Topic 8 Chemistry of Carbon Compounds

Part A Unit-based exercise

Unit 29 An introduction to the chemistry of carbon compounds
Fillintheblanks
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
Trueorfalse
9 F
0 T
F
2 F
3 T
4 F
5 T
6 T
7 T
8 T
2
Multiplechoicequestions
9 B
20 A
2 A
22 D
23 B
24 C
25 C
26 D
27 D
28 D
29 A
30 C
3 A
32 D
33 C
34 C
35 B
36 D
37 B
38 C
39 A
40 B
4 D
3
42 A
43 B
44 D
45 A
46 C
47 D
48 C
49 C
50 B
5 D
52 A
53 B
54 B
55 D
56 C
57 D
58 C
59 C
60 C
6 D
62 A
63 C
64 B
65 B
66 C
4
67 A
68 B
69 B
70 D
7 B
72 D
73 C
74 B
75 A
76 D
Unit 30 Isomerism
Fillintheblanks
structural
2 stereoisomers
3 Enantiomers
4 chiral
5 opposite; optically active
Trueorfalse
6 T
7 F
8 F
9 T
0 T
F
2 T
5
3 F
4 T
5 F
Multiplechoicequestions
6 B
7 D
8 B
9 B
20 C
2 D
22 A
23 D
28 C
25 B
26 C
27 B
28 C
29 C
30 D
3 B
32 A
33 B
34 B
35 B
6
36 B
37 B
38 A
39 D
40 B
4 C
42 C
43 B
44 A
45 A
46 D
47 B
48 B
49 C
50 D
5 B
52 A
53 B
54 A
55 B
56 B
57 C
58 C
59 B
7
60 B
6 A
62 A
63 C
64 B
65 C
66 D
67 C
68 B
69 D
70 A
7 D
72 D
73 C
74 C
Unit 31 Typical reactions of selected functional groups
Fillintheblanks
addition / hydrogenation
2 substitution / hydrolysis
3 substitution
4 dehydration / elimination
5 oxidation
6 reduction
7 esterification / condensation
8 hydrolysis
8
Trueorfalse
9 T
0 F
F
2 F
3 T
4 T
5 T
Multiplechoicequestions
6 C
7 C
8 B
9 D
20 D
2 C
22 C
23 A
24 C
25 B
26 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.
27 B
28 C
29 C
30 D
9
3 A
32 A
33 D
34 C Option A The acidified potassium dichromate solution acts as an oxidizing agent.
Option B Propanoic acid is the final product.
Option C Propan--ol is first oxidized to propanal and then to propanoic acid.
Option D The reaction mixture changes from orange to green as the dichromate ions are reduced to
chromium(III) ions.
35 C
36 B
37 C
38 B
39 C
40 A
4 B
42 C
43 A
44 D
45 A
46 D
47 C
48 A
49 C
50 C
5 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 ethanol to propanoic acid rather than to propanal.
0
52 D
53 B
54 D Ethanol in the wine is oxidized to ethanoic acid. The acid makes the wine tastes sour.
55 B
56 C
57 C
58 D
59 B
60 C
6 A
62 C
63 D
64 A
65 B
66 A An ester is formed when a carboxylic acid reacts with an alkanol. The reaction is known as
esterification.
67 D The rate of esterification is slow. Hence concentrated sulphuric acid is used as a catalyst to speed up the
reaction.
68 B C O H +
O
CH
3
C O CH
3
O
CH
3
O CH
3
H + H
2
O
+ + carboxylic acid alcohol ester water
69 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
7 C
72 D
73 C

74 A
75 B
76 C
77 B
78 A
79 A
80 C
8 C
82 B
83 B
84 D
85 B
86 A
87 A
88 D
89 C CompoundXisanalcoholanditundergoesoxidationinthereaction.Thereactionmixturechangesfrom
orange to green as the dichromate ions are reduced to chromium(III) ions.
90 A
9 D
92 A The compound is ethyl ethanoate.
(3) It is produced from ethanol and ethanoic acid.
93 B
94 D
95 A
96 D
2
97 A
98 B
99 D
00A
0B
02C
03B
04C
05C
06C The reaction between ethanoic acid and ethanol is esterification.
07D The rate of esterification is slow. A catalyst such as concentrated sulphuric acid is used to speed up the
reaction.
08B
09A
0D
Unit 32 Synthesis of carbon compounds
Fillintheblanks
a) i) Br
2
(in organic solvent) ()
ii) Br
2
(aq) ()
ii) H
2
/ Ni catalyst ()
iii) HBr(g) ()
iv) MnO
4

