Why is chlorobenzene less reactive towards nucleophilic substitution as compared to ethyl chloride?

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Text Solution

Solution : In the molecules of benzyl chloride, the electron pairs on the chlorine atom are not in a position to conjugate with the `pi`-electrons of the ring. <br> <img src="https://d10lpgp6xz60nq.cloudfront.net/physics_images/MBD_EM_CHE_XII_C10_E03_029_S01.png" width="80%"> <br> Whereas electron pairs on the chlorine atom are in conjugation with the `pi`-electrons of the ring in the molecules of chlorobenzene. Consequently, the C-Cl bond in chlorobenzene acquires some double bond character, which is not present in benzyl chloride. As a result, the reactivity of benzyl chloride is more than the chlorobenzene.

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