THE LUSAKA APEX MEDICAL UNIVERSITY

FACULTY OF PREMEDICAL SCIENCES

CH 2032 - ORGANIC CHEMISTRY I TEST II

MARKING KEY 50 MARKS

SECTION A (3 MARKS EACH)

QUESTION ONE

QUESTION TWO

QUESTION THREE

QUESTION FOUR

QUESTION FIVE

D Accept: C

QUESTION SIX

C
 SECTION B

QUESTION SEVEN

CH3 CH3 CH3

+
CH3 CH C CH3 + HBr CH3 CH C CH3 CH3 CH C CH3

HO CH3 Br H 2O CH3 CH3

+ H 2O

Br

CH3

CH3 CH C CH3

Br CH3

Product 1

CH3 CH3 CH3

+
CH3 CH C CH3 + HBr CH3 CH C CH3 CH3 CH C CH3

HO CH3 Br H 2O CH3 CH3

+ H 2O

+
H

CH3

CH2 CH C CH3

CH3
Product 2

-2-
 CH3 CH3 CH3
+
CH3 CH C CH 3 + HBr CH3 CH C CH 3 CH3 CH C CH 3

HO CH3 Br H 2O CH3 CH3

+ H 2O

1,2-CH3 shift

CH3 CH3 CH3

+
CH3 CH C CH 2 + CH3 C C CH3 CH3 CH C CH 3

CH3 CH3
H+ CH3

Product 4 or Product 3 or
product 3 product 4

CH3 CH3 CH3

+
CH3 CH C CH3 + HBr CH3 CH C CH3 CH3 CH C CH3

HO CH3 Br H 2O CH3 CH3

+ H 2O

1,2-CH3 shift

CH3 Br CH3
Br +
CH3 CH C CH3 CH3 CH C CH3

CH3 CH3

Product 5

-3-
QUESTION EIGHT

a) Products of the reaction.

H H
H Br Br
H
Br Br
1,4 - Addition product 1,4 - Addition product
1,2 - Addition product 1,2 - Addition product Minor product
Second major product Minor product The major product

Alternatively
Showing both alternatives, give double marks
Mechanism

+
H

+
+ + H H
H H +

20 allylic carbocation 10 allylic carbocation 30 allylic carbocation 10 allylic carbocation

Br Br Br Br

H H
H Br Br
H
Br Br
1,4 - Addition product 1,4 - Addition product
1,2 - Addition product 1,2 - Addition product Minor product
Second major product Minor product The major product

Alternatively
Showing both alternatives, give double marks

-4-
b)
CH3 CH3
-
H3C O + H3C Br H3C O CH3
CH3 CH3

Explanation:

The substrate is a 10 alkyl halide containing one carbon and hence, cannot undergo
elimination reaction. It is likely to be attacked by t-butoxide though the t-butoxide is
relatively strong hindered base.

In the second reaction, the substrate, the t-butyl halide, is highly hindered substrate and the
SN2 attack by methoxide nucleophile is less likely.

Accept any of the two or both. For both give an extra mark

-5-