1 The Basics: Bonding and Molecular Structure 1 2 Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy 53 3 An Introduction to Organic Reactions and Their Mechanisms: Acids and Bases 105 4 Nomenclature and Conformations of Alkanes and Cycloalkanes 147 5 Stereochemistry: Chiral Molecules 197 6 Nucleophilic Reactions: Properties and Substitution Reactions of Alkyl Halides 243 7 Alkenes and Alkynes I: Properties and Synthesis. Elimination Reactions of Alkyl Halides 285 8 Alkenes and Alkynes II: Addition and Oxidation Reactions 341 9 Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination 397 10 Radical Reactions 453 11 Alcohols and Ethers: Synthesis and Reactions 493 12 Alcohols from Carbonyl Compounds: Oxidation–Reduction and Organometallic Compounds 541 13 Conjugated Unsaturated Systems 579 14 Aromatic Compounds 627 15 Reactions of Aromatic Compounds 669 16 Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 723 17 Carboxylic Acids and Their Derivatives: Nucleophilic Addition–Elimination at the Acyl Carbon 773 18 Reactions at the α Carbon of Carbonyl Compounds: Enols and Enolates 825 19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds: More Chemistry of Enolates 861 20 Amines 903 21 Transition Metal Complexes: Promoters of Key Bond-Forming Reactions 951 22 Carbohydrates 979 23 Lipids 1027 24 Amino Acids and Proteins 1063 25 Nucleic Acids and Protein Synthesis 1109 Glossary Gl- 1 Index I- 1