Organic Laboratory Techniques

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  • Format: Paperback
  • Copyright: 1993-02-01
  • Publisher: Brooks Cole
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Supplemental Materials

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  • The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any access cards, study guides, lab manuals, CDs, etc.


This highly effective and practical manual is designed to be used as a supplementary text for the organic chemistry laboratory course - and with virtually any main text - in which experiments are supplied by the instructor or in which the students work independently. Each technique contains a brief theoretical discussion. Steps used in each technique, along with common problems that might arise. These respected and renowned authors include supplemental or related procedures, suggested experiments, and suggested readings for many of the techniques. Additionally, each chapter ends with a set of study problems that primarily stress the practical aspects of each technique, and microscale techniques are included throughout the text, as appropriate. Additional exercises, reference material, and quizzes are available online.

Table of Contents

Introduction to the Organic Laboratoryp. 1
Safety in the Laboratoryp. 1
The Laboratory Notebookp. 8
Laboratory Equipmentp. 12
Crystallizationp. 23
Solvents for Crystallizationp. 24
Steps in Crystallizationp. 26
Supplemental Proceduresp. 33
Melting Pointsp. 39
Characteristics of Melting Pointsp. 39
Melting-Point Apparatusp. 42
Steps in Determining a Melting Pointp. 43
Supplemental Proceduresp. 45
Extractionp. 49
Immiscible Liquidsp. 50
Distribution Coefficientsp. 51
Extraction Solventsp. 53
Chemically Active Extractionp. 54
Steps in Extractionp. 58
Additional Techniques Used in Extractionsp. 62
Other Extraction Techniquesp. 66
Drying Organic Solutionsp. 71
Extraction with Aqueous Sodium Chloridep. 71
Solid Inoranic Drying Agentsp. 71
Procedure for Using Solid Inorganic Drying Agentsp. 72
Azeotropic Dryingp. 73
Simple Distillationp. 77
Characteristics of Distillationp. 77
Steps in a Simple Distillationp. 84
Microscale and Semi-Microscale Distillationp. 88
Fractional Distillationp. 93
Efficiency of the Fractionation Columnp. 93
Steps in Fractional Distillationp. 95
Microscale Fractional Distillationp. 96
Vacuum Distillationp. 99
Boiling Point and Pressurep. 99
Apparatus for Simple Vacuum Distillationp. 100
Steps in Vacuum Distillationp. 104
Steam Distillationp. 107
Characteristics of Steam Distillationp. 107
Amount of Water Needed in a Steam Distillationp. 108
Apparatus for Steam Distillationp. 109
Sublimationp. 111
Atmospheric Sublimationp. 112
Vacuum Sublimationp. 113
Refractive Indexp. 115
Correcting for Temperature Differencesp. 116
Steps in Using a Refractometerp. 117
Column Chromatographyp. 119
Gravity Column Chromatographyp. 120
Flash Chromatography (Macroscale)p. 126
Flash Chromatography (Microscale)p. 128
High-Performance Liquid Chromatography (HPLC)p. 130
Thin-Layer Chromatographyp. 133
The R[subscript f] Valuep. 133
Equipment for TLCp. 135
Steps in a TLC Analysisp. 136
A Related Technique: Paper Chromatographyp. 138
Gas Chromatographyp. 141
Gas Chromatographyp. 141
The Gas Chromatographyp. 143
Steps in a GC Analysisp. 147
Problems Encountered in GCp. 148
Uses of Gas Chromatogramsp. 149
Carrying Out Typical Reactionsp. 153
Stirringp. 153
Heating Reaction Mixturesp. 154
Controlling Exothermic Reactionsp. 156
Adding Reagents to a Reaction Mixturep. 157
Excluding Moisture from a Reaction Mixturep. 158
Setting Up a Three-Neck Reaction Flaskp. 159
Hydrogen Halide Gas Trapsp. 161
Infrared Spectroscopyp. 163
The Infrared Spectrump. 163
Absorption of Infrared Radiationp. 164
Interpreting Infrared Spectrap. 164
Identifying Types of Compoundsp. 165
Preparing a Sample for an Infrared Spectrump. 173
Instrumentationp. 176
Proton Nuclear Magnetic Resonance Spectroscopyp. 179
The NMR Spectrump. 179
Interpreting NMR Spectrap. 181
Use of Deuterium in Proton NMR Spectroscopyp. 191
NMR Spectra of Unknownsp. 192
The NMR Spectrometerp. 192
Preparing Samples for NMR Spectrap. 193
The Chemical Literaturep. 197
Introduction to the Chemical Literaturep. 197
Secondary Literaturep. 198
Primary Literaturep. 201
Commonly Used Calculationsp. 203
Molarityp. 203
Normalityp. 204
Dilutionsp. 205
Percent Concentrationsp. 205
Percent Yields and Theoretical Yieldsp. 206
Elemental Analysesp. 209
Determining the Empirical Formulap. 209
Determining the Molecular Formulap. 210
Interpreting the Results of Elemental Analysisp. 211
Degree of Unsaturationp. 211
Health Hazards of Compounds Used in Organic Chemistryp. 213
Where to Find Chemical Hazard Informationp. 213
Understanding Health Hazard Warningsp. 216
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