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Chemistry

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Organic Chemistry

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α-Carbon Chemistry: Enols, Enolates, and Enamines

Ketone Aldol Condensation Under Acid

Description

Ketone aldol condensation under acidic conditions leads to an unsaturated carbonyl product. The reaction starts with acid protonating the ketone to form a protonated ketone. Then the conjugate base of the acid removes the alpha carbon proton and forms the enol, a neutral molecule with a carbon-carbon double bond and an alcoh...

Transcript

Aldol addition reactions of aldehydes or ketones can also be catalyzed by acids.

Recall that the aldol addition reaction is unfavorable for ketones under basic conditions. However, an acid shifts the equilibrium forward to exclusively form the unsaturated carbonyl product instead of an aldol.

Here, the carbonyl group is first activ...

Tags

Enol Formation MechanismKetone ProtonationBeta Hydroxy KetoneUnsaturated Carbonyl ProductOrganic Reaction MechanismAcid Catalyzed DehydrationNucleophilic AdditionCyclohexanone ChemistryAldol Condensation