Organic Laboratory Techniques

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

• ISBN13: 9780534379810
• ISBN10: 0534379818
• Edition: 3rd
• Format: Paperback
• Copyright: 2000-07-12
• Publisher: Cengage Learning

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	1	(1)
Safety in the Laboratory	1	(7)
The Laboratory Notebook	8	(4)
Laboratory Equipment	12	(11)
Crystallization	23	(16)
Solvents for Crystallization	24	(2)
Steps in Crystallization	26	(7)
Supplemental Procedures	33	(6)
Melting Points	39	(10)
Characteristics of Melting Points	39	(3)
Melting-Point Apparatus	42	(1)
Steps in Determining a Melting Point	43	(2)
Supplemental Procedures	45	(4)
Extraction	49	(22)
Immiscible Liquids	50	(1)
Distribution Coefficients	51	(2)
Extraction Solvents	53	(1)
Chemically Active Extraction	54	(4)
Steps in Extraction	58	(4)
Additional Techniques Used in Extractions	62	(4)
Other Extraction Techniques	66	(5)
Drying Organic Solutions	71	(6)
Extraction with Aqueous Sodium Chloride	71	(1)
Solid Inorganic Drying Agents	71	(1)
Procedure for Using Solid Inorganic Drying Agents	72	(1)
Azeotropic Drying	73	(4)
Simple Distillation	77	(16)
Characteristics of Distillation	77	(7)
Steps in a Simple Distillation	84	(4)
Microscale and Semi--Microscale Distillation	88	(5)
Fractional Distillation	93	(6)
Efficiency of the Fractionation Column	93	(2)
Steps in Fractional Distillation	95	(1)
Microscale Fractional Distillation	96	(3)
Vacuum Distillation	99	(8)
Boiling Point and Pressure	99	(1)
Apparatus for Simple Vacuum Distillation	100	(4)
Steps in Vacuum Distillation	104	(3)
Steam Distillation	107	(4)
Characteristics of Steam Distillation	107	(1)
Amount of Water Needed in a Steam Distillation	108	(1)
Apparatus for Steam Distillation	109	(2)
Sublimation	111	(4)
Atmospheric Sublimation	112	(1)
Vacuum Sublimation	113	(2)
Refractive Index	115	(4)
Correcting for Temperature Differences	116	(1)
Steps in Using a Refractometer	117	(2)
Column Chromatography	119	(14)
Gravity Column Chromatography	120	(6)
Flash Chromatography (Macroscale)	126	(2)
Flash Chromatography (Microscale)	128	(2)
High-Performance Liquid Chromatography (HPLC)	130	(3)
Thin-Layer Chromatography	133	(8)
The Rf Value	133	(2)
Equipment for TLC	135	(1)
Steps in a TLC Analysis	136	(2)
A Related Technique: Paper Chromatography	138	(3)
Gas Chromatography	141	(12)
Gas Chromatography	141	(2)
The Gas Chromatograph	143	(4)
Steps in a GC Analysis	147	(1)
Problems Encountered in GC	148	(1)
Uses of Gas Chromatograms	149	(4)
Carrying Out Typical Reactions	153	(10)
Stirring	153	(1)
Heating Reaction Mixtures	154	(2)
Controlling Exothermic Reactions	156	(1)
Adding Reagents to a Reaction Mixture	157	(1)
Excluding Moisture from a Reaction Mixture	158	(1)
Setting Up a Three-Neck Reaction Flask	159	(2)
Hydrogen Halide Gas Traps	161	(2)
Infrared Spectroscopy	163	(16)
The Infrared Spectrum	163	(1)
Absorption of Infrared Radiation	164	(1)
Interpreting Infrared Spectra	164	(1)
Identifying Types of Compounds	165	(8)
Preparing a Sample for an Infrared Spectrum	173	(3)
Instrumentation	176	(3)
Proton Nuclear Magnetic Resonance Spectroscopy	179	(18)
The NMR Spectrum	179	(2)
Interpreting NMR Spectra	181	(10)
Use of Deuterium in Proton NMR Spectroscopy	191	(1)
NMR Spectra of Unknowns	192	(1)
The NMR Spectrometer	192	(1)
Preparing Samples for NMR Spectra	193	(4)
The Chemical Literature	197	(6)
Introduction to the Chemical Literature	197	(1)
Secondary Literature	198	(3)
Primary Literature	201	(2)
Appendix I Commonly Used Calculations	203	(6)
1 Molarity	203	(1)
2 Normality	204	(1)
3 Dilutions	205	(1)
4 Percent Concentrations	205	(1)
5 Percent Yields and Theoretical Yields	206	(3)
Appendix II Elemental Analyses	209	(4)
1 Determining the Empirical Formula	209	(1)
2 Determining the Molecular Formula	210	(1)
3 Interpreting the Results of Elemental Analysis	211	(1)
4 Degree of Unsaturation	211	(2)
Appendix III Health Hazards of Compounds Used in Organic Chemistry	213
1 Where to Find Chemical Hazard Information	213
2 Understanding Health Hazard Warnings	216