Octet / Reactions
Halohydrin Formation
Halohydrin Formation (Addition.) Converts CC=CC to CC(O)C(Br)C using Br₂/H₂O (or Cl₂/H₂O). Stereochemistry: Anti addition.
Addition
Reaction details
Name
Halohydrin Formation
Type
Addition
Starting Material
CC=CC
Product
CC(O)C(Br)C
Reagents
Br₂/H₂O (or Cl₂/H₂O)
Mechanism
- Smiles
CC=CC
- Description
2-Butene
- Smiles
CC1C(C)Br1
- Description
Bromonium ion forms
- Smiles
CC(O)C(Br)C
- Description
Water (nucleophile) opens ring at more substituted carbon
Stereochemistry
Anti addition
Regiochemistry
OH on more substituted carbon (Markovnikov-like)
Tips
Water is nucleophile, not halide
Product can be converted to epoxide with base
Mechanism shown for Br₂; Cl₂ works analogously
Related Reactions
halogenation-alkene
epoxidation
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