Preface Structure and Bonding in Organic Molecules Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity Cycloalkanes Stereoisomers Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination Hydroxy Functional Group: Alcohols: Properties, Preparation, and Strategy of Synthesis Further Reactions of Alcohols and the Chemistry of Ethers Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure Alkenes and Infrared Spectroscopy Reactions of Alkenes Alkynes: The Carbon-Carbon Triple Bond Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy Benzene and Aromaticity: Electrophilic Aromatic Substitution Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity Aldehydes and Ketones: The Carbonyl Group Enols, Enolates and the Aldol Condensation: I ,I -Unsaturated Aldehydes and Ketones Carboxylic Acids Carboxylic Acid Derivatives Amines and Their Derivatives: Functional Groups Containing Nitrogen Chemistry of Benzene Substituents: Alkylbenzenes, Phenols, and Benzamines Enolates and the Claisen Condensation: Synthesis of I -Dicarbonyl Compounds: Acyl Anion Equivalents Carbohydrates: Polyfunctional Compounds in Nature Heterocycles: Heteroatoms in Cyclic Organic Compounds Amino Acids, Peptides, Proteins, and Nucleic Acids: Nitrogen-Containing Polymers in Nature MCAT Questions Answers to Exercises Photograph Credits Index