Octet / Reactions
Hell-Volhard-Zelinsky Reaction
Hell-Volhard-Zelinsky Reaction (Substitution.) Converts CCC(=O)O to CC(Br)C(=O)O using Br₂, PBr₃ or P.
Substitution
Reaction details
Name
Hell-Volhard-Zelinsky Reaction
Type
Substitution
Starting Material
CCC(=O)O
Product
CC(Br)C(=O)O
Reagents
Br₂
PBr₃ or P
Mechanism
- Smiles
CCC(=O)O
- Description
Carboxylic acid
- Smiles
CCC(=O)Br
- Description
Acid bromide formed (enolizable)
- Smiles
CC(Br)C(=O)O
- Description
α-Bromination then hydrolysis → α-bromo acid
Tips
α-Bromination of carboxylic acids
Goes through acid bromide intermediate
Br₂/P or Br₂/PBr₃
Product useful for further substitution
This is one row of the Reaction roadmap sheet - print all 83 reactions on one page.