HBr (1) H C C CH2CH2Br + H2O (1)
H CH2CH2OH
H Br
107 a) H H
H C C Br

H H (1)
b) i) Heat under reflux (1)
with acidified potassium dichromate solution (1)
ii) React with aqueous ammonia to form an ammonium salt. (1)
Evaporate the water and subsequently heat the dry salt. (1)
c) i) Substitution (1)
ii) Oxidation (1)
iii) Reduction (1)
d) CH3COOH > CH3CH2OH > CH3CH2NH2 (1)
The boiling point of a compound depends on its molecular attractions. (1)
All the compounds can form hydrogen bonds.
Molecules of CH3COOH can form more extensive hydrogen bonds than those of CH3CH2OH. (1)
Thus the boiling point of CH3COOH is higher than that of CH3CH2OH.
Since oxygen is more electronegative than nitrogen, the O–H bond in CH3CH2OH is more polar than the
N–H bond in CH3CH2NH2.
As a result, stronger hydrogen bonds exist between molecules of CH3CH2OH. (1)
Thus the boiling point of CH3CH2OH is higher than that of CH3CH2NH2.
104
108 a) Carbon-carbon double bond (1)
Carbonyl group (1)
b) i) Stereoisomers have their atoms linked in the same way, (1)
but they differ in the spatial arrangement of their atoms. (1)
ii) Geometrical isomerism (1)
iii) Due to the restricted rotation about a carbon-carbon double bond. (1)
iv) Identical methyl groups attach to one of the carbon atoms of the C=C bond. (1)
c) i) (H3C)2C CHCH2CH2C CHCH2OH
CH3 (1)
ii) Primary alcohol (1)
There is one alkyl group attached to the carbon bearing the –OH group. (1)
iii) 1 LiAlH4 / ethoxyethane
2 H3O+ (1)
iv) (1) O
(H3C)2C CHCH2CH2C CHCH2 O C CH3
CH3 (1)
(2) Esterification (1)
109 a) CH3

CH3 CHCH
2Br (1)
b) CH3

CH3 C CH2 (1)
methylpropene (1)
c) i) CH3

CH3CBrCH3 (1)
2-bromo-2-methylpropane (1)
ii) Structural isomers are compounds with the same molecular formula, (1)
but differ in the order in which atoms are linked. (1)
iii) CH3CH2CH2CH2Br (1)
CH3CH2CHBrCH3 (1)
105
110 a) H H H
C C C H
Br Br H (1)
b) X, Y and Z are formed from the dehydration of alcohol W.
Thus they are alkenes. (1)
H H H
X and Y react with bromine to give 1,2-dibromo-1-phenylpropane, i.e. C C C H .
Br Br H
It can be deduced that the structures of X and Y are as follows:
H H H CH3
C C C C
CH3 H
(1) (1)
H H H
Z reacts with bromine to give 2,3-dibromo-1-phenylpropane, i.e. C C C H .
H Br Br
It can be deduced that the structure of Z is as follows:

H H H
C C C H
H (1)
W undergoes dehydration to give X, Y and Z. It can be deduced that the structure of W is as follows:
H H H
C C C H
H OH H (1)
c) X and Y exhibit geometrical isomerism. (1)
X, Y and Z exhibit structural / position isomerism. (1)
d) i) The purple permanganate solution becomes colourless quickly. (1)
ii) H H H
C C C H
OH OH H (1)
106
111 a) i) Suppose we have 100 g of compound X, so there are 40.0 g of carbon, 6.65 g of hydrogen and
53.3 g of oxygen.
Carbon Hydrogen Oxygen

Mass of
element
40.0 g 6.65 g 53.3 g
in the
compound
Number of
moles of 40.0 g 6.65 g 53.3 g
= 3.33 mol = 6.65 mol = 3.33 mol (1)
atoms that 12.0 g mol–1 1.0 g mol–1 16.0 g mol–1
combine
Simplest
3.33 mol 6.65 mol 3.33 mol
ratio of = 1 = 2 = 1 (1)
3.33 mol 3.33 mol 3.33 mol
atoms
∴ the empirical formula of X is CH2O.
ii) Let (CH2O)n be the molecular formula of X.
Relative molecular mass of X = n(12.0 + 2 x 1.0 + 16.0)

