This innovative text highlights mechanistic similarities and ties synthesis and reactivity together. This fifth edition includes a new chapter on amines, summaries for every chapter and has more problems throughout.

Includes index.

1. Electronic structures and bonding. Acids and bases -- 2. An introduction to organic compounds: Nomenclature, physical properties, and representation of structure -- 3. Alkenes: Structure, nomenclature, and an introduction to reactivity. Thermodynamics and kinetics -- 4. The reactions of alkenes -- 5. Stereochemistry: the arrangement of atoms in space; The stereochemistry of addition reactions -- 6. The reactions of alkynes: an introduction to multistep synthesis -- 7. Delocalized electrons and their effect on stability, reactivity and pKa. More about molecular orbital theory -- 8. Substitution reactions of alkyl halides -- 9. Elimination reactions of alkyl halides. Competition between substitution and elimination -- 10. Reactions of alcohols, amines, ethers, epoxides and sulfur-containing compounds. Organometallic compounds -- 11. Radicals. Reactions of alkanes -- 12. Mass spectrometry, infrared spectroscopy, and ultraviolet/visible spectroscopy. 13. NMR spectroscopy -- 14. Aromaticity. Reactions of benzene -- 15. Reactions of substituted benzenes -- 16. Carbonyl compounds I. Nucleophilic acyl substitution -- 17. Carbonyl compounds II. Reactions of aldehydes and ketones. More reactions of carboxylic acid derivatives. Reactions of alpha, beta-unsaturated carbonyl compounds -- 18. Carbonyl compounds III. Reactions at the alpha-carbon -- 19. More about oxidation-reduction reactions -- 20. More about amines. Heterocyclic compounds -- 21. Carbohydrates -- 22. Amino acids, peptides, and proteins -- 23. Catalysis -- 24. The organic mechanisms of the coenzymes -- 25. The chemistry of metabolism -- 26. Lipids -- 27. Nucleosides, nucleotides, and nucleic acids -- 28. Synthetic polymers -- 29. Pericyclic reactions. -- 30. The organic chemistry of drugs: Discovery and design -- Appendices.