CONFIDENTIAL 2 AS/DEC 2019/CHM301

PART A

QUESTION 1

Consider the following compounds.

CH3CH2OH (CH3)3C(OH)
Compound A Compound B

a) Name compound A and compound B according to IUPAC system.

(2 marks)

b) Identify compound A and compound B as primary, secondary ortertiary alcohol.

(2 marks)

c) State any chemical test to distinguish between compound A and B.

(1 mark)

QUESTION 2

Predict the product(s) formed when methyl butanoate reacts with the following compounds.
a) Propanamine
(3 marks)

b) Excess methyl magnesium bromide with water

(2 marks)

QUESTION 3

a) Construct a chemical equation for the hydrolysis of N-methyl propanamide in the

presence of sulphuric acid.
(4 marks)

b) Predict the classes of N-methyl propanamide as primary, secondary ortertiary amide.

(1 mark)

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QUESTION 4

A compound of cycloalkene can be prepared through dehydration of 2-methylcyclohexanol.

a) Outline stepwise mechanism of the reactions.

(3 marks)

b) Determine the major and minor products formed.

(2 marks)

QUESTION 5

Predict the name for the following compound,

a)

(5 marks)

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QUESTION 6

0 0 0 0
x X x x
H3C CI H3C NH2 H3C OCH3 H3C OH

Compound F Compund G Compound H Compound J

a) List the above compounds according to their reactivity from the lowest to the highest
towards nucleophilic acyl substitution.
(2 marks)

b) State a suitable reagent required to convert compound F to compound G, H and J

respectively.
(3 marks)

QUESTION 7

Consider the following compound.

O O
X X
H3C O CH2CH3

Compound K

a) Predict the functional group of compound K.

(1 mark)

b) Compound K can be prepared from acid chloride. Express a chemical equation for the
reaction.
(3 marks)

c) Give the IUPAC name for compound K.

(1 mark)

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CONFIDENTIAL AS/DEC 2019/CHM301

QUESTION 8

COOH COOH

NH2 N02
Compound L Compound M

a) Discuss the acidity of compound L and compound M.

(3 marks)

b) Give the IUPAC name for compound L and compound M.

(2 marks)

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 CONFIDENTIAL 6 AS/DEC 2019/CHM301

PARTB

QUESTION 1

Compound Q with a molecular formula C4H80 shows a negative Iodoform test. Compound
Q can be prepared from the oxidation of compound P by PCC. When compound Q reacts
with reagent X and W, compound U and R are produced, respectively. Compound Q also
undergoes chemical reactions to produce compound S and T, respectively.

Compound P

PCC

OH
CH3CH2CH2CH3 .*—"tX (C4Ha0) _RaagentV^ HQ^
H * z J
Compound U Compound Q Compound R
CH3CH2MgBr / \ HCN
H20

Compound T Compound S

a) Sketch the structural formulas of compound P, Q, S and T.

(4 marks)

b) Predict reagent X and W.

(3 marks)

c) Determine the chemical test to differentiate compound P and T.

(3 marks)

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 CONFIDENTIAL AS/DEC 2019/CHM301

QUESTION 2

Consider the following reactions scheme.

"^s

Compound P

o O
V-?
/ <
CI
;NH3
Compound K + L -*-
Reaction I
a Compound M
+

Compound N
Aniline

LiAIH4, H20

Compound R

a) Illustrate the structural formulas of compound K, L, M, N and R.

(5 marks)

b) Illustrate the mechanism involved in reaction

(2 marks)

c) Outline the synthetic sequences of Aniline from compound P.

(3 marks)

END OF QUESTION PAPER

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