Techniques in Organic Chemistry

by Mohrig, Jerry R.; Hammond, Christina Noring; Schatz, Paul F.

• ISBN13: 9780716769354
• ISBN10: 0716769352
• Edition: 2nd
• Format: Paperback
• Copyright: 2006-01-01
• Publisher: W. H. Freeman

Summary

"Techniques in Organic Chemistry" is the most comprehensive and detailed presentation of lab techniques available for organic chemistry students--and the least expensive. It combines specific instructions for 3 different kinds of laboratory glassware (miniscale, standard-taper microscale, )Williamson microscale) and offers extensive coverage of spectroscopic techniques, and a strong emphasis on safety issues. The techniques manual can be packaged with either version of Mohrig, "Modern Projects and Experiments in Organic Chemistry, " with an instructor's own experiments through Freeman Custom Publishing, or may be purchased separately.

Table of Contents

PART 1 BASIC TECHNIQUES	1	(174)
1 Safety in the Laboratory and Protecting the Environment	2	(20)
Safety in The Laboratory	2	(14)
1.1 Causes of Laboratory Accidents	2	(3)
1.2 Safety Features in the Laboratory	5	(1)
1.3 Preventing Accidents	6	(2)
1.4 What to Do If an Accident Occurs	8	(2)
1.5 Chemical Toxicology	10	(2)
1.6 Where to Find Chemical Safety Information	12	(4)
Protecting the Environment	16	(6)
1.7 Green Chemistry	16	(1)
1.8 How Can a Laboratory Procedure Be Made Green?	17	(3)
1.9 Atom Economy and Reaction Efficiency	20	(2)
2 Laboratory Glassware	22	(8)
2.1 Desk Equipment	23	(1)
2.2 Standard Taper Miniscale Glassware	23	(3)
2.3 Microscale Glassware	26	(2)
2.4 Cleaning and Drying Laboratory Glassware	28	(2)
3 The Laboratory Notebook	30	(4)
3.1 Organization of the Laboratory Notebook	30	(3)
3.2 Calculation of the Percent Yield	33	(1)
4 Using Handbooks and Online Databases	34	(4)
4.1 Handbooks	34	(4)
4.2 Online Resources	38	(1)
5 Measuring Mass and Volume	38	(9)
5.1 Weighing	38	(3)
5.2 Measuring Volume	41	(6)
6 Heating and Cooling Methods	47	(9)
6.1 Boiling Stones	47	(1)
6.2 Heating Devices	48	(6)
6.3 Cooling Methods	54	(1)
6.4 Laboratory Jacks	55	(1)
7 Assembly of Reaction Apparatus and Planning a Chemical Reaction	56	(19)
Assembly of Reaction Apparatus	56	(14)
7.1 Refluxing a Reaction Mixture	56	(2)
7.2 Addition of Reagents During a Reaction	58	(2)
7.3 Anhydrous and Inert Atmosphere Reaction Conditions	60	(7)
7.3a ANHYDROUS REACTION CONDITIONS	60	(2)
7.3b INERT ATMOSPHERE REACTION CONDITIONS	62	(5)
7.4 Removal of Noxious Vapors	67	(3)
Planning a Chemical Reaction	70	(5)
7.5 Library Work	71	(1)
7.6 Modifying the Scale of a Reaction and Carrying It Out	71	(4)
8 Extraction and Drying Organic Liquids	75	(25)
Extraction	75	(18)
8.1 Understanding How Extraction Works	77	(3)
8.2 Miniscale Extractions	80	(2)
8.3 Additional Information About Extractions	82	(2)
8.4 Summary of Miniscale Extraction Procedure	84	(1)
8.5 Using Pasteur Pipets to Transfer Liquids in Microscale Operations	85	(1)
