Organic Chemistry, International Edition

William H. Brown is emeritus professor of chemistry at Beloit College, where he was twice named Teacher of the Year. His teaching responsibilities include organic chemistry, advanced organic chemistry, and, more recently, special topics in pharmacology and drug synthesis. He received his Ph.D. from Columbia University under the direction of Gilbert Stork and did postdoctoral work at California Institute of Technology and the University of Arizona. Eric Anslyn received his Ph.D. from the California Institute of Technology and is the Norman Hackerman Professor of Chemistry and a University Distinguished Teaching Professor at The University of Texas at Austin. Anslyn's research focuses on the physicals and bioorganic chemistry of synthetic and natural receptors and catalysts. Brent L. Iverson received his Ph.D. from the California Institute of Technology. He is a University Distinguished Teaching Professor and the Dean of the School of Undergraduate Studies at University of Texas at Austin, as well as a respected researcher. His research spans the interface of organic chemistry and molecular biology. His group has developed several patented technologies, including an FDA-approved treatment for late-stage anthrax. Christopher S. Foote was a professor of chemistry at the University of California, Los Angeles. His scholarly credits included Sloan Fellow; Guggenheim Fellow; ACS Baekland Award; ACS Cope Scholar; Southern California Section ACS Tolman Medal; President, American Society for Photobiology; and Senior Editor, Accounts of Chemical Research.

• 1. Covalent Bonding and Shapes of Molecules.2. Alkanes and Cycloalkanes.3. Stereochemistry and Chirality.4. Acids and Bases.5. Alkenes.Primer I: Reaction Mechanisms6. Reactions of Alkenes.7. Alkynes.8. Haloalkanes, Halogenation, and Radical Reactions.9. Nucleophilic Substitution and B-Elimination.10. Alcohols.11. Ethers, Sulfides, and Epoxides.12. Infrared Spectroscopy.13. Nuclear Magnetic Resonance Spectroscopy.14. Mass Spectrometry.15. Introduction to Organometallic Compounds.16. Aldehydes and Ketones.17. Carboxylic Acids.Primer II: Carboxylic Acid Derivative Reaction Mechanisms.18. Functional Derivatives of Carboxylic Acids.19. Enolate Anions and Enamines.20. Dienes, Conjugated Systems, and Pericyclic Reactions.21. Benzene and the Concept of Aromaticity.22. Reactions of Benzene and Its Derivatives.23. Amines.24. Catalytic Carbon–Carbon Bond Formation.25. Carbohydrates.26: Lipids.27. Amino Acids and Proteins.28. Nucleic Acids.29. Organic Polymer Chemistry.Appendices:1. Thermodynamics and the Equilibrium Constant.2. Major Classes of Organic Acids.3. Bond Dissociation Enthalpies.4. Characteristic 1H-NMR Chemical Shifts.5. Characteristic 13C Chemical Shifts.6. Characteristic IR Absorption Frequencies.7. Electrostatic Potential Maps.8. Summary of Stereochemical Terms.9. Summary of the Rules of Nomenclature.10. Common Mistakes in Arrow Pushing.11. Organic Chemistry Roadmaps.GLOSSARY G-1.INDEX I-1.

1. Covalent Bonding and Shapes of Molecules. 2. Alkanes and Cycloalkanes. 3. Stereochemistry and Chirality. 4. Acids and Bases. 5. Alkenes. Primer I: Reaction Mechanisms 6. Reactions of Alkenes. 7. Alkynes. 8. Haloalkanes, Halogenation, and Radical Reactions. 9. Nucleophilic Substitution and B-Elimination. 10. Alcohols. 11. Ethers, Sulfides, and Epoxides. 12. Infrared Spectroscopy. 13. Nuclear Magnetic Resonance Spectroscopy. 14. Mass Spectrometry. 15. Introduction to Organometallic Compounds. 16. Aldehydes and Ketones. 17. Carboxylic Acids. Primer II: Carboxylic Acid Derivative Reaction Mechanisms. 18. Functional Derivatives of Carboxylic Acids. 19. Enolate Anions and Enamines. 20. Dienes, Conjugated Systems, and Pericyclic Reactions. 21. Benzene and the Concept of Aromaticity. 22. Reactions of Benzene and Its Derivatives. 23. Amines. 24. Catalytic Carbon-Carbon Bond Formation. 25. Carbohydrates. 26: Lipids. 27. Amino Acids and Proteins. 28. Nucleic Acids. 29. Organic Polymer Chemistry. Appendices: 1. Thermodynamics and the Equilibrium Constant. 2. Major Classes of Organic Acids. 3. Bond Dissociation Enthalpies. 4. Characteristic 1H-NMR Chemical Shifts. 5. Characteristic 13C Chemical Shifts. 6. Characteristic IR Absorption Frequencies. 7. Electrostatic Potential Maps. 8. Summary of Stereochemical Terms. 9. Summary of the Rules of Nomenclature. 10. Common Mistakes in Arrow Pushing. 11. Organic Chemistry Roadmaps. GLOSSARY G-1. INDEX I-1.