CHEMISTRY 962 / 3

Section A [15 marks]

Answer all questions in this section.

1 When 0.1 mole of X is burnt in excess oxygen, 17.6 g of carbon dioxide is produced. 0.1
mole X is found to react with 4.48 dm3 of bromine vapour under standard conditions. What is the
possible structural formula of X?
[Relative atomic mass: C = 12, O = 16. The molar volume of a gas is 22.4 dm3 at s.t.p.]

A CH3CH2CH2CH3
B CH3CH = CH2
C CH2 = CHCH = CH2
D CH2 = C = C = CH2

2 Which compound reacts with chlorine following the mechanisms for free radicals and
electrophilic substitution?

A CH3CH3
B CH2Cl2
C CH3CH = CH2
D C6H5CH3

3 Which of the following pairs is correct regarding the type of bond and the type of mechanism
in alkenes?

Type of bond Reaction mechanism

A Single Free radical addition

B Single Electrophilic addition
C Double Electrophilic addition
D Double Nucleophilic addition

4 The suitable reagent used to differentiate benzene from 2-hexene is

A Cl2 B HBr C H2SO4 D KMnO4

5 Which species could be an intermediate in an SN1 substitution?

A OH C
│ CN
CH3 — C — Cl +
│ H
O-
B D CH3
+ │
CH2 HOδ- C Brδ-

CH3 CH3
 2

6 In a preparation of ethene, ethanol is added a drop at a time to a heated reagent Y. To purify

the ethene, it is bubbled through a solution Z and then collected.

What could reagent Y and solution Z be?

reagent Y solution Z

A acidified K2Cr2O7 dilute NaOH

B concentrated H2SO4 dilute H2SO4
C concentrated H2SO4 dilute NaOH
D ethanolic NaOH concentrated H2SO4

7 Phenol is an important commercial chemical. Which commercial product does not use
phenol in its manufacturing?

A Food flavouring C Nylon

B Antiseptic D Dye

8 Which of the following compounds react with hydrogen cyanide, in the presence of sodium
cyanide, to give an optically active product?

A HCHO
B CH3CHO
C CH3COCH3
D CH2CH = CH2

9 Nail varnish consists of a mixture of pigments, gloss, plasticizer and adhesive dissolved in a
suitable solvent. A common solvent is a mixture of propanone and pentyl ethanoate,
CH3CO2(CH2)4CH3.

Which reagents will give a yellow or orange precipitate with this solvent?

I 2, 4 – dinitrophenylhydrazine reagent
II alkaline aqueous iodine
III Fehling’s reagent

A I, II and III
B I and II
C II and III
D I only

10 Compound S has the following properties.

(i) It reacts with water
(ii) It reacts with alcohols and phenols to form ester.

S could be

A CH3CH2Cl C CH3COCl
B CH3COOH D C6H5Cl
 3

11 The ester Q, which is used in perfumes, has the molecular formula C6H12O2. It is found that
one of the products of acid hydrolysis of compound Q gives a yellow precipitate with alkaline
aqueous iodine.

What is the structural formula of compound Q?

A CH3CO2CH2CH(CH3)2
B CH3CH2CO2CH2CH2CH3
C (CH3)2CHCO2CH2CH3
D CH3CH2CH(CH3)CO2CH3

12 Which method is able to separate benzene from a mixture of benzene and an amine?

A extracting the amine with ethanol.

B nitrating the benzene with a nitrating mixture.
C shaking the mixture with dilute aqueous alkali
D shaking the mixture with dilute aqueous acid

13 Which reagent does not react with ethanamine?

A HNO2 B NaOH
C CH3COCl D CH3CH2Cl

14 Glycine (2-aminoethanoic acid) is an optically inactive amino acid. Which of the following
compounds is formed not because of the acid-base property of glycine?

A H2NCH2COONa
B CH3OOCCH2NH2
C HOOCCH2NH3Cl
D HOOCCH2NH3OOCCH3

15 The repeating unit of a synthetic polymer is shown below.

CH3
│
— CH2 — C — CH2 — CH = C — CH2 —
│ │
CH3 CH3

Which statement about the polymer is true?

A Its monomer is CH2 = C(CH3)2

B It is a homopolymer.
C It is waterproof.
D It is stable against oxidation
 4

Section B [15 marks]

Answer any two questions in this section.

16 The reaction scheme shows the conversion of hydrocarbon P to a compound S. Compound P,

C4H8, reacts with hydrogen bromide to form compound Q, C4H9Br. When aqueous sodium hydroxide
is added to Q, compound R, C4H9OH, is formed. Compound R reacts with hot acidified potassium
manganate(VII) to form compound S, C4H8O.

(a) Compound S forms an orange precipitate with 2, 4 - dinitrophenylhydrazine and a

yellow precipitate with aqueous alkaline iodine. Draw the structural formula of S. [1 mark]

(b) Hence, identify (condensed formula) compounds Q and R. [2 marks]

Compound Q : _______________________________________________________________

Compound R : _______________________________________________________________

(c) Name the types of reactions that occur in stages II and III. [2 marks]

Stage II : ___________________________________________________________________

Stage III : __________________________________________________________________

(d) Draw the possible structures of compound P. [2 marks]

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17 (a) Write the structural formulae of the products formed when the following compound,

reacts with [4 marks]

(i) sodium metal

(ii) sodium hydroxide solution

(iii) ethanoic acid in the presence of concentrated sulphuric(VI) acid and warmed

(iv) dilute nitric(V) acid

(b) Write the structural formula of the organic products formed in the following reaction.
[4 marks]

(i)

(ii)

(iii)

(iv)
 6

Section C [30 marks]

Answer any two questions in this section.

