Octet / Reactions
Henry Reaction (Nitroaldol)
Henry Reaction (Nitroaldol) (Addition.) Converts CC=O to CC(O)C[N+](=O)[O-] using R-NO₂, base (NaOH, Et₃N).
Addition
Reaction details
Name
Henry Reaction (Nitroaldol)
Type
Addition
Starting Material
CC=O
Product
CC(O)C[N+](=O)[O-]
Reagents
R-NO₂
base (NaOH, Et₃N)
Mechanism
- Smiles
CC=O
- Description
Aldehyde
- Smiles
C[N+](=O)[O-]
- Description
Nitroalkane: α-H is acidic (pKa ~10)
- Smiles
CC(O)C[N+](=O)[O-]
- Description
Nitronate anion attacks aldehyde → β-nitro alcohol
Tips
Like aldol but with nitroalkane
Product: β-nitro alcohol
Can dehydrate to nitroalkene
NO₂ can be converted to many groups (amine, carbonyl, etc.)
Related Reactions
aldol-addition
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