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Addition of Weaker Nucleophiles to Aldehydes/Keytones


Hydrate formation


Hemiacetal formation


Acetal formation


CAN’T use a base
cyclic acetals



Nitrogen Nucleophiles with Primary Amines



Nitrogen Nucleophiles with Secondary Amines


Reductive Amination: Two Step Sequence

A reaction process that involves the conversion of carbonyl compounds to amines through the addition of ammonia or amines followed by reduction.
Reductive Amination: One Step Sequence


Wolff-Kishner Reduction


Enolate Formation


Thermodynamic Enolate

Kinetic Enolate

Enol formation


Enolate Alkylation


Aldol Condensation


Higher temperatures, longer reaction times, higher concentration of base
Acid-Catalyzed Aldol Condensation

Crossed Aldol Condensation

1, 2 addition


1, 4 addition


Gilman Reagent: Conjugate Addition


Michael Addition: Enolate Addition


Robinson Annulation

Michael Addition + Aldol Condensation
