Organic Lab Reactions 186

Organic Lab Reactions 186 - ADVANTAGES OF ALUMINUM...

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ADVANTAGES OF ALUMINUM ISOPROPOXIDE 181 peratures eerie oxide 7 or sodium acetate * will accelerate the reaction. In the presence of the aluminum alkoxide the reaction occurs readily at temperatures of 20 to 80°, and as a result many undesirable side reac- tions are avoided. The reaction between an aluminum alkoxide and a ketone can be reversed. This is the basis of the Oppenauer oxidation of a secondary alcohol to the ketone. 46 ' 8 The aluminum derivative of the alcohol is prepared by means of aluminum t-butoxide and is oxidized with a large excess of acetone or cyclohexanone. A polarographic study by Adkins and co-workers '• 10 of the position of the equilibrium between various ketones and a single alcohol demon- strated the true equilibrium nature of the reaction; from the concen- trations of ketones and alcohols at equilibriuin the determination of the relative oxidation-reduction potentials of a number of ketone-alcohol systems was made possible. 10
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