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Benzyl chloride undergoes nucleophilic s...

Benzyl chloride undergoes nucleophilic substitution much more easily than chlorobenzene. Explain. 

Text Solution

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Benzyl chloride undergoes nucleophilic substitution readily via resonance stabilised benzyl carbocation.

On the other hand C-Cl bond in benzene has partial double bond character due to resonance and hence is difficult to cleave.
Hence, benzyl chloride undergoes nucleophilic substitution much more easily than chlorobenzene.
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Knowledge Check

  • Towards, nucleophilic substitution chlorobenzene is

    A
    More reactive than ethyl chloride
    B
    More reactive than isopropyl chloride
    C
    As reactive as methyl chloride
    D
    Less reactive than benzyl chloride

  • Which of the following under go nucleophilic substitution faster than that of chlorobenzene

    A
    B
    C
    D

  • Which species will undergo electrophilic substitution reaction most easily?

    A
    Ph-OH
    B
    Ph-SH
    C
    Ph-O-
    D
    Ph-S-

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    How many of the following does not undergo nucleophilic substitution easily under normal conditions

    Give the nucleophilic substitution mechanism with allylic and benzylic halides?

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