/ OH

()
b) i) conc. H
2
SO
4
or conc. H
3
PO
4
or Al
2
O
3
, heat ()
ii) reflux with conc. HCl, ZnCl
2
catalyst; or mix with PCl
5
; or reflux with SOCl
2
()
iii) reflux with NaBr + conc. H
2
SO
4
; or reflux with red P + Br
2
()
iv) reflux with Nal + conc. H
3
PO
4
; or reflux with red P + I
2
()
v) heat with K
2
Cr
2
O
7
/ H
3
O
+
, distil off the product ()
vi) CH
3
COOH, conc. H
2
SO
4
, heat ()
3
c) i) reflux with K
2
Cr
2
O
7
/ H
3
O
+
()
ii) LiAlH
4
/ ethoxyethane; 2 H
3
O
+
()
iii) concentrated H
2
SO
4
, heat ()
iv) reflux with NaOH(aq) ()
v) NH
3
(aq); 2 heat ()
vi) HCl(aq), heat ()
vii)reflux with NaOH(aq) ()
Trueorfalse
2 F
3 T
4 T
5 F
6 F
Multiplechoicequestions
7 A
8 A
9 D
0 A
C
2 D
3 C
4 D
5 C
6 D
7 C
8 C
9 C
4
20 C
2 D
22 B
23 D
24 B
25 B
26 D
27 D
28 B
29 A
30 D
3 C
32 D
33 C
34 C
35 A
36 A
37 C
38 C
39 B
40 B
4 A
42 D
43 C
44 A
5
45 A
46 D
47 B
48 B
49 A
50 B
5 C
52 A
53 C
54 C
Unit 33 Important organic substances
Fillintheblanks
fats; oils; saponification
2 calcium; magnesium
3 scum
4 non-biodegradable
5 hydrogen
6 condensation
7 monosaccharides
8 glucose; frustose
9 triglyceride
0 amino acid
Trueorfalse
T
2 F
6
3 F
4 F
5 T
6 T
7 F
8 T
9 T
20 F
Multiplechoicequestions
2 B
22 C
23 D The hydrocarbon tail is soluble in grease and oil, i.e. hydrophobic. The ionic head is soluble in water,
i.e. hydrophilic.
24 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 Concentrated sodium chloride solution lowers the solubility of soap in water. The soap separates from
the solution and floats on the surface.
26 D
27 B
28 A Detergents I and IV are soaps. They would form scum with hard water.
29 C Detergent III is non-biodegradable.
30 B Detergents II and III are soapless detergents.
3 B
32 C
33 D The ionic head of a soap particle is usually a C O

O
group.
7
34 A Option A Sea water is hard water and contains a relatively high concentration of magnesium salts.
Major elements found in sea water
Element Content (parts per million, ppm)
Chlorine 9 500
Sodium 0 770
Magnesium 290
Sulphur 905
A soap solution forms scum with sea water. A proper lather cannot form until the soap has
reacted with all the magnesium salts in the sea water.
Option B The tap water in Hong Kong is soft water.
35 A
36 D The calcium carbonate deposit can be removed by an acid. Vinegar contains ethanoic acid.
CaCO
3
(s) + 2H
+
(aq) Ca
2+
(aq) + CO
2
(g) + H
2
O(l)
37 B
38 D
39 B
40 D
4 B
42 A
43 A
44 A
45 D
46 A
47 D
48 D
49 B
50 A
8
5 B () Hard water contains a great amount of dissolved calcium and magnesium salts.
(2) Sea water contains a relative high concentration of magnesium salts. Therefore sea water is hard
water.
(3) The tap water in Hong Kong is soft water.
52 D () The ionic head of a soapless detergent particle is usually a sulphonate SO
2
O

or sulphate
OSO
2
O

group.
53 B
54 A
55 A () 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
57 A
58 C (2) Nylon is a condensation polymer.
59 B
60 B () Poly(ethylene terephthalate) is common polyester. It is formed by the condensation of a diol and a
dioic acid.
(2) Poly(ethylene terephthalate) is a thermoplastic. There is no covalent bond between polymer chains.
6 D
62 D
63 A
64 C
65 B
66 D
67 B
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.
9
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.
7 D Detergents with branched-chain hydrocarbons are non-biodegradable. They cause more harm to the
environment when compared to those with straight-chain hydrocarbons.
72 A
73 B Soapless detergents do not form scum with either soft water or hard water.
74 D
75 C Nylon softens upon heating.
76 D
77 C
Part B Topic-based exercise
Multiplechoicequestions
C
2 D
3 C
4 B
5 A
6 C
7 A
8 A
9 A
0 A
B
2 A
20
3 B
4 D
5 D
6 C
7 A
8 B
9 B
20 C
2 C
22 B
23 C
24 B
25 C
26 C
27 D
28 C
29 B
30 D
3 C
32 C
33 D
34 D
35 C
36 C
2
37 D
38 B
39 D
40 D
4 C
42 C
43 C
44 B
45 A
46 C
47 B
48 A
49 B
50 D
5 B
52 A
53 C
54 C
55 D
56 A
57 C
58 B
59 C
60 B
22
6 D
62 A
63 A
64 D
65 D
66 A
67 A
68 C
69 D
70 B
7 C
72 D
73 A
74 C
75 A
76 C
77 D
78 B
79 D
80 A
8 B
82 B
83 D
84 A
23
85 A
86 B
87 C
88 A
Shortquestions
89 a) 4-methylpent-2-ene ()
b) 3-bromobut--ene ()
c) 2-chloro-2-methylhexane ()
d) pentan-2-ol ()
e) 2-ethylbutan--ol ()
f) hex-3-enal ()
g) 3-oxobutanoic acid ()
h) 4-methylpentan-2-one ()
i) 2-methylpropyl methanoate ()
j) 2-aminopropanoic acid ()
90 a)
() CH
3
CHCH
2
CHCH
3
CH
3
CH
3
b) CH
3
CH
2
CH
3


