Octet / Reactions
Hofmann Rearrangement
Hofmann Rearrangement (Rearrangement.) Converts CC(=O)N to CN using Br₂, NaOH. Conditions: Aqueous base.
Rearrangement
Reaction details
Name
Hofmann Rearrangement
Type
Rearrangement
Starting Material
CC(=O)N
Product
CN
Reagents
Br₂
NaOH
Conditions
Aqueous base
Mechanism
- Smiles
CC(=O)N
- Description
Amide starting material
- Smiles
CC(=O)NBr
- Description
N-bromoamide forms
- Smiles
CN
- Description
Migration and hydrolysis gives amine (one carbon less)
Tips
Amide → Amine (loses one carbon as CO₂)
Similar to Curtius but from amide
R migrates with retention of configuration
Also called Hofmann degradation
Related Reactions
curtius-rearrangement
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