Organic Laboratory Techniques

by Fessenden, Ralph J.; Fessenden, Joan S.

• ISBN13: 9780534201609
• ISBN10: 0534201601
• Format: Paperback
• Copyright: 1993-02-01
• Publisher: Brooks Cole

Summary

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

Preface
Introduction to the Organic Laboratory	p. 1
Safety in the Laboratory	p. 1
The Laboratory Notebook	p. 8
Laboratory Equipment	p. 12
Crystallization	p. 23
Solvents for Crystallization	p. 24
Steps in Crystallization	p. 26
Supplemental Procedures	p. 33
Melting Points	p. 39
Characteristics of Melting Points	p. 39
Melting-Point Apparatus	p. 42
Steps in Determining a Melting Point	p. 43
Supplemental Procedures	p. 45
Extraction	p. 49
Immiscible Liquids	p. 50
Distribution Coefficients	p. 51
Extraction Solvents	p. 53
Chemically Active Extraction	p. 54
Steps in Extraction	p. 58
Additional Techniques Used in Extractions	p. 62
Other Extraction Techniques	p. 66
Drying Organic Solutions	p. 71
Extraction with Aqueous Sodium Chloride	p. 71
Solid Inoranic Drying Agents	p. 71
Procedure for Using Solid Inorganic Drying Agents	p. 72
Azeotropic Drying	p. 73
Simple Distillation	p. 77
Characteristics of Distillation	p. 77
Steps in a Simple Distillation	p. 84
Microscale and Semi-Microscale Distillation	p. 88
Fractional Distillation	p. 93
Efficiency of the Fractionation Column	p. 93
Steps in Fractional Distillation	p. 95
Microscale Fractional Distillation	p. 96
Vacuum Distillation	p. 99
Boiling Point and Pressure	p. 99
Apparatus for Simple Vacuum Distillation	p. 100
Steps in Vacuum Distillation	p. 104
Steam Distillation	p. 107
Characteristics of Steam Distillation	p. 107
Amount of Water Needed in a Steam Distillation	p. 108
Apparatus for Steam Distillation	p. 109
Sublimation	p. 111
Atmospheric Sublimation	p. 112
Vacuum Sublimation	p. 113
Refractive Index	p. 115
Correcting for Temperature Differences	p. 116
Steps in Using a Refractometer	p. 117
Column Chromatography	p. 119
Gravity Column Chromatography	p. 120
Flash Chromatography (Macroscale)	p. 126
Flash Chromatography (Microscale)	p. 128
High-Performance Liquid Chromatography (HPLC)	p. 130
Thin-Layer Chromatography	p. 133
The R[subscript f] Value	p. 133
Equipment for TLC	p. 135
Steps in a TLC Analysis	p. 136
A Related Technique: Paper Chromatography	p. 138
Gas Chromatography	p. 141
Gas Chromatography	p. 141
The Gas Chromatography	p. 143
Steps in a GC Analysis	p. 147
Problems Encountered in GC	p. 148
Uses of Gas Chromatograms	p. 149
Carrying Out Typical Reactions	p. 153
Stirring	p. 153
Heating Reaction Mixtures	p. 154
Controlling Exothermic Reactions	p. 156
Adding Reagents to a Reaction Mixture	p. 157
Excluding Moisture from a Reaction Mixture	p. 158
Setting Up a Three-Neck Reaction Flask	p. 159
Hydrogen Halide Gas Traps	p. 161
Infrared Spectroscopy	p. 163
The Infrared Spectrum	p. 163
Absorption of Infrared Radiation	p. 164
Interpreting Infrared Spectra	p. 164
Identifying Types of Compounds	p. 165
Preparing a Sample for an Infrared Spectrum	p. 173
Instrumentation	p. 176
Proton Nuclear Magnetic Resonance Spectroscopy	p. 179
The NMR Spectrum	p. 179
Interpreting NMR Spectra	p. 181
Use of Deuterium in Proton NMR Spectroscopy	p. 191
NMR Spectra of Unknowns	p. 192
The NMR Spectrometer	p. 192
Preparing Samples for NMR Spectra	p. 193
The Chemical Literature	p. 197
Introduction to the Chemical Literature	p. 197
Secondary Literature	p. 198
Primary Literature	p. 201
Commonly Used Calculations	p. 203
Molarity	p. 203
Normality	p. 204
Dilutions	p. 205
Percent Concentrations	p. 205
Percent Yields and Theoretical Yields	p. 206
Elemental Analyses	p. 209
Determining the Empirical Formula	p. 209
Determining the Molecular Formula	p. 210
Interpreting the Results of Elemental Analysis	p. 211
Degree of Unsaturation	p. 211
Health Hazards of Compounds Used in Organic Chemistry	p. 213
Where to Find Chemical Hazard Information	p. 213
Understanding Health Hazard Warnings	p. 216
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