()
c)
C
O
CH
3

()
d)
CH
3
CH
2
CH
CH
3
CH
2
CH
3
O C
O

()
e) CH
2
=CHCONH
2
()
24
9 a) functional group isomers ()
b) chain isomers ()
c) position isomers ()
d) position isomers ()
e) functional group isomers ()
f) functional group isomers ()
92 a) no ()
b) yes ()
c) no ()
d) no ()
e) yes ()
f) yes ()
93 a)

C
Cl
C
*
H H
C
H
H H
C
H
C H
H
H
H
H

2-chloropentane

() ()
b)

OH
C
*
H H
C
H
H H
C
H
C H H
H

butan-2-ol

() ()
c)

C
H
C
CH
3
H
C
*
H
H H
C C H
H
H
H

3-methylpent--ene

() ()
e)

C COOH
CH
3
C
*
H
H H
C
H
H
H
2-methylbutanoic acid

() ()
f)

H CHO
Br
C
*
H
H H
C

2-bromopropanal

() ()
94 a) propane ()
b) ethanoic acid ()
25
c) ethyl ethanoate ()
d) butanamine ()
e) cyclohexene ()
f) butanal ()
95 a) and b)
Test Observation(s)
Type of reaction
involved
ShakeafewdropsofXwith
aqueous bromine.
The aqueous bromine changes from yellow-
brown to colourless quickly. ()
addition ()
Addphosphoruspentachloride
toX.Testanygasevolvedwith
moist blue litmus paper.
Steamy fumes are observed. ()
The moist blue litmus paper turns red. ()
substitution ()
Add aci di fi ed potassi um
dichromate solution to X
and heat the mixture.
The acidified potassium dichromate solution
changes from orange to green. ()
oxidation ()
96 a) Any one of the following:
Add solid sodium hydrogencarbonate (or solution). ()
X gives a gas that turns limewater milky. ()
Use moist blue litmus paper / pH paper for testing. ()
X turns moist blue litmus paper / turns pH paper orange (or red). ()
b) Any one of the following:
Add aqueous bromine. ()
Y turns aqueous bromine from yellow-brown to colourless quickly. ()
Add cold acidified dilute potassium permanganate solution. ()
Y turns the permanganate solution from purple to colourless quickly. ()
Heat with acidified potassium dichromate solution. ()
Y turns the dichromate solution from orange to green. ()
26
97 a) Cl
2
/ ultraviolet; light ()
b)
CH
3
()
c) red P + I
2
; reflux ()
d) conc. H
2
SO
4
heat ()
e)
COOH
()
f) CH
3
CH(OH)CH
2
CH
3
()
g) NH
3
; 2 heat ()
h) LiAlH
4
/ ethoxyethane; 2 H
3
O
+
()
i) NaOH(aq); heat ()
j)
OH
COOH
()
98 a) CH
3
CH(OH)CH
2
OH ()
b)
C H
CH
2
CH
3
H
C
H
3
CH
2
C
Br
H
3
C
()
c)
C
CH
2
CH
3
C CH
3
Br
H
D
H
()
d)
O

()
e)
Cl
()
f) CH
3
CH
2
CH
2
I ()
g)
CHCH
2
CH
3
C
CH
3
CH
3
()
27
h) OH
CH
3
()
i)
NH
2
(1)
(1)
CH
3
CH
2
O
+ CH
3
COO

Na
+
99 a) i)

H
H
C
C
C OH
O
HO
C
H
H
C
OH
H
CH
2
OH
OH
()
ii) Carbonyl group ()
Hydroxyl group ()
b) i) Carboxyl group ()
ii)
C N C OH
H
CH
3
HO
H
H
C
CH
3
O
C
O
()

C O C OH
H
CH
3
H
2
N
H
C
CH
3
O
C
O
()
iii) Any one of the following:
Peptide link / amide functional group ()
Ester functional group ()
Structuredquestions
00a)

