Preface ix
About the Companion Website xi
<b>Chapter 1 Introduction 1</b>
1.1 Systematic Identification of Organic Compounds: The Need for Organic Qualitative Analysis 1
1.2 Suggestions to Students and Instructors 3
<b>Chapter 2 Laboratory Safety 7</b>
2.1 Working Safely in the Laboratory 7
2.2 Training 10
2.3 Personal Protection Equipment 10
2.4 Safety Data Sheets 11
2.5 Storage of Chemicals 12
2.6 Disposal of Chemicals 13
2.7 Safely Using Equipment in the Laboratory 13
<b>Chapter 3 Identification of Unknowns 15</b>
3.1 Discussion of Report Form 15
3.2 Preliminary Examination 22
3.3 Physical Properties 22
3.4 Molecular Weight Determination 22
3.5 Molecular Formula Determination 23
3.6 Solubility Tests 23
3.7 Infrared, Nuclear Magnetic Resonance, and Mass Spectra Analyses 24
3.8 Classification Tests 24
3.9 Preparation of a Satisfactory Derivative 25
3.10 Mixtures 26
3.11 Report Forms 26
<b>Chapter 4 Preliminary Examination, Physical Properties, and Elemental Analysis 31</b>
4.1 Preliminary Examination 32
4.2 Determination of Physical Properties 34
4.3 Optical Rotation 53
4.4 Recrystallization 58
4.5 Qualitative Elemental Analysis 61
4.6 Quantitative Elemental Analysis 69
<b>Chapter 5 Classification of Organic Compounds by Solubility 75</b>
5.1 Solubility in Water, Aqueous Acids and Bases, and Ether 76
5.2 Solubility in Organic Solvents 95
<b>Chapter 6 Separation of Mixtures 99</b>
6.1 Preliminary Examinations of Mixtures 100
6.2 Distillation and Sublimation 101
6.3 Extractions: Separations Based Upon
6.4 Chromatography 119
<b>Chapter 7 Nuclear Magnetic Resonance Spectrometry 145</b>
7.1 Theory of Nuclear Magnetic Resonance 145
7.2 Preparation of the Sample 149
7.3 Proton Spectra 151
7.4 13C Spectra 165
7.5 DEPT 179
7.6 COSY 188
7.7 HSQC 190
<b>Chapter 8 Infrared Spectrometry 227</b>
8.1 Theory of Infrared Spectrometry 227
8.2 Preparation of the Sample 230
8.3 Functional Group Identification 234
<b>Chapter 9 Mass Spectrometry 269</b>
9.1 Theory of Mass Spectrometry 269
9.2 Cleavage Reactions 271
<b>Chapter 10 Chemical Tests for Functional Groups 293</b>
10.1 Acid Anhydrides 296
10.2 Acyl Halides 306
10.3 Alcohols 307
10.4 Aldehydes 323
10.5 Amides 332
10.6 Amines and Amine Salts 334
10.7 Amino Acids 349
10.8 Carbohydrates 351
10.9 Carboxylic Acids 359
10.10 Esters 360
10.11 Ethers 361
10.12 Halides 365
10.13 Hydrocarbons--Alkanes 371
10.14 Hydrocarbons--Alkenes 371
10.15 Hydrocarbons--Alkynes 378
10.16 Hydrocarbons--Aromatic 379
10.17 Ketones 384
10.18 Nitriles 386
10.19 Nitro Compounds 386
10.20 Phenols 389
10.21 Sulfonamides, Sulfonic Acids, Sulfonyl Chlorides 393
<b>Chapter 11 The Preparation of Derivatives 397</b>
11.1 Carboxylic Acids, Acid Anhydrides, Acid Halides 397
11.2 Alcohols 409
11.3 Aldehydes And Ketones 414
11.4 Amides 420
11.5 Amines 424
11.6 Amino Acids 432
11.7 Carbohydrates 437
11.8 Esters 440
11.9 Ethers--Aliphatic 450
11.10 Ethers--Aromatic 451
11.11 Halides--Alkyl 454
11.12 Halides--Aromatic 457
11.13 Hydrocarbons--Aromatic 460
11.14 Nitriles 462
11.15 Nitro Compounds 467
11.16 Phenols 468
11.17 Sulfonic Acids, Sulfonyl Chlorides, Sulfonamides 472
<b>Chapter 12 Chemical Literature 479</b>
12.1 Handbooks 480
12.2 Compendia 480
12.3 Spectral Collections 481
12.4 Journals 482
12.5 Abstracts and Indexes 483
12.6 Monographs 486
Appendix I Handy Tables for the Organic Laboratory 487
APPENDIX II Table of Derivatives 493
Appendix III Equipment and Chemicals for the Laboratory 677
Index 685