= 30n
i.e. 30n = 90.0
n = 3
∴ the molecular formula of X is C3H6O3. (1)
b) Effervescence occurs when X is mixed with sodium hydrogencarbonate solution. Thus it should be a
carboxylic acid and contain a –COOH group. (1)
X undergoes esterification with ethanoic acid. Thus it should contain a –OH group. (1)
X is chiral. Thus it should contain at least one chiral carbon. (1)
Structure of X: H OH O
H C C C OH
H H chiral carbon (1)

2-hydroxypropanoic acid (1)
c) H O O
H C C C OH
H (1)
107
d) O
CH3 C
C O
H H
O C
C CH3
O (1)
Ester functional group (1)
112 Since W can be hydrolyzed to give an acid X and a neutral compound Y, so W should be an ester. (1)
Relative molecular mass of W = 10 x 12.0 + 12 x 1.0 + 2 x 16.0 = 164.0
Relative molecular mass of Y = 164.0 + 18.0 – 122.0 = 60.0 (1)
Let the molecular formula of Y be CnH2n+1OH.
i.e. 12n + 2n+1 + 16.0 + 1.0 = 60.0

n = 3
∴ the molecular formula of Y is C3H7OH (1) and that of X is C7H6O2 or C6H5COOH. (1)
COOH
The structure of X is . (1)
Y can be oxidized to Z, so Z should be an aldehyde or a ketone.
As Z does not react with acidified potassium dichromate solution, thus Z should be a ketone. (1)
Z is propanone, CH3COCH3. (1)

OH
∴ Y is a secondary alcohol, CH3CHCH3 . (1)
COOCH(CH3)2
W is . (1)
NaOH(aq)
113 a) CH3CH2CH2CH2Br CH3CH2CH2CH2OH
reflux
(1) (1)
+
K2Cr2O7 / H3O
CH3CH2CH2COOH
reflux
(1)
108
b) CH2CH2OH conc. H2SO4 CH CH2
heat
(1) (1)
HBr(g) CHBrCH3 NaOH(aq) CH(OH)CH3

reflux
(1) (1) (1) (1)
K2Cr2O7 / H3O+ CCH3

reflux
(1)
c) conc. H2SO4
CH3CHCH3 CH3CH CH2
heat
(1) (1)
OH
cold alkaline
CH3CHCH2OH
dilute KMnO4
(1) OH
d) CH2CH2Br NaOH(aq) CH2CH2OH K2Cr2O7 / H3O+ CH2COOH
reflux reflux
(1) (1) (1) (1)
CH2COOCH3
CH3OH / conc. H2SO4
heat
(1)
e) H3O+ 1 LiAlH4 / ethoxyethane

CH2CONH2 CH2COOH CH2CH2OH
heat 2 H3O+
(1) (1) (1)
f) Cl NaOH(aq) OH conc. H2SO4 or conc. H3PO4
reflux heat
(1) (1) (1) (1)
Br
Br2 (in organic solvent)
(1) Br
109
114 a) Pressure builds up in the set-up when the mixture is heated. It was dangerous to conduct an experiment
using a closed system. An explosion may occur. (1)
Modification – add a receiver adaptor between the condenser and the round-bottomed flask. (1)
b) i) Use a teat pipette to remove the bottom layer. / Use a separating funnel and run off the bottom
layer. (1)
ii) To dry the organic layer. (1)
iii) Any one of the following:
• Add aqueous bromine to the distillate. (1)
The yellow-brown aqueous bromine changes to colourless quickly. (1)
• Add cold acidified dilute potassium permanganate solution to the distillate. (1)
The purple permanganate solution changes to colourless quickly. (1)
iv) • Add phosphorus pentachloride to the distillate. (1)
• Steamy fumes would be observed. (1)
115 a) The process is exothermic. (1)
b) i) To remove the excess dilute sulphuric acid. (1)
ii)
BRVFPVTMBZFS
CSPNPQSPQBOFMBZFS
(1 mark for correct drawing of separating funnel with tap; 1 mark for showing 1-bromopropane
layer on bottom; award 0 mark if the funnel is not workable) (2)
iii) To prevent pressure building up due to the formation of carbon dioxide gas. (1)
c) To dry the product. (1)
d) Use an electric heating mantle / a water bath / an oil bath for heating (1)
because propan-1-ol / 1-bromopropane is flammable. (1)
110
e) i) UIFSNPNFUFS
XBUFSPVU
TUJMMIFBE
DPOEFOTFS
GSBDUJPOBUJOH
DPMVNO
SFDFJWFS
HMBTTCFBET BEBQUPS
XBUFSJO
PSHBOJD
BOUJCVNQJOH
MBZFS EJTUJMMBUF
HSBOVMFT
IFBU
(1 mark for correct set-up; 1 mark for correct labels; 1 mark for correct drawing of fractionating
column; 1 mark for correct direction of water flow in condenser; award 0 mark if the set-up is not
workable) (4)
ii) 70 °C – 72 °C (1)
9.12 g
f) i) Number of moles of propan-1-ol = –1
60.0 g mol
= 0.152 mol
According to the equation, 1 mole of propan-1-ol gives 1 mole of 1-bromopropane.
Theoretical yield of 1-bromopropane = 0.152 mol x 122.9 g mol–1