H
CH
3
CH
2
C CH
2
(1)
H
CH
3
H
CH
3
C C
(1)
H
CH
3
CH
3
H
C C
(1)
CH
3
CH
3
C CH
2
(1)
28
b) i)
H
CH
3
H
CH
3
C C
H
CH
3
CH
3
H
C C and are cis-trans isomers.
(1)
ii) In order for the intermolecular forces to work well, the molecules must be able to pack together
efficiently in the solid. ()
Molecule of the trans isomer has a more regular and symmetrical structure than molecule of 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.
0 a) 2-hydroxybenzaldehyde ()
b) Position isomerism ()
c) X can form intramolecular hydrogen bonds. ()
Y forms more intermolecular hydrogen bonds than X does. ()
Thus the melting point of Y is much higher than that of X.
02a) Any one of the following:
Warm each compound with acidified potassium dichromate solution. ()
A turns the dichromate solution from orange to green. ()
There is no observable change for B. ()
Warm each compound with acidified potassium permanganate solution. ()
A turns the purple permanganate solution colourless. ()
There is no observable change for B. ()
b) Put about 2 cm
3
of ethanol and cm
3
of silver nitrate solution in each of two test tubes. ()
Place the test tube in a water bath at 60 C. ()
Add several drops of C and D separately to each test tube.
A yellow precipitate forms rapidly in the test tube containing D. ()
A white precipitate forms slowly in the test tube containing C. ()
c) Warm each compound with acidified potassium dichromate solution. ()
F turns the dichromate solution from orange to green. ()
There is no observable change for E. ()
29
d) Add aqueous bromine to each compound separately. ()
G decolorizes aqueous bromine quickly. ()
There is no observable change for H. ()
03a) i) hydroxyl group ()
ii) carbonyl group ()
iii) carboxyl group ()
b) LiAlH
4
/ ethoxyethane ()
2 H
3
O
+
()
c) Excess concentrated sulphuric acid ()
80 C ()
d) V ()
K
2
Cr
2
O
7
/ H
3
O
+
()
e) Any one of the following:
Warm each compound with acidified potassium dichromate solution. ()
U turns the dichromate solution from orange to green. ()
There is no observable change for Y. ()
Mix each compound with phosphorus pentachloride. ()
U gives steamy fumes of hydrogen chloride. ()
There is no observable change for Y. ()
f) Heat V and Z under reflux in the presence of concentrated sulphuric acid. ()
CHCH
2
CH
3
O
CH
3
CH
3
CH
2
CH
2
C
O
()
g) V ()
*
CH
2
CH(OH)CH
2
CH
3
()
30
04a) i) Condenser ()
ii) Compound X is flammable. ()
iii) To ensure even boiling. ()
iv) Propanoic acid ()
[O]
v) CH
3
CH
2
CH
2
OH CH
3
CH
2
COOH ()
vi) As an oxidizing agent ()
vii)
thermometer
reaction mixture
anti-bumping
granules
water in
water out
gentle heat
condenser
aqueous solution
of propanoic acid
( mark for a correct set-up; mark for correct labels; 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 ()
ii) As a catalyst ()
iii) Heating under reflux can reduce the loss of volatile reactants / products by evaporation. ()
05a) i) substitution ()
ii) dehydration / elimination ()
iii) addition ()
b) i) Cl
2
()
ultraviolet light / sunlight ()
ii) sodium hydroxide solution ()
reflux / heat ()
iii) excess concentrated sulphuric acid ()
80 C ()
c) i) Structural isomers are compounds with the same molecular formula, ()
but differ in the order in which atoms are linked. ()
3
ii)
Alcohol Classification
CH
3
CH
2
CH
2
CH
2
OH
primary
(0.5)
CH
3
CH
2
CHCH
3
OH
secondary
(0.5)
CH
3
CHCH
2
OH
CH
3
()
primary
(0.5)
CH
3
COH
CH
3
CH
3
()
tertiary
(0.5)
d) Any one of the following:
HCl(g) () in the presence of ZnCl
2
catalyst ()
reflux with concentrated hydrochloric acid () using ZnCl
2
as catalyst ()
reflux () with sulphur dichloride oxide ()
mix () with phosphorus pentachloride ()
e) i) Dehydration ()
ii) CH
3
CH=CHCH
3
()
06a) Carbon-carbon double bond ()
Hydroxyl group ()
b)
C CH
2
CH
2
OH
CH
3
H
C
H
H
H 3-methylbutan--ol
() ()

C CH
2
CH
2
OH
CH
3
Br
C
H
Br
H
2,3-dibromo-3-methylbutan--ol

() ()
c) i) 3-methylbut-3-enoic acid ()
ii) Heat under reflux ()
with acidified potassium dichromate solution ()
32
iii)

H
H
CH
3
CH
2
CHO
C C

or 3-methylbut-3-enal ()
d)
H
H
CH
3
CH
2
CH
2
OH
C C +
H
CH
3
Br
C H C CH
2
CH
2
Br
H
2HBr (1) + H
2
O (1)
07a)
C Br
H
H
C
H
H
H

