The addition of HBr to propene, MeCH = CH2(1), under polar conditions (in absence of peroxide) yields 2-bromopropane. However, in the presence of peroxides or the addition proceeds via a rapid’chain reaction to yield 1-bromopropane. This addition of HBr in presence of peroxide is generally referred to as the peroxide effect leading to anti-Markownikov addition. This difference in orientation of HBR addition is due to the fact that in the first (polar case) the reaction is initiated by H+ and proceeds Via the more stable (secondary) carbocation while in second (radical) case it is initiated by Br• and proceeds via the more stable (secondary radical).
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