= 18.7 g (1)
10.8 g
Percentage yield of 1-bromopropane = x 100%
18.7 g
= 57.8% (1)
ii) Any one of the following:
• The reaction is incomplete. (1)
• Some of the propan-1-ol dehydrate to form an alkene. (1)
• Some of the product stay in the aqueous layer. (1)
116 a) Methanol (1) and propanoic acid (1)
b) As a catalyst (1)
c) CH3OH(l) + CH3CH2COOH(l) CH3CH2COOCH3(l) + H2O(l) (1)
d) H H O H
H C C C O C H
H H H (1)
111
e) Methanol is flammable and it catches fire easily. (1)
f) Any two of the following:
A pleasant smell could be detected. (1) / An insoluble layer formed on the sodium carbonate solution.
(1) / Effervescence occurred. (1)
g) B (1)
h) Any one of the following:
O O
H C OCH2CH2CH3 (1) propyl methanoate (1) CH3 C OCH2CH3 (1) ethyl ethanoate (1)
O
H C OCH(CH3)2 (1) methylethyl methanoate (1)
i) Any one of the following:
H H H O
H C C C C OH
H H H (1) butanoic acid (1)
H CH3 O
H C C C OH
H H (1) methylpropanoic acid (1)
117 a)
XBUFSPVU
SFGMVYDPOEFOTFS
XBUFSJO
NJYUVSFPGFUIZM
BOUJCVNQJOH
CFO[PBUFBOE
HSBOVMFT
FYDFTT/B0) BR
IFBU
(1 mark for correct set-up; 1 mark for correct direction of water flow in condenser; award 0 mark if the
set-up is not workable) (2)
b) To prevent any loss of the volatile substance / ester by evaporation. (1)
c) To convert sodium benzoate into benzoic acid. (1)

112
d) Dissolve the crude sample in minimum amount of hot water. (1)
Filter the mixture while hot. (1)
Allow the filtrate to cool and collect the crystals by filtration. (1)
4.50 g
e) i) Number of moles of ethyl benzoate = –1
150.0 g mol
= 0.0300 mol
According to the equation, 1 mole of ethyl benzoate gives 1 mole of benzoic acid on hydrolysis.
Theoretical yield of benzoic acid = 0.0300 mol x 122.0 g mol–1

= 3.66 g (1)
2.29 g
Percentage yield of benzoic acid = x 100%
3.66 g
= 62.6% (1)
ii) Hydrolysis is not complete. / Benzoic acid is slightly soluble in water. (1)
118 a) 3-methylbutyl ethanoate (1)
b) (CH3)2CH(CH2)2OH (1)
3-methylbutan-1-ol (1)
c) Reagent Y is concentrated sulphuric acid. (1)
Heat the reaction mixture under reflux. (1)
d) Esterification (1)
e) Any two of the following:
• Isoamyl acetate (1)
• Acetic acid (1)
• Water (1)
f) • Shake the mixture with sodium hydrogencarbonate solution until no more gas is evolved. (1)
• Extract the isoamyl acetate from the mixture using ethoxyethane. (1)
• Remove the ethoxyethane by simple distillation. (1)
119 a) i) Cause bleeding in the stomach lining (1)
ii) Paracetamol (1)
b) i) 2-hydroxybenzoic acid (1)
ii) Heat with methanol (1)
and a little concentrated sulphuric acid. (1)
iii) COO–Na+

