Tautomerism

Rarely Tested


Concept: Dynamic isomerism involving the migration of a mobile proton between two polyvalent atoms accompanied by a shift of a double bond.

Keto-Enol Tautomerism:

  • $$\text{R--CH}_2\text{--C(=O)--R'} \rightleftharpoons \text{R--CH=C(OH)--R'}$$
  • Enol Content Factors: Enol percentage increases with aromaticity, intramolecular hydrogen bonding, and extensive conjugation.
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