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Question

The reactivities of methyl chloride, propyl chloride and chlorobenzene are in

the order

[KCET 1988]

A

Methyl chloride > propyl chloride > chlorobenzene

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B

Propyl chloride > methyl chloride > chlorobenzene

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C

Methyl chloride > chlorobenzene > propyl chloride

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D

Chlorobenzene > propyl chloride > methyl chloride

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Solution

Based on the study of hyperconjugation and inductive action, propyl carbocation will be more stable than methyl carbocation. More is the number of methyl groups, more will be the extent of hyperconjugation due to more number of hydrogen atoms and inductive effect, so propyl carbocation is more stable due to delocalization of electrons Therefore, methyl chloride will be more reactive than propyl chloride in terms of reactivity.

In contrast to methyl chloride, chlorobenzene is stabilized by resonance. Chlorobenzene is, therefore, less reactive and more stable.

So, the order becomes: methyl chloride> propyl chloride> chlorobenzene

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