Table of Contents

1. Structure and Bonding.
2. Polar Covalent Bonds; Acids and Bases.
3. Organic Compounds: Alkanes and Their Stereochemistry.
4. Organic Compounds: Cycloalkanes and Their Stereochemistry
5. Stereochemistry at Tetrahedral Centers.
6. An Overview of Organic Reactions.
7. Alkenes: Structure and Reactivity.
Practice Your Scientific Analysis and Reasoning I: The Chiral Drug Thalidomide
8. Alkenes: Reactions and Synthesis.
9. Alkynes: An Introduction to Organic Synthesis.
10. Organohalides.
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations.
Practice Your Scientific Analysis and Reasoning II: From Mustard Gas to Alkylating Anticancer Drugs
12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy.
13. Structure Determination: Nuclear Magnetic Resonance Spectroscopy.
14. Conjugated Compounds and Ultraviolet Spectroscopy.
15. Benzene and Aromaticity.
Practice Your Scientific Analysis and Reasoning III: Photodynamic Therapy (PDT)
16. Chemistry of Benzene: Electrophilic Aromatic Substitution.
17. Alcohols and Phenols.
18. Ethers and Epoxides; Thiols and Sulfides.
Preview of Carbonyl Chemistry.
19. Aldehydes and Ketones: Nucleophilic Addition Reactions.
Practice Your Scientific Analysis and Reasoning IV: SSRIs
20. Carboxylic Acids and Nitriles.
21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions.
22. Carbonyl Alpha-Substitution Reactions.
23. Carbonyl Condensation Reactions.
Practice Your Scientific Analysis and Reasoning V: Thymine in DNA
24. Amines and Heterocycles.
25. Biomolecules: Carbohydrates.
26. Biomolecules: Amino Acids, Peptides, and Proteins.
Practice Your Scientific Analysis and Reasoning VI: Melatonin and Serotonin
27. Biomolecules: Lipids.
28. Biomolecules: Nucleic Acids.
29. The Organic Chemistry of Metabolic Pathways.
30. Orbitals and Organic Chemistry: Pericyclic Reactions.
31. Synthetic Polymers.
Practice Your Scientific Analysis and Reasoning VII: The Potent Antibiotic of Endiandric Acid C.

About the Author

John E. McMurry, Ph.D., received his Bachelor of Arts from Harvard University and his doctorate at Columbia University. He is an American Association for the Advancement of Science Fellow and an Alfred P. Sloan Research Foundation Fellow. He has received several awards, including the National Institutes of Health Career Development Award, the Alexander von Humboldt Senior Scientist Award, and the Max Planck Research Award. In addition to ORGANIC CHEMISTRY, he is also the author or coauthor of ORGANIC CHEMISTRY: A BIOLOGICAL APPROACH; FUNDAMENTALS OF ORGANIC CHEMISTRY; and THE ORGANIC CHEMISTRY OF BIOLOGICAL PATHWAYS.