8.6 Microscale Extractions	86	(6)
8.6a EQUIPMENT AND TECHNIQUES COMMON TO ALL MICROSCALE EXTRACTIONS	87	(2)
8.6b MICROSCALE EXTRACTIONS WITH AN ORGANIC PHASE DENSER THAN WATER	89	(1)
8.6c MICROSCALE EXTRACTIONS WITH AN ORGANIC PHASE LESS DENSE THAN WATER	90	(2)
8.7 Sources of Confusion in Extractions	92	(1)
Drying Organic Liquids and Recovering the Product	93	(7)
8.8 Drying Agents	93	(2)
8.9 Methods for Separating Drying Agents from Organic Liquids	95	(1)
8.10 Recovery of the Organic Product from the Dried Extraction Solution	96	(3)
8.11 Sources of Confusion in Drying Liquids	99	(1)
9 Recrystallization	100	(16)
9.1 Theory of Recrystallization	100	(1)
9.2 Choice of Recrystallization Solvent	101	(2)
9.3 How to Select a Proper Recrystallization Solvent	103	(1)
9.4 Planning and Carrying Out Successful Recrystallizations	104	(2)
9.5 Miniscale Procedure for Recrystallizing a Solid	106	(4)
9.6 Summary of the Miniscale Recrystallization Procedure	110	(1)
9.7 Microscale Recrystallization Methods	111	(3)
9.7a RECRYSTALLIZING LESS THAN 300 MILLIGRAMS OF A SOLID	111	(1)
9.7b RECRYSTALLIZING UP TO 150 MILLIGRAMS OF A SOLID IN A CRAIG TUBE	112	(2)
9.8 Summary of Microscale Recrystallization Procedures	114	(1)
9.9 Sources of Confusion	114	(2)
10 Melting Points and Melting Ranges	116	(1)
10.1 Melting Point Theory	117	(2)
10.2 Apparatus for Determining Melting Ranges	119	(2)
10.3 Determining Melting Ranges	121	(2)
10.4 Mixture Melting Point	123	(1)
10.5 Thermometer Calibration	124	(1)
10.6 Summary of Mel-Temp Melting-Point Determinations	125	(1)
10.7 Sources of Confusion	125	(2)
11 Boiling Points and Distillation	127	(1)
11.1 Determination of Boiling Points	128	(2)
11.2 Distillation and Separation of Mixtures	130	(3)
11.3 Simple Distillation	133	(9)
11.3a MINISCALE SHORT-PATH DISTILLATION	137	(1)
11.3b MICROSCALE DISTILLATION USING STANDARD-TAPER APPARATUS	138	(2)
11.3c MICROSCALE DISTILIATION USING WILLIAMSON APPARATUS	140	(2)
11.4 Fractional Distillation	142	(4)
11.5 Azeotropic Distillation	146	(1)
11.6 Vacuum Distillation	147	(6)
11.7 Steam Distillation	153	(3)
11.8 Sources of Confusion	156	(2)
12 Sublimation	158	(1)
12.1 Assembling the Apparatus for a Sublimation	158	(2)
12.2 Carrying Out a Sublimation	160	(1)
13 Refractometry	161	(1)
13.1 Theory of Refractometry	161	(1)
13.2 The Refractometer	162	(1)
13.3 Steps in Determining a Refractive Index	163	(1)
13.4 Temperature Correction	164	(1)
14 Optical Activity and Enantiomeric Analysis	165	(1)
14.1 Mixtures of Optical Isomers: Separation/Resolution	165	(3)
14.2 Polarimetry	168	(2)
14.3 Using Polarimeter Tubes	170	(1)
14.4 Specific Rotation	171	(1)
14.5 Enantiomeric Excess (Optical Purity)	172	(1)
14.6 Modern Methods of Enantiomeric Analysis	172	(3)
PART 2 CHROMATOGRAPHY	175	(1)
15 Thin-Layer Chromatography	177	(50)
15.1 Introduction to Thin-Layer Chromatography (TLC)	177	(2)