OH (1) 113
8.28 g
c) Number of moles of salicylic acid used = –1
138.0 g mol
= 0.0600 mol (1)
7.20 g
Number of moles of aspirin obtained = –1
180.0 g mol
= 0.0400 mol (1)
0.0400 mol
Percentage conversion = x 100%
0.0600 mol
= 66.7% (1)
d) To show the presence of the –COOH group, add sodium hydrogencarbonate solution to the
compound. (1)
Evolution of colourless gas bubbles indicates the presence of the –COOH group. (1)
To show the presence of the ester group, heat the compound with dilute acid. (1)
Smell of vinegar is noted. (1)
e) i) Ca(OH)2 (1)
ii) Aspirin is a covalent compound with intramolecular hydrogen bonds. This reduces the extent of
hydrogen bonding with water, thus making aspirin insoluble in water. (1)
The large hydrophobic benzene ring also leads to low water solubility. (1)
The calcium salt is ionic. Strong interactions exist between water and the ions. (1)
120 a) Saponification (1)
b) O
H2C O C C17H33 H2C OH

O
HC O C C17H33 + 3NaOH HC OH + 3C17H33COO–Na+

O
H2C O C C17H33 H2C OH (2)
c) Label C (1)
• Wear safety glasses. (1)
• Wear protective gloves. (1)
e) To lower the solubility of soap in water. (1)
f) To prevent the soap from dissolving in the water. (1)
114
g) Perfume (1) and colouring (1)
h) Not suitable (1)
Sea water contains a lot of magnesium ions and calcium ions. The soap would react with the metal ions
to form scum and thus reduce the cleaning effectiveness of soap. (1)
121 a) Any two of the following:
• Hydrocarbons obtained from petroleum (1)
• Concentrated sulphuric acid (1)
• Sodium hydroxide (1)
b) i) O
O S O–
O (1)
ii) CH3(CH2)10CH2 — (1)
c) When mixed with a mixture of water and paraffin oil, the hydrophobic parts of the detergent particles
dissolve in the oil while the hydrophilic parts dissolve in water. (1)
Upon shaking, oil droplets form. Each drop is surrounded by detergent particles with the hydrophilic parts
in the water. (1)
The hydrophilic parts carry negative charges and prevent the oil droplets from coming together again.
Hence an emulsion is formed. (1)
d) Detergent X can emulsify the crude oil into droplets and (1)
the droplets can be carried out away by water currents. (1)
e) i) Yes (1)
ii) During the decomposition of the detergent, bacteria use up oxygen in the water. This makes the water
smell badly due to oxygen depletion. (1)
f) i) Calcium ion (1)
Magnesium ion (1)
ii) Detergent X can function well in hard water (1)
because it does not form scum with hard water. (1)
122 a) i) Carboxyl group (1)
ii) Hydroxyl group (1)
b) Sodium hydroxide solution (1)
115
c) O O
C C O CH2 CH2 O
(1)
d) Condensation polymerization (1)
e) Permanent dipole-permanent dipole attractions between PET polymer chains are stronger (1)
than the instantaneous dipole-induced dipole attractions between polythene polymer chains. (1)
f) i) Hydrolysis (1)
ii) HO CH2 CH2 OH (1)
O O
+ – – +
Na O C C O Na
(1)
123 a i) The molecule of valine contains one carbon atom bonded to four different groups of atoms. (1)
ii)
H H
C COOH HOOC C
(CH3)2HC CH(CH3)2
NH2 H2N
(1) (1)
NJSSPS
iii) (1) Rotation of plane of plane-polarized light (1)
(2) Rotate the plane of plane-polarized light in opposite directions. (1)
b) CH3 O CH(CH3)2
H2N CH C N CH COOH
H (1)
CH(CH3)2 O CH3

