The electrophilic addition of halogens to alkenes in aqueous media follows a Markovnikov-like regioselectivity where the hydroxyl group attaches to the more substituted carbon and the halogen to the less substituted carbon, driven by resonance stabilization of the cyclic bromonium ion intermediate. This process operates under strict stereoselective conditions characterized by anti-addition, resulting from nucleophilic attack on the bridged intermediate rather than the initial alkene double bond. The reaction proceeds via a three-membered cyclic haliranium species that directs water to the carbon capable of supporting partial positive charge character through resonance structures involving secondary or tertiary carbocation-like intermediates.
The electrophilic addition of halogens to alkenes in aqueous media follows a Markovnikov-like regioselectivity where the hydroxyl group attaches to the more substituted carbon and the halogen to the …