Formation of Halohydrins (Addition of Hal2 and H2O to Alkenes)

Step 2: Nucleophilic Ring-opening

The ring-opening reaction is facilitated by relief of ring strain in the 3-membered cyclic bromonium ion.  A new carbon-oxygen bond is formed by an SN2 reaction on the electrophilic carbon atom in which the nucleophile (water) approaches from the side opposite from the departure of a leaving group (bromine).

Step 1 - Step 2 - Step 3
 

 

Overall Reaction