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ORGANIC CHEMISTRY LANEY COLLEGE CHEM 12A Version 2.0, 9/1/06 Chapter 8 Learning Objectives and Terminology (Wade) Addition of hydrogen halides (HBr, HCl, HI) to alkenes yields alkyl halides and occurs with Markovnikov selectivity – the halide ends up on the most substituted carbon. Radical addition of HBr (only) gives anti- Markovnikovff addition (peroxide effect) to alkenes due to a change in the mechanism, which involves the addition of a bromine radical. Addition of X 2 in halogenated solvents, such as CH 2 Cl 2 or CHCl 3 , proceeds with anti addition to give 1,2- dihalides ( vicinal ). Addition of Br 2 or Cl 2 in water gives halohydrins (addition of HOX). Use of an alcohol instead of water as the solvent give halo ethers. Any addition reaction that involves addition Br 2 or Cl 2 also involves an intermediate bromonium or chloronium ion. Subsequent additions of nucleophiles to this ion occur from the “back” side and gives rise to the observed anti addition products.
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