Halohydrin formation reaction
From Wikipedia, the free encyclopedia
A halohydrin formation reaction is an chemical reaction in which a halogen is added to an alkene in aqueous solution to form a halohydrin. The reaction is similar to the halogen addition reaction.
The basic chemical equation for this reaction is as follows:
- C=C + X2 + H2O → X-C-C-OH
(X represents a halogen, either Cl or Br).
The reaction occurs with anti addition, leaving the newly added X and OH groups in a trans configuration.
The reaction is a form of electrophilic addition.
N-Bromosuccinimide is preferable to bromine in that fewer side-products are produced.
[edit] Reaction mechanism
In the first step, the pi bond of the alkene attacks the halogen, forming a bromonium ion. The addition of water gives the desired halohydrin with high anti stereoselectivity and Markovnikov addition preference.
