Description
Book SynopsisThe definitive guide to the principles and practice of experimental organic chemistry - fully updated and now featuring more than 100 experiments The latest edition of this popular guide to experimental organic chemistry takes students from their first day in the laboratory right through to complex research procedures.
Table of ContentsAbout the authors ix
Preface to the third edition xi
About the companion website xv
PART 1: LABORATORY PRACTICE 1
1 Safety in the chemical laboratory 3
1.1 Essential rules for laboratory safety 4
1.2 Hazardous chemicals 7
1.3 Disposal of hazardous waste 11
1.4 Accident procedures 12
2 Glassware and equipment in the laboratory 15
2.1 Glass equipment 16
2.2 Hardware 21
2.3 Heating 24
2.4 Stirring 30
2.5 Vacuum pumps 32
2.6 The rotary evaporator 42
2.7 Catalytic hydrogenation 46
2.8 Ozonolysis 48
2.9 Irradiation 50
2.10 Compressed gases 54
3 Organic reactions: From starting materials to pure organic product 61
3.1 Handling chemicals 62
3.2 The reaction 81
3.3 Purification of organic compounds 105
4 Qualitative analysis of organic compounds 185
4.1 Purity 185
4.2 Determination of structure using chemical methods 202
5 Spectroscopic analysis of organic compounds 207
5.1 Absorption spectroscopy 207
5.2 Infrared spectroscopy 209
5.3 Nuclear magnetic resonance spectroscopy 227
5.4 Ultraviolet spectroscopy 279
5.5 Mass spectrometry 295
6 Keeping records: The laboratory notebook and chemical literature 311
6.1 The laboratory notebook 312
6.2 The research report 322
6.3 The chemical literature 327
PART 2: EXPERIMENTAL PROCEDURES 329
Introduction 331
List of experiments 333
Experiments that can be taken in sequence 353
Experiments that can be used to compare directly different techniques for undertaking a reaction 354
Experiments that illustrate particular techniques 354
7 Functional group interconversions 355
7.1 Simple transformations 355
7.2 Reactions of alkenes 366
7.3 Substitution 386
7.4 Reduction 390
7.5 Oxidation 424
7.6 Rearrangements 436
8 Carbon–carbon bond]forming reactions 443
8.1 Grignard and organolithium reagents 444
8.2 Enolate anions 456
8.3 Heteroatom]stabilized carbanions 484
8.4 Aromatic electrophilic substitution 504
8.5 Pericyclic reactions 514
8.6 Metal]mediated coupling reactions 534
9 Experiments using enabling technologies 545
9.1 Microwave chemistry 545
9.2 Flow chemistry 554
10 Projects 569
10.1 Natural product isolation and identification 569
10.2 Project in organic synthesis 578
10.3 Aspects of physical organic chemistry 608
APPENDICES 627
Organic solvents 629
Spectroscopic correlation tables 635
Index of chemicals 649
General index 657
