Master Organic Chemistry Reaction Guide

Substitution with accompanying alkyl shift

Description: 1,2-alkyl shifts can occur during substitution reactions if an unstable carbocation is formed adjacent to a quaternary carbon.
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2 thoughts on “Substitution with accompanying alkyl shift

  1. in fourth example why secondary carbocation that is formed through ring expansion while tertiary carbocation can form by hydride shift from adjacent carbon

    thank you so much

    1. Great question. The hydride shift product could form as well. This is more of a textbook question, not an actual experiment. In practice you’d probably see both occur to some extent.

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