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

Reaction of Alkenes and Bromine in Other Nucleophilic Solvents

 

Reactions of alkenes with bromine in alcohols provides 2-bromoethers by the same mechanism as formation of bromohyrins.

 

FIGURE

 

In this case a molecule of alcohol reacts as a nucleophile and causes ring opening of the cyclic bromonium ion.  Consequently the stereochemistry and regiochemistry are identical to those found in formation of bromohyrins.