Organic Lab Reactions 183

Organic Lab Reactions 183 - SELECTION OF EXPERIMENTAL...

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CHAPTER 5 REDUCTION WITH ALUMINUM ALKOXIDES (The Meerwein-Ponndorf-Verley Reduction) A. L. WILDS University of Wisconsin CONTENTS PAGE INTRODUCTION . . 179 The Nature of the Reaction 180 Advantages of Aluminum Isopropoxide over Other Alkoxides 181 THE SCOPE OF THE REACTION 18? Selective Reduction of Carbonyl Groups 183 Stereochemical Configuration of the Reduction Products 185 Limitations of the Method 186 Side Reactions 187 Condensation 187 Dehydration of the Alcohol 188 Migration of Double Bonds 189 Ether Formation 190 Further Reduction to a Hydrocarbon '. 191 Reduction of Keto Esters 191 Reduction of Esters of Hydroxy Ketones 192 Reduction of a-Bromoketones 193
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Unformatted text preview: SELECTION OF EXPERIMENTAL CONDITIONS 194 Solvent and Temperature . . 194 Preparation and Amount of Aluminum Isopropoxide 195 Apparatus 196 Recovery of the Isopropyl Alcohol 197 EXPERIMENTAL PROCEDURES . . . . ^. . . . 198 Aluminum Isopropoxide 198 Acetone Test Reagent (2,4-Dinitrophenylhydrazine) 200 Reduction of Aldehydes 200 Procedure I (For Volatile Aliphatic Aldehydes and Ketones) 200 Reduction of Crotonaldehyde 200 Procedure II (For Aromatic Aldehydes) 201 Reduction of Benzaldehyde with 0.5 Equivalent of Aluminum Isopropox-ide. Use of the Hahn Condenser 201 Procedure III. The Use of Aluminum Ethoxide 202 178...
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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