HKDSE Chemistry

Suggested Answer
of
Assignment for Part XI

(Structured Questions)

Chemistry of Carbon Compounds

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
1. a. hex-2-ene b. 3-methylpent-2-ene

c. 3-chlorobut-1-ene d. 3-bromo-2-chloropentane

e. iodocyclohexane f. 2-chlorobutane

g. 4-methylpentan-1-ol h. 4-hydroxybenzaldehyde

i. 2-chloropentanal j. 4-hydroxyhexan-3-one

k. phenylethanoic acid l. propanedioic acid

m. 2,6-diaminohexanoic acid n. propanamide

o. phenyl benzoate p. potassium phenylethanoate

q. 2-methylbutyl methanoate

2. a. b.

c. d.

e. f.

g. h.

i. j.

k. l.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
3. a. Compound X: does not exhibit stereoisomerism.

Compound Y: Cis-trans isomerism.

Compound Z: Enantiomerism.

b.

4 a. i. Geometrical isomerism

ii. A can form intramolecular hydrogen bonds.

B forms more intermolecular hydrogen bonds than A does.

Thus the melting point of B is much higher than that of A.

iii. B can form extensive intermolecular hydrogen bonds between its molecules.

These hydrogen bonds have to be broken before water can dissolve B.

A has a net dipole moment while B has no net dipole moment.

This favours the dissolving of A in water.

b. D
In addition to intermolecular attractions, the melting point of a compound depends
also on the degree of compactness of molecules in the solid state.

Van der Waals’ forces exist in both C and D and they are of comparable strength.

D is more symmetrical and thus can pack more compactly in the solid.

Thus the melting point of D is higher.

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
5. a. Cl2 . UV light / sunlight / heat

b. Aqueous bromine

c. Any one of the following:

‧ Reflux with conc. HCl + ZnCl2 catalyst

‧ Mix with PCl5

d. H2 Pt catalyst

e. f. g

6. a. b. c

d e f

CH3CH=CHCH3

g.
(CH3)2C=CHCH2CH3

7. a. b.

CH3CH(OH)CH3 or CH3CH2CH2OH

c. d.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
e. f.

g. h.

CH3(CH2)3CH=CH2

i.

8. a. Any one of the following:

‧ Warm each compound with acidified potassium dichromate solution.

turns the orange dichromate solution green.

There is no observable change for .

‧ Warm each compound with acidified potassium permanganate solution.

turns the purple permanganate solution colourless.

There is no observable change for .

b. Put about 2 cm3 of ethanol and 1 cm3 of silver nitrate solution in each of two test tubes.

Add the compounds to the test tubes separately.

Place the test tubes in a water bath at 60 oC.

Precipitate first appears in the test tube containing .

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
c. Mix each compound with sodium hydrogencarbonate solution separately.

CH3CH2COOH gives a gas that turns limewater milky.

There is no observable change for CH3COOCH3.

d. Any one of the following:

‧ Mix with phosphorus pentachloride.

Only gives steamy fumes.

‧ Warm with a carboxylic acid in the presence of concentrated sulphuric acid.

gives a product with a sweetish / pleasant smell.

Only

e. Mix each compound with aqueous bromine in the absence of light separately.

decolorizes the aqueous bromine.

There is no observable change for .

9. a.

b.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
c.

d.

e.

f.

10. a.

b. Dehydration

c. i. Aluminium oxide

ii. So that the reaction may proceed faster, otherwise it may be too slow.

iii. The black substance is carbon which arises due to the thermal decomposition
of organic substances.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
d. To prevent the sucking back of the cold water into the hot apparatus, otherwise the
hot tube may crack.

e. i. CH3CHBrCH3

ii

11. a. Reagent – H2

Condition – Pt as catalyst / heat

b. i. CH3CH2CHBrCH3
2-bromobutane

ii. Addition reaction

c. KMnO4 / OH–

e.

