Octet / Reactions
Enamine Formation
Enamine Formation (Carbonyl.) Converts CC(=O)CC to CC(=CN(C)C)C using R₂NH (2° amine), acid catalyst. Conditions: Remove water (Dean-Stark).
Carbonyl
Reaction details
Name
Enamine Formation
Type
Carbonyl
Starting Material
CC(=O)CC
Product
CC(=CN(C)C)C
Reagents
R₂NH (2° amine)
acid catalyst
Conditions
Remove water (Dean-Stark)
Mechanism
- Smiles
CC(=O)CC
- Description
2-Butanone (ketone)
- Smiles
CC(=CN(C)C)C
- Description
Enamine (N analog of enol)
Tips
Secondary amine + ketone → Enamine
Enamines are nucleophilic at β-carbon
Stork enamine synthesis: enamine + electrophile → α-substituted ketone
Hydrolysis regenerates ketone
Related Reactions
aldol-addition
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