Sodium_Borohydride_Reductio

Sodium_Borohydride_R - Sodium Borohydride Reduction 1/16/03 9:58 PM Sodium Borohydride Reduction The complement to the oxidation of alcohols is the

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Sodium Borohydride Reduction The complement to the oxidation of alcohols is the reduction of carbonyl groups. There are several reagents for this purpose but the two hydride reducing agents, NaBH and LiAlH , are widely used. The active species is hydride, :H , a form of hydrogen with a pair of electrons. We'll see that these electrons are nucleophilic. You remember the H /Pt reducing agent but it's impractical for carbonyl groups because high temperatures and pressures are required. NaBH is the less reactive of the two but is consequently more selective. LiAlH is very reactive but less discriminating in the substrates it reduces. 4 4 - 2 4 4 Notice that there is a second step to this reaction, the addition of aqueous acid. The mechanism proceeds by successive addition of hydride to the carbonyl group. The first step is as follows then the remaining three hydrides on boron react similarly. Pay special attention to the hydrogen on what used to be the carbonyl group. That
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This note was uploaded on 02/13/2011 for the course CHEM 2344 taught by Professor Slack,wu during the Spring '11 term at University of Houston.

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Sodium_Borohydride_R - Sodium Borohydride Reduction 1/16/03 9:58 PM Sodium Borohydride Reduction The complement to the oxidation of alcohols is the

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