H2N CH C N CH COOH
H (1)
116
c) CH3
H N +CHCOOH (1)
3
CH3

H2N CHCOO– (1)
124 a) Amine functional group (1), carboxyl group (1), amide functional group (1), ester functional group (1)
b) O O
* *
H2N CH C NH CH C OCH3
CH2 CH2
CO2H
(2)
c) H O
H2N C C OH
CH2COOH (1)
COOH
H2N CHCH2
(1)
d) Silicon dioxide increases the bulk mass of the sweetener. (1)
e) Phenylketonurics are unable to metabolize the phenylalanine produced from the hydrolysis of
aspartame. (1)
A high level of phenylalanine in the brain is extremely harmful and sometimes fatal. (1)
125 a) Condensation polymerization (1)
b) H
H N (CH2)6 N H
H (1)
H O C (CH2)4 C O H
O (1)
117
c) H O
N (CH2)6 N C (CH2)4 C
H O (1)
Lighter in weight (1)
Does not corrode easily (1)
e) There are hydrogen bonds between the polymer chains of nylon. (1)
Only weak instantaneous dipole-induced dipole attractions exist between the polymer chains of
polythene. (1)
Hence nylon is stronger than polythene.
f) A hole would appear (1)
because the acid hydrolyzes the amide linkages in nylon. (1)
g) Method I:
The waste contains dichromate ions which is toxic. (1)
Method II:
Concentrated nitric acid is a strong acid. Discharge of the waste into waterways leads to environmental
pollution. (1)
126 a) Any two of the following:
Burning fossil fuels produces a lot of air pollutants. (1)
The resources of fossil fuels are limited. (1)
Supply and price of petroleum may become unstable in times of political unstability in petroleum-producing
countries. (1)
Petroleum spills during drilling or transportation cause major damage to ecosystems both on land and at
sea. (1)
b) Burning ethanol returns carbon dioxide (1)
which has been recently removed from the atmosphere during the photosynthesis of plants. (1)
c) More energy can be obtained. (1)
d) Any two of the following:
Farmers use fossil-fuel-powered equipment to plant, maintain and harvest the corn. (1)
Fossil-fuel-powered machines are required to process the corn into ethanol. (1)
Ethanol is transported to collection points via fossil-fuel-powered transport. (1)
118
e) Any one of the following:
This may lead to diversion of investment from food production, resulting in increased food prices. (1)
Ethanal is also produced during the combustion of ethanol. It can harm vegetation, irritate the skin and
eyes, and damage the lungs at high concentrations. (1)
f) As a solvent (1)
127 Any three of the following properties:
Physical properties
• Hydrogen bonds exist between ethanol molecules. (1)
Thus the boiling point of ethanol is higher than those of alkanes / haloalkanes of similar relative molecular
masses. (1)
• Due to the hydrogen bonding between ethanol molecules and water molecules, (1)
ethanol is miscible with water in all proportions. (1)
Chemical properties
• Ethanol reacts with hydrogen halides to form haloethanes. (1)
Bromoethane can be prepared by heating a mixture of ethanol, sodium bromide and concentrated sulphuric
acid under reflux. Concentrated sulphuric acid reacts with sodium bromide to produce hydrogen bromide.
Hydrogen bromide then reacts with ethanol to give bromoethane. (1)
OR
Bromoethane can be prepared by heating a mixture of ethanol, red phosphorus and bromine under
reflux. Phosphorus first reacts with bromine to give phosphorus tribromide. The tribromide then reacts
with ethanol to give bromoethane. (1)
• Ethanol can be dehydrated to form ethene. (1)
This is done by heating ethanol at 180 °C with excess concentrated sulphuric acid / passing ethanol
vapour over aluminium oxide at 300 °C. (1)
• Ethanol can be oxidized to ethanal, and then to ethanoic acid. (1)
This is done by heating ethanol with acidified potassium dichromate solution under reflux. The reflux
condenser prevents any loss of the reaction mixture and favours the oxidation of ethanol to ethanoic acid
rather than to ethanal. (1)
• Ethanol reacts with carboxylic acid in the presence of concentrated sulphuric acid to form an ester. (1)
For example, heating ethanol with methanoic acid in the presence of concentrated sulphuric acid gives
the ester ethylmethanoate. (1)
(3 marks for organization and presentation)
119
128 Add water to the liquids. (1)
Both butanoic acid and propanone can mix with water in all proportions. (1)
Add a piece of pH paper to the aqueous solutions. (1)
Solution of butanoic acid is acidic while that of propanone is not. (1)
Add aqueous bromine to the remaining two compounds. (1)
Only cyclohexene can decolorize the aqueous bromine quickly. (1)
OR
Add a mixture of silver nitrate solution and ethanol to the remaining two compounds. (1)
Only 1-bromobutane gives a pale yellow precipitate slowly. (1)
129 Soaps are mainly made from the reaction between fats (or vegetable oil) and sodium hydroxide
solution. (1)
Soapless detergents are made from hydrocarbons obtained from petroleum, concentrated sulphuric acid and
sodium hydroxide. (1)
Both of them have good cleaning ability in soft water. (1)
However, soaps form scum and lose cleaning ability in hard water while soapless detergents do not. (1)
Branch-chained soapless detergents are non-biodegradable. They form thick foam which prevents oxygen
from dissolving into water and leads to the death of aquatic life. (1)
Soaps and straight-chained soapless detergents are biodegradable. When they are decomposed by bacteria in
rivers or sea, oxygen in water is used up. This leads to oxygen depletion and thus causes death of aquatic
lives. (1)
In general, soaps and straight-chained soapless detergents cause fewer pollution problems than branch-chained
soapless detergents.
120

