Lab #2 Sodium Borohydride Reduction

Lab #2 Sodium Borohydride Reduction - Atif Saleem, ID #...

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Atif Saleem, ID # 19546129, 02-09-2009, Section 101, GSI: Jason Hudak Chemistry 3BL Lab # 2: The Sodium Borohydride Reduction of Benzil and Benzoin Introduction: The purpose of the sodium borohydride reduction lab is to use a reagent which is efficient in terms of cost, and reaction times to reduce ketones at room temperature. Benzil and benzoin are the two ketones to be reduced, and sodium borohydride is the reducing agent. Upon mixing these reagents in 2- propanol, a Thin Layer Chromatography is taken of both products as well as a recrystallization. The crystals are weighed for their actual percent yield, and their melting temperatures are taken. Discussion: Reduction is a type of redox reaction that removes electronegative atoms or adds hydrogen to a molecule. Sodium borohydride produces hydride ions which are considered to be the “nucleophiles” of the reduction. They attack the “electrophile,” or the polarized carbon atom on the ketone in order to reduce it to a hydroxide group. The following sodium borohydride mechanism can be found on page 299 of Vollhardt and Schore’s Organic Chemistry fifth edition: Benzil is first mixed with 2-propanol to yield a yellow, coarse liquid with a strong aroma. Sixteen
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This note was uploaded on 02/04/2010 for the course CHEM 3BL taught by Professor Chunmei during the Spring '08 term at University of California, Berkeley.

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Lab #2 Sodium Borohydride Reduction - Atif Saleem, ID #...

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