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Question

Which is expected to react most readily with bromine in presence of sunlight?

A
CH3CH2CH3
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B
CH2=CH2
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C
CHCH
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D
CH3CH=CH2
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Solution

The correct option is D CH3CH=CH2
Bromine in presence of sunlight will undergo free radical bromination reaction.
Addition of Br across double and triple bond does not happens in the presence of sunlight because it goes by free radical mechanism.
The compound forming stable radical ion will readily react with Br.
In compound (d), the formed radical is allylic. This radical is stabilised by delocalisation of π electrons. Hence, it the most stable radical and readily react with bromine.

Compound (a) gives less stable primary radical.
Compound (b) gives unstable vinylic radical.
Compound (c) gives unstable alkynyl radical.


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