15.2 Plates for Thin-Layer Chromatography	179	(2)
15.3 Sample Application	181	(2)
15.4 Development of a TLC Plate	183	(1)
15.5 Visualization Techniques	184	(2)
15.6 Summary of TLC Procedure	186	(1)
15.7 How to Choose a Developing Solvent When None Is Specified	186	(2)
15.8 Sources of Confusion	188	(2)
16 Gas-liquid Chromatography	190	(1)
16.1 Instrumentation for CC	191	(1)
16.2 Types of Columns and Liquid Stationary Phases	192	(2)
16.3 Detectors	194	(2)
16.4 Recorders	196	(1)
16.5 Practical GC Operating Procedures	197	(3)
16.6 Sources of Confusion	200	(2)
16.7 Identification of Components Shown on a Chromatogram	202	(1)
16.8 Quantitative Analysis	203	(3)
17 Liquid Chromatography	206	(1)
17.1 Adsorbents	207	(1)
17.2 Elution Solvents	208	(2)
17.3 Amount of Adsorbent and Column Dimensions	210	(2)
17.4 Preparation of a Chromatography Column	212	(4)
17.4a PREPARATION OF A MINISCALE COLUMN	212	(1)
17.4b PREPARATION OF A WILLIAMSON MICROSCALE COLUMN	213	(1)
17.4c PREPARATION AND ELUTION OF A MICROSCALE COLUMN	214	(2)
17.5 Sample Application and Elution Techniques	216	(3)
17.6 Summary of Column Chromatography Procedure	219	(1)
17.7 Flash Chromatography	219	(2)
17.8 Sources of Confusion	221	(2)
17.9 High-Performance Liquid Chromatography	223	(4)
PART 3 SPECTROSCOPIC METHODS	227	(1)
18 Infrared Spectroscopy	228
18.1 IR Spectra	228	(1)
18.2 Molecular Vibrations	228	(5)
18.3 IR Instrumentation	233	(2)
18.4 Operating an FTIR Spectrometer	235	(1)
18.5 Techniques of Sample Preparation	236	(7)
18.6 Interpreting IR Spectra	243	(13)
18.7 A Procedure for Interpreting an IR Spectrum	256	(2)
18.8 A Case Study	258	(1)
18.9 Sources of Confusion	259	(8)
19 Nuclear Magnetic Resonance Spectroscopy	267	(2)
NMR Instrumentation and Sample Preparation	269	(7)
19.1 NMR Instrumentation	269	(2)
19.2 Preparing Samples for NMR Analysis	271	(5)
19.3 Summary of Steps for Preparing an NMR Sample	276	(1)
Interpreting ¹H NMR Spectra	276	(45)
19.4 NMR Information	276	(1)
19.5 How Many Types of Protons Are Present?	276	(1)
19.6 Counting Protons (Integration)	277	(1)
19.7 Chemical Shift	278	(6)
19.8 Quantitative Estimation of Chemical Shifts	284	(10)
19.9 Spin-Spin Coupling (Splitting)	294	(10)
19.10 Sources of Confusion	304	(7)
19.11 Two Case Studies	311	(7)
19.12 Advanced Topics in ¹H-NMR	318	(3)
¹³C and Two-Dimensional NMR	321
19.13 ¹³C NMR	321	(8)
19.14 Determining Numbers of Protons on Carbon Atoms	329	(2)
19.15 Two-Dimensional Correlated Correlated Spectroscopy (2D COSY)	331	(10)
20 Mass Spectrometry	341
20.1 Mass Spectrometers	312	(34)
20.2 Mass Spectra and the Molecular Ion	346	(3)
20.3 High-Resolution Mass Spectrometry	349	(2)
20.4 Mass Spectral Libraries	351	(2)
20.5 Fragmentation of the Molecule	353	(5)
20.6 A Case Study	358	(2)
20.7 Sources of Confusion	360
Appendix A Computational Chemistry	AP-1
Appendix B The literature of Organic Chemistry	AP-12
Appendix C Integrated Spectroscopy Problems	AP-18
Index	I-1