Ch_322a_11.04

Ch_322a_11.04 - Synthesis of Alcohols from Alkenes...

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Synthesis of Alcohols from Alkenes Hydration of Alkenes Alkenes react with water in the presence of an acid catalyst to give alcohols. The regiochemistry of the addition reaction follows Markovnikov's rule . R-C=C-H H H +H + -H + R-C-CH 3 H + alkene +H 2 O -H 2 O R-C-CH 3 H OH 2 + -H + +H + R-C-CH 3 H OH alcohol Carbocation rearrangements may occur which limits the synthetic generality of this reaction.
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Two General Syntheses Two standard procedures for converting alkenes to alcohols with controlled regiochemistry and some degree of controlled stereochemistry are: (1) The Oxymercuration-Demercuration Procedure (Markovnikov product) (2) The Hydroboration-Oxidation Method (anti-Markovnikov product)
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There are two steps in this method: (1) Oxymercuration An alkene reacts with water in the presence of mercuric acetate, Hg(OAc) 2 , (an electrophile) in a mixture of THF and water. The role of theTHF is to help dissolve the alkene. C=C oxymercuration product
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Ch_322a_11.04 - Synthesis of Alcohols from Alkenes...

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