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Topic 8 Chemistry of Carbon Compounds

Part A Unit-based exercise

Unit 29 An introduction to the chemistry of carbon compounds

Fill in the blanks

7 permanent dipole-permanent dipole attractions

15 T Esters are polar compounds.

Multiple choice questions

19 B Option B — Molecular formula C2H4O2 represents an ester.

21 A Option A — LSD has an amide functional group.

Option A — The compounds belong to different homologous series.

The parent chain contains 5 carbon atoms, i.e. pentane.

The parent chain contains 8 carbon atoms, i.e. octane.

The parent chain contains 4 carbon atoms, i.e. butane.

The parent chain contains 4 carbon atoms, i.e. butane.

The parent chain contains 7 carbon atoms, i.e. heptane.

The parent chain contains 4 carbon atoms, i.e. butane.

40 B Option B — 1CH 2CCH

CH3 CH2 CH2 C O CH2 CH3

this part comes from this part comes

Thus, the IUPAC name of this ester is ethyl butanoate.

CH3 C O CH2 CH CH3

this part comes from this part comes from

Thus, the IUPAC name of this ester is 2-methylpropyl ethanoate.

this part comes from this part comes from

Thus, the IUPAC name of this ester is cyclohexyl ethanoate.

46 C Option C — this part comes from this part comes from

Thus, the IUPAC name of this ester is methyl benzoate.

CH3 O C CH2 CH3

this part comes this part comes

Thus, the IUPAC name of this ester is methyl propanoate.

this part comes from this part comes

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Only instantaneous dipole-induced dipole attractions exist between but-1-ene molecules.

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63 C (1) Amines contains the –NH2 functional group.

(2) Amides contain the C NH2 functional group.

(3) Esters contain the C O functional group.

67 A (1) This compound contains an amide functional group.

amide functional group

68 B (1) and (2) OH

70 D CH3COCH2CH3 is a ketone while CH3CH2CH2CHO is an aldehyde.

(2) Both compounds contain a carbonyl group C .

Fill in the blanks

5 opposite; optically active

CH3 CH3 CH3 H

9 T Cis-butenedioic acid has a net dipole moment.

11 F The boiling point of cis-1,2-dichloroethene is higher than that of trans-1,2-dichloroethene.

13 F Molecule of 3-bromohexane does NOT have a plane of symmetry.

Multiple choice questions

20 C Option C — Three isomers exist for dibromobenzene.

21 D Option D — Four structurally isomeric alcohols have the formula C4H9OH.

25 B Option A — The two compounds are amines, NOT amides.

27 B Option B — The two molecules are geometrical isomers.

C3H7 H C3H7 CH3

Option C — C2H5C CCH2I can exhibit geometrical isomerism.

35 B Option B — Warfarin contains 1 chiral carbon.

36 B Option B — 1,3-dichlorobutane is a chiral molecule.

38 A Option A — The mirror image of the first molecule is shown below:

40 B Option A — The two members are geometrical isomers.

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