12. a. i.
Isomer Systematic name
CH3CH2CH2CH2OH butan-1-ol

methylpropan-2-ol

methylpropan-1-ol

butan-2-ol

ii. Structural isomerism / chain and position isomerism

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds

b. i. Methylpropan-2-ol

ii. Dehydrating agent — 20% sulphuric acid / aluminium oxide

c. i. Isomer — butan-2-ol

Structure of ketone — CH3CH2COCH3

ii. 1. The reaction mixture turns from orange to green.

2. 3CH3CH2CH(OH)CH3 + Cr2O72– + 8H+  3CH3CH2COCH3 + 2Cr3+ + 7H2O

d. Isomer — butan-1-ol or methylpropan-1-ol

Structure of aldehyde — CH3CH2CH2CHO (1) or

e. Any one of the following:

‧ Warm with acidified potassium dichromate solution.

An aldehyde turns the orange dichromate solution green.

There is no observable change for a ketone.

‧ Warm with acidified potassium permanganate solution.

An aldehyde turns the purple permanganate solution colourless.

There is no observable change for a ketone.

f. i. A chiral molecule is one that is not superposable on its mirror image /
has no plane of symmetry.

ii. Butan-2-ol

iii.

iv. They rotate the plane of polarization of a beam of plane-polarized light

in opposite directions but with equal angles.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
13. a. A hydroxyl group

carbonyl group

B carboxyl group

b.
Property Compounds
i CANNOT be oxidized by acidified B
potassium dichromate solution E
A
ii are chiral
D

c. i. CH3CH2CH2CH2OH

Butan-1-ol

ii.

ethyl methylpropanoate

d Any one of the following:

ethyl ethanoate propyl methanoate

methyl propanoate methyl ethyl methanoate

14. a. i. A – propyl methanoate

B – butanoic acid

ii. Functional group isomerism

iii. Add sodium hydrogencarbonate solution to each compound.

B gives a gas that turns limewater milky.

There is no observable change for A.

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
b. i. C – pentan-2-one D – pentanal

ii. Any one of the following:

‧ Warm each compound with acidified potassium dichromate solution.

D turns the orange dichromate solution green.

There is no observable change for C.

‧ Warm each compound with acidified potassium permanganate solution.

D turns the purple permanganate solution colourless.

There is no observable change for C.

iii

15. a. The orange sodium dichromate solution turns green.

b. i. CH3COCH2CH3
butanone

ii. Functional group isomerism

c. i.

methylpropanal

ii. Chain isomerism

d. Esters

e. i

ii. CH3CH2CH2COOCH2CH3
ethyl butanoate
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
16. a. i. Propan-2-ol

ii. Concentrated sulphuric acid

iii. To prevent the loss of reactants / products by evaporation.

iv.

b. In flavourings / perfumes

c. i. Hydrolysis

ii.

iii. To act as a catalyst. / To react with the acid formed during the reaction.

iv. 1 Air condenser

2. Serving as a fractionating column for separating propan-2-ol from the

products formed.

3 Propan-2-ol

17. a.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
b. i.

ii. Run off and discard the lower aqueous layer.

Then run off the upper layer (to flask) / pour out the upper layer.

c. i. To absorb water from the organic product.

ii. Tiny water droplets in cylcohexene cause the cloudiness.

d. 82oC to 85oC

e. i. Mass of cyclohexanol used= 12.5 cm3 x 0.96 g cm–3 = 12.0 g

12.0 g
ii. Number of mole of cyclohexanol used = = 0.120 mol
100.0 g mol-1
= number of mole of cyclohexene obtained

Theoretical mass of cyclohexene obtained

= 0.120 mol x 82.0 g mol–1= 9.84 g

5.80 g
Percentage yield of cyclohexene = x 100% = 58.9%
9.84 g

iii. Any one of the following:

‧ The reaction is incomplete.

‧ Side reactions occur.

‧ Some of the product stays in the aqueous layer.

f. Any one of the following:

‧ Add aqueous bromine to the sample.

