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I am trying to figure out the product of this reaction. I initially thought that a carbocation would be formed at where the chlorine leaves from:

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But according to the answer stated by the textbook, it should be this:

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But why does this rearrangement have to occur? Isn't the carbocation quite stable already? Any help would be appreciated.

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  • $\begingroup$ Can you add the entire question with the answer too? Or you just have to form the carbocation? $\endgroup$
    – Swadhin
    May 23, 2021 at 8:36
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    $\begingroup$ I don't know if it's actually a rearrangement or more of several resonance structures of the same species. $\endgroup$
    – S R Maiti
    May 23, 2021 at 10:21
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    $\begingroup$ @ShoubhikRMaiti that it what I also think and said above. Out of nothing this is a difficult exercise. It is a kind of hyoerconjugation complicated by the visual. $\endgroup$
    – Alchimista
    May 23, 2021 at 10:42
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    $\begingroup$ @Alchimista Yes I agree with you. I think OP is confusing resonance with rearrangement (which has to involve movement of whole atoms) $\endgroup$
    – S R Maiti
    May 23, 2021 at 10:45
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    $\begingroup$ This is not a rearrangement, they are resonance structures of a so-called "non-classical" carbocation en.wikipedia.org/wiki/2-Norbornyl_cation $\endgroup$
    – orthocresol
    May 23, 2021 at 13:20

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