In the Pinacol-Pinacolone rearrangement, a methyl group migrates from an adjacent carbon to a tertia — Reaction Mechanism Chemistry Question
Question
In the Pinacol-Pinacolone rearrangement, a methyl group migrates from an adjacent carbon to a tertiary carbocation instead of a hydride. Why does this reaction violate standard migratory rules?
Answer: A
💡 Solution & Explanation
Thermodynamic stability overrides migratory aptitude. A shift that places the positive charge adjacent to an oxygen atom allows for massive resonance stabilization via back-bonding, forming a stable $C=O$ double bond.
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