ORGANIC CHEMISTRY

SECOND EDITION

Jonathan Clayden, University of Manchester

Nick Greeves, University of Liverpool

Stuart Warren, University of Cambridge

Brief Contents [Chapter vise]

1. What is organic chemistry?

2. Organic structures

3. Determining organic structures

4. Structure of molecules

5. Organic reactions

6. Nucleophilic addition to the carbonyl group

7. Delocalization and conjugation

8. Acidity, basicity, and pKa

9. Using organometallic reagents to make C–C bonds

10. Nucleophilic substitution at the carbonyl group

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

12. Equilibria, rates, and mechanisms

13. 1H NMR: Proton nuclear magnetic resonance

14. Stereochemistry

15. Nucleophilic substitution at saturated carbon

16. Conformational analysis

17. Elimination reactions

18. Review of spectroscopic methods

19. Electrophilic addition to alkenes

20. Formation and reactions of enols and enolates

21. Electrophilic aromatic substitution

22. Conjugate addition and nucleophilic aromatic substitution

23. Chemoselectivity and protecting groups

24. Regioselectivity

25. Alkylation of enolates

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

27. Sulfur, silicon, and phosphorus in organic chemistry

28. Retrosynthetic analysis

29. Aromatic heterocycles 1: reactions

30. Aromatic heterocycles 2: synthesis

31. Saturated heterocycles and stereoelectronics

32. Stereoselectivity in cyclic molecules

33. Diastereoselectivity

34. Pericyclic reactions 1: cycloadditions

35. Pericyclic reactions 2: sigmatropic and electrocyclic reactions

36. Participation, rearrangement, and fragmentation

37. Radical reactions

38. Synthesis and reactions of carbenes

39. Determining reaction mechanisms

40. Organometallic chemistry

41. Asymmetric synthesis

42. Organic chemistry of life

43. Organic chemistry today

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