Chapter 1. Atomic and Molecular Structure Interchapter A. Nomenclature: The Basic System for Naming Organic Compounds, Alkanes, Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers Chapter 2. Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties Chapter 3. Valence Bond Theory and Molecular Orbital Theory Interchapter B. Naming Alkenes, Alkynes, and Benzene Derivatives Chapter 4. Isomerism 1: Conformers and Constitutional Isomers Chapter 5. Isomerism 2: Chirality, Enantiomers, and Diastereomers Chapter 6. The Proton Transfer Reaction: An Introduction to Mechanisms, Equilibria, Free Energy Diagrams, and Charge Stability Chapter 7. An Overview of the Most Common Elementary Steps Interchapter C. Molecular Orbital Theory and Chemical Reactions Interchapter D. Naming Compounds with a Functional Group that Calls for a Suffix: Alcohols, Amines, Ketones, Aldehydes, Carboxylic Acids, and Carboxylic Acid Derivatives Chapter 8. An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions Chapter 9. Nucleophilic Substitution and Elimination Reactions 1: Competition among SN2, SN1, E2, and E1 Reactions Chapter 10. Organic Synthesis 1: Nucleophilic Substitution and Elimination Reactions and Functional Group Transformations Chapter 11. Organic Synthesis 2: Beginning Concepts in Designing Multistep Synthesis Chapter 12. Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted Acid Chapter 13. Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving Cyclic Transition States Chapter 14. Conjugation and Aromaticity Chapter 15. Structure Determination 1: Mass Spectrometry Chapter 16. Structure Determination 1: Infrared Spectroscopy and Ultraviolet–Visible Spectroscopy Chapter 17. Structure Determination 3: Nuclear Magnetic Resonance Spectroscopy Chapter 18. Nucleophilic Addition to Polar π Bonds 1: Addition of Strong Nucleophiles Chapter 19. Nucleophilic Addition to Polar π Bonds 2: Weak Nucleophiles and Acid and Base Catalysis Chapter 20. Redox Reactions: Organometallic Reagents and Their Reactions Chapter 21. Organic Synthesis 3: Intermediate Topics in Synthesis Design Chapter 22. Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involving Strong Nucleophiles Chapter 23. Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles Chapter 24. Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful Accompanying Reactions Chapter 25. Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings Chapter 26. The Diels–Alder Reaction, Syn Dihydroxylation, and Oxidative Cleavage Chapter 27. Reactions Involving Radicals Chapter 28. Polymers Chapter 29. (EBOOK ONLY) Biomolecules 1: An Overview of the Structure, Chemical Properties, and Roles of the Molecules of Life Chapter 30. (EBOOK ONLY) Biomolecules 2: Representative Biochemical Processes Involving Biomolecules Appendix on Trivial Names