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Chemistry

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Organic Chemistry

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α-Carbon Chemistry: Enols, Enolates, and Enamines

Enol Reactions at the Alpha Carbon

Description

Enols are compounds with a hydroxyl group attached to a carbon-carbon double bond. They are also called vinyl alcohols. In carbonyl compounds that have an alpha hydrogen, the keto form and the enol form stay in equilibrium through keto-enol tautomerism.

In most cases, the keto tautomer is more co...

Transcript

Enols, the tautomers of carbonyl compounds, are nucleophilic in nature owing to their electron-rich double bonds.

In addition, the electron-donating resonance effect of the adjacent hydroxyl group leads to substantially greater electron density on the α carbon, making it more reactive than the corresponding alkene.

Enols are key re...

Tags

Keto Enol TautomerismEnol FormationAlpha Carbon NucleophilicityAcid Base CatalysisDeuterium ExchangeRacemization MechanismCarbonyl HalogenationVinyl Alcohol StructureConjugation EffectsIntramolecular Hydrogen Bonding