()
b) i) Heat under reflux ()
with acidified potassium dichromate solution ()
ii) React with aqueous ammonia to form an ammonium salt. ()
Evaporate the water and subsequently heat the dry salt. ()
c) i) Substitution ()
ii) Oxidation ()
iii) Reduction ()
d) CH
3
COOH > CH
3
CH
2
OH > CH
3
CH
2
NH
2
()
The boiling point of a compound depends on its molecular attractions. ()
All the compounds can form hydrogen bonds.
Molecules of CH
3
COOH can form more extensive hydrogen bonds than those of CH
3
CH
2
OH. ()
Thus the boiling point of CH
3
COOH is higher than that of CH
3
CH
2
OH.
Since oxygen is more electronegative than nitrogen, the OH bond in CH
3
CH
2
OH is more polar than the
NH bond in CH
3
CH
2
NH
2
.
As a result, stronger hydrogen bonds exist between molecules of CH
3
CH
2
OH. ()
Thus the boiling point of CH
3
CH
2
OH is higher than that of CH
3
CH
2
NH
2
.
08a) Carbon-carbon double bond ()
Carbonyl group ()
b) i) Stereoisomers have their atoms linked in the same way, ()
but they differ in the spatial arrangement of their atoms. ()
ii) Geometrical isomerism ()
33
iii) Due to the restricted rotation about a carbon-carbon double bond. ()
iv) Identical methyl groups attach to one of the carbon atoms of the C=C bond. ()
c) i) CHCH
2
CH
2
C
CH
3
CHCH
2
OH (H
3
C)
2
C
()
ii) Primary alcohol ()
There is one alkyl group attached to the carbon bearing the OH group. ()
iii) LiAlH
4
/ ethoxyethane
2 H
3
O
+
()
iv) ()

CHCH
2
CH
2
C
CH
3
CHCH
2
(H
3
C)
2
C O CH
3
C
O
()
(2) Esterification
09a)

CH
3
CHCH
2
Br
CH
3
()
b)

C
CH
3
CH
2
CH
3 ()
methylpropene ()
c) i)

CH
3
CBrCH
3
CH
3
()
2-bromo-2-methylpropane ()
ii) Structural isomers are compounds with the same molecular formula, ()
but differ in the order in which atoms are linked. ()
iii) CH
3
CH
2
CH
2
CH
2
Br ()
CH
3
CH
2
CHBrCH
3
()
0a)
C
H
C H
H
H
Br
C
H
Br ()
34
b) X, Y and Z are formed from the dehydration of alcohol W.
Thus they are alkenes. ()
X and Y react with bromine to give ,2-dibromo--phenylpropane, i.e.
C
H
C H
H
H
Br
C
H
Br
.
It can be deduced that the structures of X and Y are as follows:
H H
(1)
CH
3
C C
H CH
3
(1)
H
C C
Z reacts with bromine to give 2,3-dibromo--phenylpropane, i.e. C
H
C H
Br
H
Br
C
H
H
.
It can be deduced that the structure of Z is as follows:
C
H
C H
H
C
H
H ()
W undergoes dehydration to give X, Y and Z. It can be deduced that the structure of W is as follows:
C
H
C H
H
H
OH
C
H
H ()
c) X and Y exhibit geometrical isomerism. ()
X, Y and Z exhibit structural / position isomerism. ()
d) i) The purple permanganate solution becomes colourless quickly. ()
ii)
C
H
C H
H
H
OH
C
H
OH ()
35
a) i) Suppose we have 00 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
in the
compound
40.0 g 6.65 g 53.3 g
Number of
moles of
atoms that
combine
40.0 g
2.0 g mol

= 3.33 mol
6.65 g
.0 g mol

= 6.65 mol
53.3 g
6.0 g mol

= 3.33 mol
()
Simplest
ratio of
atoms
3.33 mol
3.33 mol
=

6.65 mol
3.33 mol
= 2
3.33 mol
3.33 mol
=
()
the empirical formula of X is CH
2
O.
ii) Let (CH
2
O)
n
be the molecular formula of X.
Relative molecular mass of X = n(2.0 + 2 x .0 + 6.0)
= 30n
i.e. 30n = 90.0
n = 3
the molecular formula of X is C
3
H
6
O
3
. ()
b) Effervescence occurs when X is mixed with sodium hydrogencarbonate solution. Thus it should be a
carboxylic acid and contain a COOH group. ()
X undergoes esterification with ethanoic acid. Thus it should contain a OH group. ()
X is chiral. Thus it should contain at least one chiral carbon. ()
Structure of X:

