CH 2032 QUIZ II MARKING KEY

50 MARKS
QUESTION ONE.

Products
CH3 Br Br CH3 Br CH3

H2C C CH CH2 H2C C CH CH2 H2C C CH CH2

Br Br Br
.
Mechanism:

Br Br Br Br

+
+ + Br Br
Br Br +

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

Br Br Br Br

Br Br
Br Br Br
Br
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

Same product

Br
Br
The most stable

Reason: Formed from the most stable carbocation, the 30 carbocation

QUESTION TWO.

Provide the meaning of the following terms as they are used in organic chemistry.

i) Kinetically controlled product It is the product obtained at a lower

temperature, the lesser energy temperature

ii) Thermodynamically controlled It is the product obtained at a higher

temperature, the more energy temperature

QUESTION THREE.

The term aromaticity as it is used in organic chemistry

It is the minimisation of energy in a cyclic, planar, fully conjugated and containing

4n+2 pi electrons.

QUESTION FOUR

The Huckel’s rule of aromaticity.

i) For a compound to be aromatic it must be cyclic, planar, fully conjugated and
contain 4n+2 pi electrons.

ii) The benzene molecule is a nucleophile

Reason

It has a high electron π system that is a cloud of electrons in nature