Synthetic Organic Chemists Companion

Michael C. Pirrung9780470107072, 0470107073

The Organic Chemists’ Companion provides a practical, hands-on resource for students and practitioners of organic synthesis. It presents the fundamentals and guides the reader through the entire process of organic synthesis. It includes basic instructions on everything from on handling reagents, gases, and solvents to conducting and working up/purifying reactions as well as applying analytical techniques to identify the reaction product.Packed with data and practical tips and organized for quick referenceIncludes guidelines for literature searches to help readers find additional informationFeatures colour photos, drawings, charts, graphs, and tables to complement the informationIncludes real-life examples showing how to apply the information.

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Table of contents :
The Synthetic Organic Chemist’s Companion……Page 4
CONTENTS……Page 8
PREFACE……Page 14
ACKNOWLEDGMENTS……Page 16
1.1 Commercial Availability……Page 18
1.2 Literature Preparations……Page 20
2.1 Short Path Distillation……Page 24
2.2 Ampules……Page 28
2.3 Reagent Solutions……Page 29
2.4 Titration……Page 30
2.5 Reagent Storage……Page 33
2.6 Subtle Reagent Variations……Page 34
2.8 Reagent Properties……Page 35
3.2 Tanks or Cylinders……Page 36
3.3 Gas Safety……Page 39
CHAPTER 4 REACTIONS ON A SMALL SCALE—1 TO 25mmol……Page 40
4.1 Reaction Flasks……Page 41
4.2 Stirring……Page 43
4.3 Glass Joints……Page 46
4.4 Inert Atmosphere……Page 47
4.5 Apparatus for Addition……Page 53
4.6 Condensers……Page 58
4.7 Other Equipment and Considerations……Page 60
5.1 Heating……Page 62
5.2 Cooling……Page 66
6.2 Purity……Page 70
6.3 Degassing……Page 75
6.4 Ammonia……Page 77
CHAPTER 7 THE RESEARCH NOTEBOOK……Page 80
8.2 Azeotropic Drying……Page 86
8.3 Stoichiometry……Page 87
8.4 Syringe and Inert Atmosphere Techniques……Page 91
8.5 General Procedure for Transfer of Materials by Syringe……Page 92
8.6 Addition……Page 94
8.7.1 Water Removal……Page 96
8.7.2 Reactions above Atmospheric Pressure……Page 98
8.7.3 Reagent Gases……Page 100
8.8 Quenching……Page 103
8.9.1 Diazomethane……Page 104
8.9.3 Hydrogen Peroxide……Page 106
8.10 Reaction Time versus Purification Time……Page 108
9.1 Thin Layer Chromatography (TLC)……Page 110
9.1.2 Spotting TLC Plates……Page 111
9.1.3 Eluting TLC Plates……Page 113
9.1.4 Visualizing TLC Plates……Page 115
9.2 Gas Chromatography (GC)……Page 120
9.3 High-Pressure Liquid Chromatography (HPLC)……Page 121
9.4 NMR Spectroscopy……Page 122
CHAPTER 10 WORKING UP REACTIONS……Page 124
10.1 Solvent Extraction……Page 125
10.2 Drying Organic Solutions……Page 129
10.3.4 Reactions Involving Aluminum Reagents……Page 131
10.3.5 Reactions Involving Tin Reagents……Page 132
CHAPTER 11 EVAPORATION……Page 134
12.1 Vacuum Sources……Page 140
12.2 Vacuum Manifolds……Page 141
12.3 Vacuum Gauges……Page 143
13.1 Distillation……Page 148
13.2 Silica Gel Chromatography……Page 149
13.3 Flash Column Chromatography……Page 150
13.5.2 Oxalic Acid-Coated Silica Gel……Page 153
13.5.3 Silver Nitrate-Impregnated Silica Gel……Page 154
13.5.4 Other Sorbents……Page 155
13.6 Preparative Gas Chromatography……Page 156
14.1 Nuclear Magnetic Resonance Spectroscopy (NMR)……Page 158
14.2 Infrared Spectroscopy (IR)……Page 163
14.3 Ultraviolet Spectroscopy (UV)……Page 164
14.4 Combustion Analysis……Page 166
14.5 Mass Spectrometry……Page 167
14.6 Crystallography……Page 168
CHAPTER 15 CLEANING UP AFTER THE REACTION……Page 170
16.2 The Org. Syn. Prep……Page 172
16.3 Comparison……Page 173
CHAPTER 17 STRATEGIES FOR REACTION OPTIMIZATION……Page 174
1 NMR SPECTRAL DATA OF COMMON CONTAMINANTS OF ORGANIC REACTION PRODUCTS……Page 178
2 SYNTHETIC SOLVENT SELECTION CHART……Page 186
3 RECIPES FOR TLC STAINS……Page 188
4 MIXOTROPIC SERIES……Page 190
5 STUCK JOINTS……Page 192
6 ACIDITIES OF ORGANIC FUNCTIONAL GROUPS……Page 194
7 ACIDITIES OF ORGANIC FUNCTIONAL GROUPS IN DMSO……Page 198
8 WEB RESOURCES FOR SYNTHETIC CHEMISTRY……Page 202
BIBLIOGRAPHY……Page 204
INDEX……Page 206