Master Organic Chemistry Reaction Guide

Additions to alkenes accompanied by 1,2-hydride shifts

Description: When secondary (or primary) carbocations are formed, adjacent to a more substituted carbon, hydrogen atoms can shift. This leads to formation of a more stable carbocation.

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Comment section

8 thoughts on “Additions to alkenes accompanied by 1,2-hydride shifts

  1. Will the predominant product be the hydride shift mechanism? How much more energetically favorable is this product?

  2. Hi James.

    For example 3, why is the Cl bonded to C3 and not C2. Is it due to the hydride Shift? If so why?
    Is it because although both C2 and C3 and secondary carbons, the R group bonded to C3 is a benzene (bigger and more stable group)?


    1. The benzylic carbocation (carbocation adjacent to benzene ring) is more stable than an ordinary secondary carbocation due to resonance stabilization.

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