18 (a) (i) In separate experiment, chlorine gas is bubbled into methylbenzene in the
presence of aluminium chloride. Write the mechanism for the formation of one of the compounds.
[5 marks]

(ii) Give the structural formulae of the organic products formed (if any) when
phenol and phenylmethanol are separately treated with each of the following. [2 marks]

-- Acidified KMnO4
-- Bromine water

(b) When ethylbenzene is treated with chlorine under different conditions, two isomeric
compounds, A and B, are formed. A is optically active while B is not. When A is treated with
aqueous sodium hydroxide, compound C which gives a yellow precipitate with an alkaline solution of
iodine is obtained. However, when A is treated with ethanolic potassium hydroxide, compound D
which decolourises bromine in tetrachloromethane is formed. B does not react with aqueous sodium
hydroxide or ethanolic potassium hydroxide. However, it is oxidised by hot acidified potassium
manganate(VII) solution to an acid, E. Suggest the structural formulae of C, D and E and write
equations for the reactions that take place. [8 marks]

19 (a) What do you understand by structural isomers, geometrical isomers, and enantiomers.
Ilustrate your answers for structural isomers with C3H8O, geometrical isomers with 2-butene and
enantiomers with 2-butanol. [7 marks]

(b) Compound X, C7H9N reacts with dilute hydrochloric acid to form a salt with a
formula of C7H10NCl. When X is warmed with an acidic solution of sodium nitrite, a colourless gas
and compound Y is produced. Y on oxidation produces Z, C7H6O2. Z releases carbon dioxide from
sodium carbonate.

(i) Deduce the structural formulae of X, Y and Z and write the equation for each
reactions taking place. [6 marks]

(ii) X has a structural isomer, W, which reacts with cold acidified sodium nitrite
without releasing any gas. Draw and name the structural formula of W. [2 marks]

20 (a) Suggest suitable reagents and conditions to differentiate the following pairs of
organic compounds. State the observations and write equations for the reactions involved.

(i) CH3CH2OH and CH3CH2CHO

(ii) CH3CH2NH2 and CH3CONH2 [8 marks]

(b) Terylene is a polymer formed by the condensation polymerisation from the

monomers ethane-1, 2-diol and terephthalic acid. The structures of the monomers are shown below.
 7

(i) Write an equation for the condensation polymerisation between these two
monomer form terylene. [2 marks]

(ii) Ethene can be converted to ethane-1,2-diol in a two-step reaction. Write a

reaction to show this conversion. [4 marks]

(iii) Terephthalic acid can be prepared from the oxidation of 1,4-dimethylbenzene

Name a suitable reagent for this conversion. [1 mark]

END OF QUESTION PAPER

8
CHEMISTRY 962 / 3 – MARKING SCHEME

Section A (15 marks)

Question No Answer Question No Answer

1 C 9 B

2 D 10 C

3 C 11 C

4 D 12 D

5 B 13 B

6 C 14 B

7 A 15 A

8 B

Section B (15 marks)

No Suggested answer Marks

16 (a) 1

Structure formula S
16 (b) 1
1

16 (c) Stage II : hydrolysis 1

Stage III : oxidation 1

16 (d) Structure compoud P

1
1
and

Total 7 Marks
17 (a) (i) 1
 2

17 (a) (ii) 1

17 (a) (iii) 1

17 (a) (iv) 1

17 (b) (i) 1
1

17 (b) (ii) 1

17 (b) (iii) 1

17 (b) (iv) CH3CH2COONa + CH3NH2 1

TOTAL Marks 9
Max 8

SECTION C (30 marks)

Question Explanation Marks

No.
18 (a) (i) 1

1 arrow
1 label
Carbocati
on

1 arrow
1 major
product
 3

Question Explanation Marks

No.
18 (a) (ii) With acidified KMnO4
Product Phenylmethanol

1
structural
formula
Phenol no reaction

With Bromine water

Product Phenol

1
structural
formula

Phenylmethanol no reaction

18 (b)
1
1
1

Reaction of A with aqueous sodium hydroxide:

Reaction of C with alkaline iodine:

Reaction of A with ethanolic potassium hydroxide: 1

 4

Question Explanation Marks

No.

Reaction of D with bromine:

1

Oxidation of B by hot acidified potassium manganat(VII)

Total 15
Marks

19 (a) Structural isomers are compounds which have the same molecular formula but 1
different structural formulae.

Example:
1

Geometrical isomers are compounds which have the same molecular formula 1
but are different in their spatial arrangement due to the presence of a double
bond or a cyclic structure.

Example:

Optical isomers are compounds that have the same molecular formula
but are mirror images of one another and are not superimposable. 1

Example : 2-butanol
 5

Question Explanation Marks

No.

19 (b) 1
1
1

19 (b) (ii) W is a phenylamine: 1

TOTAL 15
Marks

20 (a) (i) (i) Reagent : I2 in NaOH(aq), Condition: heat. 1+1

Observation: CH3CH2OH would form yellow precipitate of CH13 while 1
 6

Question Explanation Marks

No.
no observable change for CH3CHCHO.
1

(or Na metal at room ternperature/PCl at room temperature)

(ii) Reagent : NaOH(aq), Condition: heat 1+1

Observation: CH3CONH, liberates an alkaline gas while 1
no observable change is observed for CH3CH2NH2,
1

20(b)(i) 1

20(b)(ii) 1
Reagent
&
condition

1
product

1
reagent
&
condition

1
product

20(b)(iii) Potassium manganate( VII) 1

TOTAL 15
Marks

END OF MARKING SCHEME