Reactions

Alkene hydrohalogenation (Markovnikov)

Abstract

Hydrohalogenation is a reaction in which a hydrogen halide (HX, where X = I, Br, or Cl) adds across the double bond of an alkene, yielding an alkyl halide.

General reaction scheme of Alkene hydrohalogenation (Markovnikov)

Keywords

Alkene, Alkyl halide, Markovnikov


Category

Alkene

Mechanism

The mechanism proceeds in two steps. First, the double bond is protonated, leading to the formation of the most stable, most substituted carbocation (Markovnikov’s rule) and releasing a halide ion (in our example, a bromide ion). Then, the bromide ion attacks the carbocation from either face, giving a racemic mixture of the corresponding alkyl bromide.

Chemical mechanism of: Alkene hydrohalogenation (Markovnikov)