2-hydroxypropanoic acid
OH
C
O
C OH H
H
chiral carbon
C
H
H
()
()
c)
O
C
O
C OH H C
H
H
()
36
d)
O
C
C
O
O
C O
C
H H
CH
3
CH
3
()
Ester functional group ()
2Since W can be hydrolyzed to give an acid X and a neutral compound Y, so W should be an ester. ()
Relative molecular mass of W = 0 x 2.0 + 2 x .0 + 2 x 6.0 = 64.0
Relative molecular mass of Y = 64.0 + 8.0 22.0 = 60.0 ()
Let the molecular formula of Y be C
n
H
2n+
OH.
i.e. 2n + 2n+ + 6.0 + .0 = 60.0
n = 3
the molecular formula of Y is C
3
H
7
OH () and that of X is C
7
H
6
O
2
or C
6
H
5
COOH. ()
The structure of X is
COOH
. ()
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. ()
Z is propanone, CH
3
COCH
3
. ()
Y is a secondary alcohol, CH
3
CHCH
3
OH
. ()
W is
COOCH(CH
3
)
2
. ()
3a)
CH
3
CH
2
CH
2
CH
2
Br CH
3
CH
2
CH
2
CH
2
OH
NaOH(aq)
reux
(1) (1)
CH
3
CH
2
CH
2
COOH
K
2
Cr
2
O
7
/ H
3
O
+
reux
(1)
37
b)
conc. H
2
SO
4
heat
(1) (1)
CH
2
CH
2
OH CH CH
2
HBr(g)
(1) (1)
NaOH(aq)
reux
(1) (1)
CHBrCH
3
CH(OH)CH
3
K
2
Cr
2
O
7
/ H
3
O
+
(1)
reux
CCH
3
O
c)
CH
3
CHCH
2
OH
cold alkaline
dilute KMnO
4
(1)
OH
CH
3
CHCH
3
CH
3
CH
conc. H
2
SO
4
heat
(1) (1)
CH
2
OH
d)
NaOH(aq)
reux
(1)
CH
2
CH
2
Br
K
2
Cr
2
O
7
/ H
3
O
+
reux
(1) (1)
CH
2
CH
2
OH
CH
3
OH / conc. H
2
SO
4
heat
(1)
CH
2
COOCH
3
(1)
CH
2
COOH
e)
CH
2
CONH
2
CH
2
COOH
H
3
O
+
(1) (1)
CH
2
CH
2
OH
1 LiAlH
4
/ ethoxyethane
2 H
3
O
+
heat
(1)
f)
NaOH(aq)
reux
(1)
conc. H
2
SO
4
or conc. H
3
PO
4
heat
(1) (1)
Cl OH
(1)
Br
2
(in organic solvent)
(1)
Br
Br
38
4a) 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. ()
Modification add a receiver adaptor between the condenser and the round-bottomed flask. ()
b) i) Use a teat pipette to remove the bottom layer. / Use a separating funnel and run off the bottom
layer. ()
ii) To dry the organic layer. ()
iii) Any one of the following:
Add aqueous bromine to the distillate. ()
The yellow-brown aqueous bromine changes to colourless quickly. ()
Add cold acidified dilute potassium permanganate solution to the distillate. ()
The purple permanganate solution changes to colourless quickly. ()
iv) Add phosphorus pentachloride to the distillate. ()
Steamy fumes would be observed. ()
5a) The process is exothermic. ()
b) i) To remove the excess dilute sulphuric acid. ()
ii)
aqueous layer
1-bromopropane layer
( mark for correct drawing of separating funnel with tap; mark for showing -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. ()
c) To dry the product. ()
d) Use an electric heating mantle / a water bath / an oil bath for heating ()
because propan--ol / -bromopropane is flammable. ()
39
e) i)
anti-bumping
granules
water out
water in
heat
condenser
glass beads
fractionating
column
still head
thermometer
organic
layer
receiver
adaptor
distillate
( mark for correct set-up; mark for correct labels; mark for correct drawing of fractionating
column; 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 ()
f) i) Number of moles of propan--ol =
9.2 g
60.0 g mol

= 0.52 mol
According to the equation, mole of propan--ol gives mole of -bromopropane.
Theoretical yield of -bromopropane = 0.52 mol x 22.9 g mol

= 8.7 g ()
Percentage yield of -bromopropane =
0.8 g
8.7 g
x 00%
= 57.8% ()
ii) Any one of the following:
The reaction is incomplete. ()
Some of the propan--ol dehydrate to form an alkene. ()
Some of the product stay in the aqueous layer. ()
6a) Methanol () and propanoic acid ()
b) As a catalyst ()
c) CH
3
OH(l) + CH
3
CH
2
COOH(l) CH
3
CH
2
COOCH
3
(l) + H
2
O(l) ()
d)
C O
O H
C
H
H
C C H
H
H
H
H ()
40
e) Methanol is flammable and it catches fire easily. ()
f) Any two of the following:
A pleasant smell could be detected. () / An insoluble layer formed on the sodium carbonate solution.
() / Effervescence occurred. ()
g) B ()
h) Any one of the following:
propyl methanoate
(1) (1)
(1) (1) (1) (1) C OCH
2
CH
2
CH
3
O
H ethyl ethanoate C OCH
2
CH
3
O
CH
3
methylethyl methanoate C OCH(CH
3
)
2
O
H
i)
(1) (1) butanoic acid
C
H
H
C
H
H
C OH
H
H
H
O
C
(1) methylpropanoic acid (1)
C
CH
3
H
C OH
H
H
H
O
C
7a)
water out
water in
reflux condenser
heat
mixture of ethyl
benzoate and
excess NaOH(aq)
anti-bumping
granules
( mark for correct set-up; 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. ()
c) To convert sodium benzoate into benzoic acid. ()
4
d) Dissolve the crude sample in minimum amount of hot water. ()
Filter the mixture while hot. ()
Allow the filtrate to cool and collect the crystals by filtration. ()
e) i) Number of moles of ethyl benzoate =
4.50 g
50.0 g mol

