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Generally, the observed migratory aptitude for carbocation rearrangement is (as given in various books) :

$$\ce{H- > Ph- >CH_3-}$$

But the fact is that the carbocation at the benzylic carbon is more stable.

This is counter-intuitive, so what is a reasonable explanation for this?

Pritt says Reinstate Monica
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Arvind Tiwari
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    @JaideepKhare You aren't aware of the \ce notation for chemical equations. Do check out https://chemistry.meta.stackexchange.com/questions/86/how-can-i-format-math-chemistry-expressions-here before suggesting wrong edits – Pritt says Reinstate Monica May 22 '17 at 09:16
  • @PrittBalagopal Thanks, I wasn't knowing about that notation of chemical equations., (I am mostly active on Math SE.)I'll take care next time. – Jaideep Khare May 22 '17 at 09:20
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    https://chemistry.stackexchange.com/questions/31599/migratory-preference-in-a-rearrangement-involving-carbocations – Mithoron May 22 '17 at 16:40

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