Experimental Organic Chemistry

Philippa B. Cranwell, PhD is a Lecturer in the Department of Chemistry, University of Reading, UK. Laurence M. Harwood, PhD is Professor of Organic Chemistry in the Department of Chemistry and Director of the Chemical Analysis Facility, University of Reading, UK. Christopher J. Moody, PhD is Sir Jesse Boot Professor in the School of Chemistry, University of Nottingham, UK.

About 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