CHEM 237 Lab Fall 2009 Objective The purpose of this experiment is to learn a reduction reaction of carbonyl compounds with metal hydride reagents by synthesizing vanillyl alcohol from reaction of vanillin with sodium borohydride (NaBH 4 ). 5 Reagents Vanillin NaBH 4 Deionized (DI) water 10 Theory Reduction of aldehydes and ketones using metal hydride reagents is a synthetic method to various substituted alcohols (Scheme 1). NaBH 4 and LiAlH 4 are the two most common metal hydride reagents used in the reduction of the carbonyl compounds. The reducing agent serves as a nucelophile in the reaction as it contains a source of the nucleophilic hydride (H : 15 -). Na + sodium borohydride Scheme 1. Reduction of aldehydes and ketones with metal hydride reagents C O R R' C O R H or aldehyde ketone reducing agents (NaBH 4 or LiAlH 4 ) C R H or 1 o alcohol 2 o alcohol C R R' HO HO H H B H H H H Li + lithium aluminum hydride Al H H H H In this experiment, vanillin will be reduced to vanillyl 20 alcohol by NaBH
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This note was uploaded on 03/03/2010 for the course CHEM 237 taught by Professor Chong during the Fall '10 term at Illinois Tech.