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    Solvolysis of benzyl chloride

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    The solvolysis of benzyl chloride proceeds via a carbocation intermediate and occurs more rapidly than the solvolysis of 2-chloro-norbornane and tertiary butyl chloride. However, primary carbocations are the least stable and most difficult to form so that reactions involving these carbocations are usually slow. The best explanation for this apparent contradiction is:

    a. the pi electrons of the benzene ring stabilize the carbocation.
    b. the benzene ring exerts a strong inductive effect
    c. induced-dipole/induced-dipole interactions of the nonpolar benzene ring stabilize the carbocation
    d. the positive charge on the carbocation can be resonance stabilized by the benzene ring

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    Problem: The solvolysis of benzyl chloride proceeds via a carbocation intermediate and occurs more rapidly than the solvolysis of 2-chloro-norbornane and tertiary butyl chloride. However, primary carbocations are the least stable and most ...

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    This posting answers a multiple choice question about solvolysis of benzyl chloride.

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