Organic Compounds Containing Halogens Question 141

Question: Among the following, the one which reacts most readily with ethanol is

[AIIMS 2004]

Options:

A) p-nitrobenzyl bromide

B) p-chlorobenzyl bromide

C) p-methoxybenzyl bromide

D) p-methylbenzyl bromide

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Answer:

Correct Answer: C

Solution:

Due to the presence of electron rich methoxy group (+I) at p-position the polarity increase on C-X bond by which it becomes more reactive towards nucleophillic attack of ethanol, p-nitro and chloro are electron deficient group decrease the polarity of C-X bond. Hence by them it become difficult to react with ethanol due to less polarity. Methyl group is less electron rich than methoxy group.