Experimental Organic Chemistry (eBook)

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