Octet / Reactions
Beckmann Rearrangement
Beckmann Rearrangement (Rearrangement.) Converts CC(c1ccccc1)=NO to CC(=O)Nc1ccccc1 using H₂SO₄, PCl₅, SOCl₂. Conditions: Acidic conditions, heat.
Rearrangement
Reaction details
Name
Beckmann Rearrangement
Type
Rearrangement
Starting Material
CC(c1ccccc1)=NO
Product
CC(=O)Nc1ccccc1
Reagents
H₂SO₄
PCl₅
SOCl₂
Conditions
Acidic conditions, heat
Mechanism
- Smiles
CC(c1ccccc1)=NO
- Description
Oxime starting material (from ketone + NH₂OH)
- Smiles
CC(c1ccccc1)=NO
- Description
Protonation of OH, water leaves
- Smiles
CC(=O)Nc1ccccc1
- Description
Group anti to leaving group migrates → amide
Tips
Oxime → Amide
Group ANTI to hydroxyl group migrates
Used industrially for nylon-6 synthesis (cyclohexanone oxime → caprolactam)
Stereospecific: geometry of oxime determines product
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