= 0.0300 mol
According to the equation, mole of ethyl benzoate gives mole of benzoic acid on hydrolysis.
Theoretical yield of benzoic acid = 0.0300 mol x 22.0 g mol

= 3.66 g ()
Percentage yield of benzoic acid =
2.29 g
3.66 g
x 00%
= 62.6% ()
ii) Hydrolysis is not complete. / Benzoic acid is slightly soluble in water. ()
8a) 3-methylbutyl ethanoate ()
b) (CH
3
)
2
CH(CH
2
)
2
OH ()
3-methylbutan--ol ()
c) Reagent Y is concentrated sulphuric acid. ()
Heat the reaction mixture under reflux. ()
d) Esterification
e) Any two of the following:
Isoamyl acetate ()
Acetic acid ()
Water ()
d) Shake the mixture with sodium hydrogencarbonate solution until no more gas is evolved. ()
Extract the isoamyl acetate from the organic layer using ethoxyethane. ()
Remove the ethoxyethane by simple distillation. ()
9a) i) Cause bleeding in the stomach lining ()
ii) Paracetamol ()
b) i) 2-hydroxybenzoic acid ()
ii) Heat with methanol ()
and a little concentrated sulphuric acid. ()
42
iii)
COO

Na
+
OH

()
c) Number of moles of salicylic acid used =
8.28 g
38.0 g mol

= 0.0600 mol ()
Number of moles of aspirin obtained =
7.20 g
38.0 g mol

= 0.0400 mol ()
Percentage conversion =
0.0400 mol
0.0600 mol
x 00%
= 66.7% ()

d) To show the presence of the COOH group, add sodium hydrogencarbonate solution to the
compound. ()
Evolution of colourless gas bubbles indicates the presence of the COOH group. ()
To show the presence of the ester group, heat the compound with dilute acid. ()
Smell of vinegar is noted. ()
e) i) Ca(OH)
2
()
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. ()
The large hydrophobic benzene ring also leads to low water solubility. ()
The calcium salt is ionic. Strong interactions exist between water and the ions. ()
20a) Saponification ()
b)
O C C
17
H
33
O
H
2
C
O C C
17
H
33
+ 3NaOH
O
HC
O C C
17
H
33
O
H
2
C
OH H
2
C
OH + 3C
17
H
33
COO

Na
+
HC
OH H
2
C
(2)
c) Label C ()
43
d) Any one of the following:
Wear safety glasses. ()
Wear protective gloves. ()
e) To lower the solubility of soap in water. ()
f) To prevent the soap from dissolving in the water. ()
g) Perfume () and colouring ()
h) Not suitable ()
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. ()
2a) Any two of the following:
Hydrocarbons obtained from petroleum ()
Concentrated sulphuric acid ()
Sodium hydroxide ()
b) i)
O S O

O
O
()
ii) CH
3
(CH
2
)
0
CH
2
()
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. ()
Uponshaking,oildropletsform.Eachdropissurroundedbydetergentparticleswiththehydrophilicparts
in the water. ()
The hydrophilic parts carry negative charges and prevent the oil droplets from coming together again.
Hence an emulsion is formed. ()
d) Detergent X can emulsify the crude oil into droplets and ()
the droplets can be carried out away by water currents. ()
e) i) Yes ()
ii) Duringthedecompositionofthedetergent,bacteriauseupoxygeninthewater.Thismakesthewater
smell badly due to oxygen depletion. ()
f) i) Calcium ion ()
Magnesium ion ()
ii) Detergent X can function well in hard water ()
because it does not form scum with hard water. ()
44
22a) i) Carboxyl group ()
ii) Hydroxyl group ()
b) Sodium hydroxide solution ()
c)
O CH
2
CH
2
O
O
C
O
C
()
d) Condensation polymerization ()
e) Permanent dipole-permanent dipole attractions between PET polymer chains are stronger ()
than the instantaneous dipole-induced dipole attractions between polythene polymer chains. ()
f) i) Hydrolysis ()
ii) HO CH
2
CH
2
OH ()

O

Na
+
O
C
O
C Na
+
O

()
23a i) The molecule of valine contains one carbon atom bonded to four different groups of atoms. ()
ii)
NJSSPS
(1)
(CH
3
)
2
HC
NH
2
COOH
C
H
(1)
CH(CH
3
)
2
H
2
N
HOOC
C
H
iii) () Rotation of plane of plane-polarized light ()
(2) Rotate the plane of plane-polarized light in opposite directions. ()
b)
CH N
O CH(CH
3
)
2
C CH COOH
CH
3
H
H
2
N
()

CH N
O CH
3
C CH COOH
CH(CH
3
)
2
H
H
2
N
()
45
c) CH
3
H
3
N
+
CHCOOH
(1)
CHCOO

CH
3
H
2
N
(1)
24a) Amine functional group (), carboxyl group (), amide functional group (), ester functional group ()
b)
O
C NH H
2
N CH
CH
2
CO
2
H
*
O
C OCH
3
CH
CH
2
*
(2)
c)
C OH
O
C
H
CH
2
COOH
H
2
N
()

