How to Compare the Carbocation Stability – Part 3

The carbocation stability is critical to the success of many reactions involving organic compounds.


The stability of a carbocation depends on multiple factors, say, its participation in resonance, presence on a substituted carbon (α─H) or existence in an aromatic ring. For every carbocation rearrangement there must be some driving force to form more stable carbocation. A rearrangement may take place via hydride/methyl shift, ring expansion and so on. 

Question:

Predict the major product(s) of the following reaction:



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Solution infographic:



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NOTE: Post updated since published

References:
(1)    Carbocation. Wikipedia. https://en.wikipedia.org/wiki/Carbocation.
(2)    
Chouhan, M. S. Advanced Problems in Organic Chemistry for JEE, 11th Ed.

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