In the Pinacol-Pinacolone rearrangement, a methyl group migrates to a tertiary carbocation instead o — Reaction Mechanism Chemistry Question
Question
In the Pinacol-Pinacolone rearrangement, a methyl group migrates to a tertiary carbocation instead of a hydride. Why does this violate standard migratory aptitude?
Answer: C
💡 Solution & Explanation
If a shift leads to a carbocation adjacent to an oxygen atom, the massive $+M$ resonance stabilization from the lone pair thermodynamically overrides standard migratory aptitude rules.
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