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Inspiring and motivating students from the moment it published, Organic Chemistry has established itself in just one edition as the students' choice of organic chemistry text. This second edition takes all that has made Organic Chemistry the book of choice, and has refined and refocused it to produce a text that is even more student-friendly, more coherent and more logical in its presentation than before. At heart, the second edition remains true to the first, being built on three principles: An explanatory approach, through which the reader is motivated to understand the subject and not just learn the facts; A mechanistic approach, giving the reader the power to understand compounds and reactions never previously encountered; An evidence-based approach, setting out clearly how and why reactions happen as they do, giving extra depth to the reader's understanding. The authors write clearly and directly, sharing with the reader their own fascination with the subject, and leading them carefully from topic to topic. Their honest and open narrative flags pitfalls and misconceptions, guiding the reader towards a complete picture of organic chemistry and its universal themes and principles. Enriched with an extensive bank of online resources to help the reader visualise the structure of organic compounds and their reaction mechanisms, this second edition reaffirms the position of Organic Chemistry as the essential course companion for all organic chemistry students. Online Resource Centre For students: A range of problems to accompany each chapter For registered adopters of the text: Figures from the book in electronic format.

 

 

 

 

 

 

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Abbreviations xv

 

Preface to the second edition xvii

 

Organic chemistry and this book xix

 

1 What is organic chemistry? 1

 

2 Organic structures 15

 

3 Determining organic structures 43

 

4 Structure of molecules 80

 

5 Organic reactions 107

 

6 Nucleophilic addition to the carbonyl group 125

 

7 Delocalization and conjugation 141

 

8 Acidity, basicity, and p/Ca 163

 

9 Using organometallic reagents to make C-C bonds 182

 

10 Nucleophilic substitution at the carbonyl group 197

 

11 Nucleophilic substitution at C=O with loss of carbonyl oxygen 222

 

12 Equilibria, rates, and mechanisms 240

 

13 1H NMR: Proton nuclear magnetic resonance 269

 

14 Stereochemistry 302

 

15 Nucleophilic substitution at saturated carbon 328

 

16 Conformational analysis 360

 

17 Elimination reactions 382

 

18 Review of spectroscopic methods 407

 

19 Electrophilic addition to alkenes 427

 

20 Formation and reactions of enols and enolates 449

 

21 Electrophilic aromatic substitution 471

 

22 Conjugate addition and nucleophilic aromatic substitution 498

 

23 Chemoselectivity and protecting groups 528

 

24 Regioselectivity 562

 

25 Alkylation of enolates 584

 

26 Reactions of enolates with carbonyl compounds: the aldol and Claisen reactions 614

 

27 Sulfur, silicon, and phosphorus in organic chemistry 656

 

28 Retrosynthetic analysis 694

 

29 Aromatic heterocycles 1: reactions 723

 

30 Aromatic heterocycles 2: synthesis 757

 

31 Saturated heterocycles and stereoelectronics 789

 

32 Stereoselectivity in cyclic molecules 825

 

33 Diastereoselectivity 852

 

34 Pericyclic reactions 1: cycloadditions 877

 

35 Pericyclic reactions 2: sigmatropic and electrocydic reactions 909

 

36 Participation, rearrangement, and fragmentation 931

 

37 Radical reactions 970

 

38 Synthesis and reactions of carbenes 1003

 

39 Determining reaction mechanisms 1029

 

40 Organometallic chemistry 1069

 

41 Asymmetric synthesis 1102

 

42 Organic chemistry of life 1134

 

43 Organic chemistry today 1169

 

Figure acknowledgements 1182

 

Periodic table of the elements 1184

 

Index 1187