The yellow-brown bromine changes to colourless quickly.

‧ Add cold acidified dilute potassium permanganate solution to the sample.

The purple permanganate solution changes to colourless quickly.

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
18. a.

(1 mark for correct separating funnel with tap; 1 mark for showing the
2-methylbutan-2-ol layer on top; award 0 mark if the funnel is not workable)

b. i. To neutralize the excess hydrochloric acid.

ii. To prevent any pressure from building up due to the formation of

carbon dioxide gas.

c. i. To dry the organic product / to absorb the water from the organic product.

ii. The liquid product becomes clear after the drying process.

d.

e. Mass of 2-methylbutan-2-ol used = 6.00 cm3 x 0.805 g cm–3 = 4.83 g

4.83
Number of moles of 2-methylbutan-2-ol used = 80.0 g mol-1 = 0.0549 mol

= number of mole of 2-chloro-2-methylbutane obtained

Theoretical mass of 2-chloro-2-methylbutane obtained

= 0.0549 mol x 106.5 g mol–1 = 5.85 g

Actual mass of 2-chloro-2-methylbutane obtained

= 5.85 g x 65.0% = 3.80 g

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
19. a. CH3COOH(l) + CH3CH2OH(l) CH3COOCH2CH3(l) + H2O(l)

b. Ethyl ethanoate

c. As a catalyst

d.

(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)

e. To prevent any loss of volatile substances by evaporation.

f. Step 1: Transfer the distillate to a separating funnel. Shake with sodium carbonate
solution.

Step 2: Allow the aqueous and organic layers in the separating funnel to settle.
Run off the lower aqueous layer. Then run off the upper layer / pour out the
upper layer.

Step 3: Add calcium chloride solution to the organic layer and shake in a separating
funnel. Separate and discard the lower layer.

Step 4: Transfer the upper layer into a conical flask.

Add anhydrous calcium chloride.

Step 5: Filter or decant the liquid and re-distil. Collect the distillate with a boiling
range of 76 – 78 oC.

5.00g
20. a. Theoretical yield of benzoic acid = = 7.69 g
65.5%

7.69g
Number of moles of benzoic acid = = 0.0630 mol
122.0gmol1
= number of mole of benzamide

Mass of benzamide used = 0.0630 mol x 121.0 g mol–1 = 7.62 g

b. Measuring cylinder

Great accuracy is not required as sodium hydroxide solution is in excess.

c. Remove a little sample on a glass rod.

Test with some suitable indicator paper until the sample is acidic.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds

d. Dissolve in the minimum amount of hot water.

Filter while hot to remove insoluble impurities.

Cool the filtrate.

Filter while cold to leave soluble impurities in the solution.

e. i. Concentrated sulphuric acid

ii. Cyclohexanol /

iii. 1. Acidified potassium dichromate solution / acidified potassium

permanganate solution

2. Cyclohexanone /

21. A gives only two monochlorinated products, thus A should have three carbon atoms
per molecule.

B and C are haloalkanes which can be hydrolyzed to alcohols.

B gives an acid upon oxidation. Hence B is probably a primary alcohol.

C gives a ketone upon oxidation. Hence C is probably a secondary alcohol.

A – CH3CH2CH3 B – CH3CH2CH2Cl C – CH3CHClCH3

D – CH3CH2COOH E – CH3COCH3

22. a. i.

Z should be a secondary alcohol as it is formed by the reduction of a ketone.

Z does not have any carbon bonded to four different atoms or groups of atoms.

The carbon bearing the –OH group must have two identical groups bonded to it.

ii. Pentan-3-ol
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds

b. As Y can be hydrogenated to give Z, hence Y should be an alcohol containing

a C=C bond. X should have a C=C bond also.

Y has a chiral carbon, i.e. Y has a carbon bonded to four different atoms or groups
of atoms. X does not have geometrical isomers. Hence the C=C bond probably
appears at one end of the carbon chain.

