Ch_322a_10.013

Ch_322a_10.013 - Radical Additions to Alkenes The...

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Radical Additions to Alkenes The Anti-Markovnikov Addition of HBr Before 1933, the addition of HBr to alkenes gave confusing results. In contrast to HCl, which always gave the Markovnikov addition product, the HBr reaction sometimes gave the anti-Markovnikov product. CH 3 CH=CH 2 + HCl CH 3 CHCH 3 Cl isopropyl chloride (Markovnikov Product) CH 3 CH=CH 2 + HBr sometimes CH 3 CH 2 CH 2 Br propyl bromide (Anti-Markovnikov Product)
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The Role of Organic Peroxides In 1933, Morris Kharasch and Frank Mayo (U of Chicago) reported that the erratic behavior of HBr was due to trace amounts of organic peroxides , sometimes present as a contaminant in the alkenes, that initiated a competing free radical chain addition . R-O-O-R :: : R-O-O-H organic peroxide organic hydroperoxide They showed the anti-Markovnikov addition product could be suppressed by adding small amounts of free radical "traps" that inhibited the propagation of the free radical chain reaction.
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Ch_322a_10.013 - Radical Additions to Alkenes The...

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