CONFIDENTIAL AS/DEC 2019/CHM301

UNIVERSITI TEKNOLOGI MARA

FINAL EXAMINATION

COURSE ORGANIC CHEMISTRY II

COURSE CODE CHM301

EXAMINATION DECEMBER 2019

TIME 2 HOURS

INSTRUCTIONS TO CANDIDATES

1. This question paper consists of two (2) parts : PART A (8 Questions)

PART B (2 Questions)

2. Answer ALL questions in the Answer Booklet. Start each answer on a new page.

3. Do not bring any material into the examination room unless permission is given by the
invigilator.

4. Please check to make sure that this examination pack consists of:

i) the Question Paper

ii) an Answer Booklet - provided by the Faculty

5. Answer ALL questions in English.

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO

This examination paper consists of 7 printed pages
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 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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CONFIDENTIAL 3 AS/DEC 2019/CHM301

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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