23. a. Carboxyl group

b. 2-hydroxybenzoic acid

c. i.

ii

d. i. Van der Waals’ forces.Hydrogen bonds

ii. The –COOH group. It can form hydrogen bonds with water.

iii. 1.

2. Sodium salt is less acidic and more soluble.

24. a i.

ii. A chiral molecule is one that is not superimposable on its mirror image /
has no plane of symmetry.

b. They rotate the plane of plane-polarized light in opposite directions but

equal angles.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
c. i. Sodium hydroxide solution

ii

iii. Cr2O72–(aq) + 14H+(aq) + 6e–  2Cr3+(aq) + 7H2O(l)

d. i. 3-methylbutan-1-amine

ii.

iii Amide functional group.

25. a. Vegetable oil / animal fat and Sodium hydroxide

b. Hydrocarbons obtained from petroleum and concentrated sulphuric acid

c In the structure of detergent X, the hydrocarbon chain CH3(CH2)11- is hydrophobic

while the –COO– part is hydrophilic.

When mixed with a mixture of water and paraffin oil, the hydrocarbon chain
CH3(CH2)11- dissolves in the oil while the –COO– part dissolves in water.

Because of the repulsion between the –COO- on the surface of the large oil droplets,
upon shaking, small oil droplets form. Each small droplet is surrounded by detergent
particles with the anionic parts in the water.

Repulsion of the anionic parts prevents the oil droplets from coming together again.
Thus an emulsion forms.

d. i. Calcium ions and magnesium ions

ii. Detergent Y
When detergent X is added to hard water, it reacts with calcium ions and
magnesium ions to form insoluble products, i.e. scum.
A lot of soap is needed to get a lather.
Detergent Y does not form insoluble products with calcium ions and magnesium
ions, i.e. no scum forms.

iii. Washing soda reacts with calcium ions and magnesium ions in hard water to
form insoluble carbonates, thus removing the hardness of water.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
26. a. i. Sodium hydroxide

ii. Saponification / alkaline hydrolysis

Heat the animal fat with concentrated sodium hydroxide solution.

Add concentrated sodium chloride solution to the mixture to lower the

solubility of soap in water.

Filter the soap from the resulting mixture.

iii.

b. 9 x 12.0 + 14 x 1.0 + 6 x 16.0 + 42n = 806

n = 14

c. Not suitable

Sea water contains a lot of metal ions, such as calcium ions and magnesium ions.

Detergent X will react with these metal ions to form scum.

d. Detergent X is biodegradable.

During the decomposition of the detergent X by bacteria in water, oxygen in water

is used up.

This leads to oxygen depletion and causes the death of aquatic lives.

e. i. Ester functional group and carbon-carbon double bond

ii. Most carbon-carbon double bonds will be converted to single bonds.

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
27. a.

b. Saponification / alkaline hydrolysis

c NaOH(aq) + HCl(aq)  NaCl(aq) + H2O(l)

? mol dm–3 0.650 mol dm–3

100.0 cm3 15.4 cm3

10.0 cm3 (used)

45.4
Number of moles of HCl = 0.650 mol dm–3 x dm3 = 0.0100 mol
1000

Number of moles of NaOH in 10.0 cm3 solution = 0.0100 mol

Number of moles of NaOH remaining in the resulting solution

= 10 x 0.0100 mol = 0.100 mol

Number of moles of NaOH originally used

100.0
= 2.50 mol dm–3  dm3 = 0.250 mol
1000

Number of moles of NaOH reacted with fat = (0.250 – 0.100) mol = 0.150 mol

0.150
Number of moles of fat reacted = mol = 0.0500 mol
3

Molar mass of fat = [9 x 12.0 + 14 x 1.0 + 6 x 16.0 + 3n(12.0 + 2 x 1.0)]

= (218.0 + 42n) g

Mass of fat reacted = 0.0500 mol x (218.0 + 42n) g mol–1 = 44.5 g

∴ n = 16

d. To lower the solubility of soap in water.

e. i.

ii. CH3(CH2)14CH2—
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
28. a. The methyl orange solution turns yellow.

b. Ammonia is irritating to skin.

c. Do not use or mix together with acidic solutions.

