Lab 10 - Experiment#10 Borohydride Reduction of Vanillin to...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

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.

Ask a homework question - tutors are online