AS/JAN 2013/CHM624

UNIVERSITI TEKNOLOGI MARA

FINAL EXAMINATION

COURSE ADVANCED ORGANIC CHEMISTRY

COURSE CODE CHM624
EXAMINATION JANUARY 2013
TIME 2 HOURS

INSTRUCTIONS TO CANDIDATES

1 This question paper consists of five (5) 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

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

This examination paper consists of 4 printed pages

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL 2 AS/JAN 2013/CHM624

QUESTION 1

a) Briefly explain what is meant by the following terms:

i) Diastereoselectivity
ii) Enantiomers
iii) Homotopic
iv) Regioselectivity
v) Racemic mixture

(15 marks)

b) Identify the general class of each of the following reactions (e.g. oxidation,
electrophilic addition, elimination or substitution etc).

CH3CI/AJCI3 ^-^CH3 N V " H2 /acid

° > HO
in)
->~

0 0H
NaBH4
iv
ii) RAR ^ R R heat

(8 marks)

QUESTION 2

a) Using illustration, explain the formation of two products, Q(major) and R(minor) when
compound P is treated with hydrogen in the presence of platinum as catalyst.

(5 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL 3 AS/JAN 2013/CHM624

b) Classify the types of selectivity (diastereoselectivity, diastereofacial selectivity,

enantiofacial selectivity, regioselectivity etc) operating in each of the following. Give
explanation for the types of selectivity that you have chosen.
OH O
0 0 I II
yeast reduction ^ ^ ^ ^ o^

•c [J
NH, NH2 NH2

6 nitration
^ fWj +
HN03/H S0 2 4
^ > \
l

N0 2
J
^r\ ^N02

Me
Me
i 1.CH3MgBr f
H H
"') / \ ^ *~ P h - ^ ^ ^ major product
+
H 2. H30 Me OH
0 0
/ \\ Claisen rearrangement /—x \

(8 marks)
QUESTION 3

Provide a reasonable mechanism for the following transformations.

-OH Swern oxidation / ^ \ / \ ^

o r II *- H
reagents: DMSO, (C0CI)2, triethylamine

O
oII Bayer Villiger II QM
M)
H3C-ACH3 *- H3C^O' 3
^ a ^ H

reagent: MCPBA MCPBA 0

Peterson olefination R2 .-^ Ov

iii) Me.„.^. O^ *• ^
<Si n Ri o
Me Me 0
O
reagents: a. LDA/THF b. N
R2 R-,

(12 marks)

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL

CONFIDENTIAL 4 AS/JAN 2013/CHM624

QUESTION 4

Suggest suitable reagent(s) that can be used for the following transformation.
OH OH

i) r X
^ .o

ii)

?
i) >-
O O "O
0 o
?
^_ /-. .OH
iv)

(12 marks)

QUESTION 5

a) Using appropriate example, explain the difference between kinetic and thermodynamic
enolates.
(4 marks)

b) Explain the role of protection of functional groups in organic synthesis. Suggest any
protecting group(s) (and de-protecting group) and reagent(s) that can be used to carry
out the following transformation.

reagents?

O N protecting group(s) i
H

(6 marks)

END OF QUESTION PAPER

© Hak Cipta Universiti Teknologi MARA CONFIDENTIAL