Lab #4 - Sodium Borohydride Reduction

Lab #4 - Sodium Borohydride Reduction - The Sodium...

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The Sodium Borohydride Reduction of Benzil and Benzoin The reduction of benzoin produces three stereoisomeric hydrobenzoin products: a (1R, 2R) isomer, a (1S, 2S) isomer, and a meso compound. The production of these three isomers is a result of the reduction of the ketonal group with an sp 2 hybridization (planar carbon), which the hydride ion can attack on either side of the molecule. In fact, the probability of attack from either side is equal in probability, so the ratio for the isomer is 1:1:2 for (1R, 2R): (1S, 2S): meso compound. The meso compound is twice as likely to form because there are two possibilities: (1R,2S) and (1S, 2R). Benzil could produce four products including benzoin because it has 2 carbonyl that can be reduced, as opposed to benzoin which only has one carbonyl to be reduced. Possible products include benzoin and hydrobenzoin. If only one of the carbonyl ketonal group is attacked, the product is benzoin. However, excess NaBH 4 reagent promotes the further reduction of this product into a hydrobenzoin stereoisomer. Looking at the reactions that take place in this experiment, it is likely that more than one product is formed from the reactions of benzyl and benzoin. The TLC plate for the reduction of benzil
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This note was uploaded on 10/24/2008 for the course CHEM 3BL taught by Professor Chunmei during the Spring '08 term at Berkeley.

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Lab #4 - Sodium Borohydride Reduction - The Sodium...

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