Techniques in Organic Chemistry : Miniscale, Standard-Taper Microscale, Williamson Microscale

by Mohrig; Hammond; Schatz

• ISBN13: 9780716766384
• ISBN10: 0716766388
• Edition: 1st
• Format: Paperback
• Copyright: 2002-07-19
• Publisher: W. H. Freeman

Table of Contents

Preface	ix
PART 1 BASIC TECHNIQUES	1	(150)
Safety	2	(14)
Causes of Laboratory Accidents	2	(3)
Safety Features in Your Laboratory	5	(1)
Preventing Accidents	6	(2)
What to Do If an Accident Occurs	8	(1)
Chemical Toxicology	9	(2)
Where to Find Chemical Safety Information	11	(3)
Protecting the Environment	14	(2)
Laboratory Glassware	16	(7)
Desk Equipment	17	(1)
Standard Taper Miniscale Glassware	18	(2)
Microscale Glassware	20	(2)
Cleaning Laboratory Glassware	22	(1)
The Laboratory Notebook	23	(4)
Organization of the Laboratory Notebook	23	(3)
Calculation of the Percent Yield	26	(1)
Using Handbooks and Online Databases	27	(5)
Handbooks	27	(2)
Online Resources	29	(3)
Measuring Mass and Volume	32	(8)
Weighing	32	(2)
Measuring Volume	34	(6)
Heating and Cooling Methods	40	(8)
Boiling Stones	41	(1)
Heating Devices	41	(6)
Cooling Methods	47	(1)
Assembly of Reaction Apparatus	48	(8)
Refluxing a Reaction Mixture	48	(2)
Anhydrous Reaction Conditions	50	(1)
Addition of Reagents During a Reaction	51	(1)
Removal of Noxious Vapors	52	(4)
Extraction and Drying Agents	56	(22)
Extraction: The Theory	58	(1)
Miniscale Extractions	59	(2)
Additional Information About Extractions	61	(3)
Summary of the Miniscale Extraction Procedure	64	(1)
Using Pasteur Pipets to Transfer Liquids in Microscale Operations	65	(2)
Microscale Extractions	67	(5)
Equipment and Techniques Common to All Microscale Extractions	67	(2)
Extractions with an Organic Phase More Dense Than Water	69	(1)
Extractions with an Organic Phase Less Dense Than Water	70	(2)
Drying Organic Liquids	72	(2)
Methods for Separating Drying Agents and Organic Liquids	74	(2)
Recovery of the Organic Product from the Dried Extraction Solution	76	(2)
Recrystallization	78	(15)
Theory of Recrystallization	78	(3)
Selecting a Proper Recrystallization Solvent	81	(1)
What to Do If No Crystals Appear in the Cooled Solution	82	(1)
Pointers for Successful Recrystallizations	83	(1)
Miniscale Procedure for Recrystallizing a Solid	83	(5)
Removing Impurities from the Recrystallization Solution	86	(2)
Summary of the Miniscale Recrystallization Procedure	88	(1)
Microscale Recrystallization Methods	88	(4)
Recrystallizing 300 Milligrams or Less of a Solid	89	(1)
Recrystallizing up to 150 Milligrams of a Solid in a Craig Tube	90	(2)
Summary of the Microscale Recrystallization Procedures	92	(1)
Melting Points and Melting Ranges	93	(11)
Melting Point Theory	93	(3)
Apparatus for Determining Melting Ranges	96	(2)
Determining Melting Ranges	98	(3)
Mixture Melting Point	101	(1)
Thermometer Calibration	102	(1)
Summary of Melting-Point Determination	103	(1)
Boiling Points and Distillation	104	(29)
Determination of Boiling Points	104	(2)
Boiling Points and Separation of Mixtures	106	(3)
Simple Distillation	109	(9)
Miniscale Short-Path Distillation	113	(1)
Microscale Distillation Using Standard Taper Apparatus	113	(3)
Microscale Distillation Using Williamson Apparatus	116	(2)
Fractional Distillation	118	(4)
Azeotropic Distillation	122	(1)
Vacuum Distillation	123	(6)
Steam Distillation	129	(4)
Sublimation	133	(3)
Assembling the Apparatus for a Sublimation	133	(2)
Carrying Out a Sublimation	135	(1)
Refractometry	136	(4)
Theory of Refractometry	13.1	(137)
The Refractometer	137	(1)
Steps in Determining a Refractive Index	138	(1)
Temperature Correction	139	(1)
Optical Activity and Polarimetry	140	(11)
Mixtures of Optical Isomers: Separation/Resolution	140	(3)
Polarimetric Instrumentation	143	(2)
Specific Rotation	145	(1)
Using the Polarimeter	146	(1)
Enantiomeric Excess (Optical Purity)	147	(1)
Chiral Shift Reagents and Chiral Chromatography	147	(4)
PART 2 CHROMATOGRAPHY	151	(44)
Thin-Layer Chromatography	153	(10)
Principles of Thin-Layer Chromatography	153	(2)
Plates for Thin-Layer Chromatography	155	(1)
Sample Application	156	(2)
Development of a TLC Plate	158	(1)
Choice of Developing Solvent	159	(1)
Visualization Techniques	160	(2)
Summary of TLC Procedure	162	(1)
Gas-Liquid Chromatography	163	(15)
Instrumentation	164	(2)
Columns and Liquid Stationary Phases	166	(3)
Detectors	169	(1)
Interpreting Chromatograms	170	(2)
Practical GC Operating Procedures	172	(2)
Identification of Components Shown on a Chromatogram	174	(1)
Quantitative Analysis	175	(3)
Liquid Chromatography	178	(17)
Adsorbents	179	(2)
Elution Solvents	181	(1)
Column Dimensions	182	(2)
Preparing a Miniscale Column	184	(1)
Elution Techniques	185	(2)
Microscale Column Chromatography	187	(2)
Summary of Column Chromatography Procedure	189	(1)
Flash Chromatography	189	(2)
High-Performance Liquid Chromatography	191	(4)
PART 3 SPECTROSCOPIC METHODS	195	(105)
Infrared Spectroscopy	197	(27)
Theory of Molecular Vibration	197	(1)
IR Spectrum	198	(3)
IR Instrumentation	201	(1)
Techniques of Sample Preparation	202	(4)
Interpreting IR Spectra	206	(11)
Sources of Confusion	217	(7)
Nuclear Magnetic Resonance Spectroscopy	224	(60)
NMR Instrumentation	225	(3)
Preparing Samples for NMR Analysis	228	(4)
Summary of Steps for Preparing an NMR Sample	232	(1)
Interpreting NMR Spectra	232	(1)
How Many Types of Hydrogens Are Present?	232	(1)
Counting Hydrogens (Integration)	233	(1)
Chemical Shift	234	(9)
Spin-Spin Splitting (Coupling)	243	(9)
Sources of Confusion	252	(10)
Interpreting 1H NMR Spectra	262	(8)
13C NMR	270	(6)
DEPT Experiments	276	(8)
Mass Spectrometry	284	(16)
Mass Spectrometer	284	(2)
The Molecular Ion	286	(3)
High-Resolution Mass Spectrometry	289	(1)
Fragmentation of the Molecule	290	(6)
Case Study	296	(2)
Sources of Confusion	298	(2)
Integrated Spectroscopy Problems	300
Appendix The Literature of Organic Chemistry	1	(1)
Index	1