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When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
Question

This is my attempt at answering the question: My solution

I would like to know whether I have drawn the correct carbocation forms of each of these bromo-compounds and if my reasoning is sound.

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Yes, both your answers and reasoning are correct. For the second compound a slight ambiguity might arise, because the $\mathrm{sp^2}$-hybridized carbons show $\text{-I}$ effect which would destabilize the carbocation, however considering the fact that there are not only $\ce{2 Me}$— groups attached which show $\text{+I}$, they are also closer than one of the $\mathrm{sp^2}$- carbons, it is quite natural that the net inductive effect would stabilize it.

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  • $\begingroup$ Got it. Thanks for clarifying. $\endgroup$ May 18 '21 at 19:20

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