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14 MECHANISMS

Alpha-Carbon Reactions

Alpha Bromination

Alpha Bromination

Acid-catalyzed halogenation at the alpha carbon.

Hell–Volhard–Zelinsky

Hell–Volhard–Zelinsky

Alpha-bromination of a carboxylic acid.

Aldol Condensation

Aldol Condensation

An enolate adds then dehydrates to an enone.

Crossed Aldol

Crossed Aldol

An aldol between two different carbonyls.

Intramolecular Aldol

Intramolecular Aldol

A ring-forming aldol condensation.

Claisen Condensation

Claisen Condensation

Two esters give a beta-keto ester.

Dieckmann Cyclization

Dieckmann Cyclization

An intramolecular Claisen forms a ring.

Alpha Alkylation

Alpha Alkylation

An enolate is alkylated by an alkyl halide.

Malonic Ester Synthesis

Malonic Ester Synthesis

Builds substituted acetic acids.

Acetoacetic Ester Synthesis

Acetoacetic Ester Synthesis

Builds substituted methyl ketones.

Decarboxylation

Decarboxylation

A beta-keto acid loses CO2 on heating.

Michael Addition

Michael Addition

Conjugate addition to an enone.

Organocuprate Addition

Organocuprate Addition

1,4-addition of a cuprate to an enone.

Robinson Annulation

Robinson Annulation

A Michael then aldol builds a new ring.