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