CHCH
2
COOH
H
2
N
()
d) Silicon dioxide increases the bulk mass of the sweetener. ()
e) Phenylketonurics are unable to metabolize the phenylalanine produced from the hydrolysis of
aspartame. ()
A high level of phenylalanine in the brain is extremely harmful and sometimes fatal. ()
25a) Condensation polymerization ()
b)
N (CH
2
)
6
N H
H
H
H ()

O (CH
2
)
4
O
C C H H O
O ()
46
c)
(CH
2
)
4
O
C C
O
N (CH
2
)
6
N
H
H
()
d) Any one of the following:
Lighter in weight ()
Does not corrode easily ()
e) There are hydrogen bonds between the polymer chains of nylon. ()
Only weak instantaneous dipole-induced dipole attractions exist between the polymer chains of
polythene. ()
Hence nylon is stronger than polythene.
f) A hole would appear ()
because the acid hydrolyzes the amide linkages in nylon. ()
g) Method I:
The waste contains dichromate ions which is toxic. ()
Method II:
Concentrated nitric acid is a strong acid. Discharge of the waste into waterways leads to environmental
pollution. ()
26a) Any two of the following:
Burning fossil fuels produces a lot of air pollutants. ()
The resources of fossil fuels are limited. ()
Supplyandpriceofpetroleummaybecomeunstableintimesofpoliticalunstabilityinpetroleum-producing
countries. ()
Petroleum spills during drilling or transportation cause major damage to ecosystems both on land and at
sea. ()
b) Burning ethanol returns carbon dioxide ()
which has been recently removed from the atmosphere during the photosynthesis of plants. ()
c) More energy can be obtained. ()
d) Any two of the following:
Farmers use fossil-fuel-powered equipment to plant, maintain and harvest the corn. ()
47
Fossil-fuel-powered machines are required to process the corn into ethanol. ()
Ethanol is transported to collection points via fossil-fuel-powered transport. ()
e) Any one of the following:
This may lead to diversion of investment from food production, resulting in increased food prices. ()
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. ()
f) As a solvent ()
27Any three of the following properties:
Physical properties
Hydrogen bonds exist between ethanol molecules. ()
Thustheboilingpointofethanolishigherthanthoseofalkanes/haloalkanesofsimilarrelativemolecular
masses. ()
Due to the hydrogen bonding between ethanol molecules and water molecules, ()
ethanol is miscible with water in all proportions. ()
Chemical properties
Ethanol reacts with hydrogen halides to form haloethanes. ()
Bromoethanecanbepreparedbyheatingamixtureofethanol,sodiumbromideandconcentratedsulphuric
acidunderreflux.Concentratedsulphuricacidreactswithsodiumbromidetoproducehydrogenbromide.
Hydrogen bromide then reacts with ethanol to give bromoethane. ()
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. ()
Ethanol can be dehydrated to form ethene. ()
This is done by heating ethanol at 80 C with excess concentrated sulphuric acid / passing ethanol
vapour over aluminium oxide at 300 C. ()
Ethanol can be oxidized to ethanal, and then to ethanoic acid. ()
This is done by heating ethanol with acidified potassium dichromate solution under reflux. The reflux
condenserpreventsanylossofthereactionmixtureandfavourstheoxidationofethanoltoethanoicacid
rather than to ethanal. ()
Ethanol reacts with carboxylic acid in the presence of concentrated sulphuric acid to form an ester. ()
For example, heating ethanol with methanoic acid in the presence of concentrated sulphuric acid gives
the ester ethylmethanoate. ()
(3 marks for organization and presentation)
48
28Add water to the liquids. ()
Both butanoic acid and propanone can mix with water in all properties. ()
Add a piece of pH paper to the aqueous solutions. ()
Solution of butanoic acid is acidic while that of propanone is not. ()
Add aqueous bromine to the remaining two compounds. ()
Only cyclohexene can decolorize the aqueous bromine quickly. ()
OR
Add silver nitrate solution to the remaining two compounds. ()
Only -bromobutane gives a pale yellow precipitate slowly. ()
(3 marks for organization and presentation)
29Soaps are mainly made from the reaction between fats (or vegetable oil) and sodium hydroxide
solution. ()
Soapless detergents are made from hydrocarbons obtained from petroleum, concentrated sulphuric acid and
sodium hydroxide. ()
Both of them have good cleaning ability in soft water. ()
However, soaps form scum and lose cleaning ability in hard water while soapless detergents do not. ()
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. ()
Soapsandstraight-chainedsoaplessdetergentsarebiodegradable.Whentheyaredecomposedbybacteriain
rivers or sea, oxygen in water is used up. This leads to oxygen depletion and thus causes death of aquatic
lives. ()
Ingeneral,soapsandstraight-chainedsoaplessdetergentscausefewerpollutionproblemsthanbranch-chained
soapless detergents.
(3 marks for organization and presentation)