5

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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.

lazearoundallday
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  • Can you add the entire question with the answer too? Or you just have to form the carbocation? – Swadhin May 23 '21 at 08:36
  • As comment above. However carbocation re-arrangement is a real thing. Though this example isn't even what is commonly intended by the term. It is not clear if you where introduced to the argument. I can't believe that was done by this example, though. – Alchimista May 23 '21 at 08:45
  • @RandomQuark There is no problem statement given in my book. I am just supposed to form the carbocation. And I have stated the answer as well. – lazearoundallday May 23 '21 at 10:04
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    I don't know if it's actually a rearrangement or more of several resonance structures of the same species. – S R Maiti May 23 '21 at 10:21
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    @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. – Alchimista May 23 '21 at 10:42
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    @Alchimista Yes I agree with you. I think OP is confusing resonance with rearrangement (which has to involve movement of whole atoms) – S R Maiti May 23 '21 at 10:45
  • I find some similarity in this case and this one- https://en.wikipedia.org/wiki/Neighbouring_group_participation, see NGP of an alkene, but I'm unable to figure out the exact answer. – Swadhin May 23 '21 at 13:01
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    This is not a rearrangement, they are resonance structures of a so-called "non-classical" carbocation https://en.wikipedia.org/wiki/2-Norbornyl_cation – orthocresol May 23 '21 at 13:20
  • @orthocresol Thanks for the link. I think I found my answer. – lazearoundallday May 30 '21 at 04:42
  • @ShoubhikRMaiti According to the link provided by orthocresol, I believe you are right. I asked my teacher about it yesterday, who said that its called 'Wagner-Meerwein Rearrangement'. Now that I have gone through the link, I am convinced it is just a depiction of the resonance structures. – lazearoundallday May 30 '21 at 04:44
  • Yes it is a depiction of several resonance structures, it's definitely not Wagner-Meerwein rearrangement, because that involved movement of an H. – S R Maiti May 30 '21 at 08:48

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