Master Organic Chemistry Reaction Guide

Substitution (SN1) with hydride shift

Description: 1,2-hydride shifts can occur during substitution reactions if an unstable carbocation is formed next to a tertiary carbon.

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Comment section

2 thoughts on “Substitution (SN1) with hydride shift

  1. Hi! Thanks for this great website. The question is… in the ‘quiz yourself 1’, why does not occur the alkyl shift?

    1. Hi! – generally speaking, H migrates preferentially to alkyl; mostly because it’s smaller, and it doesn’t have as many potential conformations that can create steric obstacles to migration.

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