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Haloalkanes And Haloarenes

Question
CBSEENCH12008012

Write the resonance structure of chlorobenzene. Why is chlorobenzene less reactive than chloromethane towards nucleophiles?

Solution

Resonance structure of chlorobenzene.

Chlorobenzene are less reactive towards nucleophillic reaction due the following reason:
In chlorobenzene the electron pairs are in conjugation with pi electrons of the ring. Thus, C-Cl bond accquires a partial double bond character due to resonance. As a result, the bond cleavage in haloarene is diffcult than chloromethane.