Ammonia reacts with an acid to give ammonium salt and thus the cleanser
loses its cleaning ability. / A lot of heat will be evolved in neutralization.

d. Ammonia dissolves in water to give hydroxide ions.

The hydroxide ions hydrolyze the oil to give soap.

The soap formed emulsifies the oil and thus the oil can be removed readily.

e. Concentrated sodium hydroxide solution attacks glass.

f. Advantage: Soap is biodegradable / seldom causes skin allergies / non-toxic.

Disadvantage: Soap cannot function well in hard water.

g. i. Any one of the following:

‧ Plastic is chemically inert.

‧ Plastic bottles are not easily broken.

‧ Plastic bottles are light in weight.

‧ Plastic can be moulded easily.

‧ Plastic is cheap.

ii. Any one of the following:

‧ Polythene

‧ Polypropene

‧ Polystyrene

‧ Polyvinyl chloride
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
29. a. i

ii.

iii. The ester linkage can be hydrolyzed in the presence of acid / alkali.

b. i.

ii.

iii. There are strong hydrogen bonds between chains of Twaron

while there are only van der Waals’ forces between chains of polymer X.

30. a. Amine functional group and carboxyl group

b. i. ii iii

c. i. Phenylalanine molecule contains one carbon atom bonded to four different

groups of atoms.

ii.

iii. The enantiomers rotate the plane of polarization of a beam of plane-polarized

light in opposite directions and equal angles.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
d. i. Condensation reaction

ii.

OR

iii. Peptide link or amide functional group

31. a. i. Conc. HCl / conc. NaOH

Heat under reflux

ii. Amino acids

iii. The correct structure for one of the amino acids, depending on the reagent
suggested in concentrated HCl used:

OR Concentrated NaOH used:

b. i. Stereoisomers have their atoms linked in the same way,

but they differ in the spatial arrangement of their atoms.

ii.
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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
32. Add water to the liquids.

Only CH3(CH2)7OH is immiscible with water.

Warm the remaining three compounds with acidified potassium dichromate solution
separately. Only CH3CH2OH turns the orange dichromate solution green.

Any one of the following:

‧ Mix the remaining two compounds with phosphorus pentachloride separately.

Only (CH3)3COH gives steamy fumes of hydrogen chloride.

‧ Warm the remaining two compounds with ethanoic acid in the presence of
concentrated sulphuric acid separately.

Only (CH3)3COH gives a sweetish / pleasant smell.

(3 marks for organization and presentation)

33. Add concentrated hydrochloric acid slowly into a separating funnel containing
2-methylbutan-2-ol while shaking until the acid is in excess.

Leave the separating funnel plus its contents in the fume cupboard for about 20
minutes.

Shake it gently at intervals.

Allow the layers in the separating funnel to separate. Run off and discard the
lower aqueous layer.

Add sodium hydrogencarbonate solution to the organic layer in order to neutralize

the excess hydrochloric acid used.

Allow the layers to separate. Run off and discard the lower aqueous layer.

Transfer the organic layer into a conical flask. Add enough anhydrous calcium chloride
and swirl the flask.

Decant the organic product into a distillation flask. Carry out fractional distillation.

Collect 2-chloro-2-methylbutane in the temperature range of 84 – 87oC.

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Suggested answer of Assignment XI (structured questions) : Chemistry of carbon compounds
34. a. i. Amide functional group

ii. CH3COOH

b. i. Condensation reaction

ii.

c. The tripeptide glutathione stored in the liver can detoxify the principal toxic
metabolite of paracetamol. A high dose may deplete the glutathione.

As a result, the toxic metabolite accumulates and may cause irrepairable damage.

d. i. Amine functional group

Ester functional group

ii. Hydrolysis

CH3CH2OH