| Preface |
| A Note for Students |
| Structure and Bonding; Acids and Bases / 1： |
| Atomic Structure / 1.1： |
| Electron Configuration of Atoms / 1.2： |
| Development of Chemical Bonding Theory / 1.3： |
| The Nature of Chemical Bonds / 1.4： |
| Forming Covalent Bonds: Valence Bond Theory / 1.5： |
| Hybridization: sp[superscript 3] Orbitals and the Structure of Methane / 1.6： |
| Hybridization: sp[superscript 3] Orbitals and the Structure of Ethane / 1.7： |
| Hybridization: sp[subscript 2] Orbitals and the Structure of Ethylene / 1.8： |
| Hybridization: sp Orbitals and the Structure of Acetylene / 1.9： |
| Polar Covalent Bonds: Electronegativity / 1.10： |
| Acids and Bases: The Bronsted--Lowry Definition / 1.11： |
| Acids and Bases: The Lewis Definition / 1.12： |
| The Nature of Organic Compounds: Alkanes / 2： |
| Functional Groups / 2.1： |
| Alkanes and Alkyl Groups: Isomers / 2.2： |
| Naming Branched-Chain Alkanes / 2.3： |
| Properties of Alkanes / 2.4： |
| Conformations of Ethane / 2.5： |
| Drawing Chemical Structures / 2.6： |
| Cycloalkanes / 2.7： |
| Cis--Trans Isomerism in Cycloalkanes / 2.8： |
| Conformations of Some Cycloalkanes / 2.9： |
| Axial and Equatorial Bonds in Cyclohexane / 2.10： |
| Conformational Mobility of Cyclohexane / 2.11： |
| The Nature of Organic Reactions: Alkenes / 3： |
| Naming Alkenes / 3.1： |
| Electronic Structure of Alkenes / 3.2： |
| Cis--Trans Isomers of Alkenes / 3.3： |
| Sequence Rules: The E,Z Designation / 3.4： |
| Kinds of Organic Reactions / 3.5： |
| How Reactions Occur: Mechanisms / 3.6： |
| The Mechanism of an Organic Reaction: Addition of HCl to Ethylene / 3.7： |
| Describing a Reaction: Reaction Energy Diagrams and Transition States / 3.8： |
| Describing a Reaction: Intermediates / 3.9： |
| Reactions of Alkenes and Alkynes / 4： |
| Addition of HX to Alkenes: Hydrohalogenation / 4.1： |
| Orientation of Alkene Addition Reactions: Markovnikov's Rule / 4.2： |
| Carbocation Structure and Stability / 4.3： |
| Addition of H[subscript 2]O to Alkenes: Hydration / 4.4： |
| Addition of X[subscript 2] to Alkenes: Halogenation / 4.5： |
| Addition of H[subscript 2] to Alkenes: Hydrogenation / 4.6： |
| Oxidation of Alkenes: Hydroxylation and Cleavage / 4.7： |
| Biological Addition Reactions of Alkenes / 4.8： |
| Addition of Radicals to Alkenes: Polymers / 4.9： |
| Conjugated Dienes / 4.10： |
| Stability of Allylic Carbocations: Resonance / 4.11： |
| Drawing and Interpreting Resonance Forms / 4.12： |
| Alkynes and Their Reactions / 4.13： |
| Aromatic Compounds / 5： |
| Structure of Benzene: The Kekule Proposal / 5.1： |
| Structure of Benzene: The Resonance Proposal / 5.2： |
| Naming Aromatic Compounds / 5.3： |
| Electrophilic Aromatic Substitution Reactions: Bromination / 5.4： |
| Other Electrophilic Aromatic Substitution Reactions / 5.5： |
| The Friedel--Crafts Alkylation and Acylation Reactions / 5.6： |
| Substituent Effects in Electrophilic Aromatic Substitution / 5.7： |
| An Explanation of Substituent Effects / 5.8： |
| Oxidation and Reduction of Aromatic Compounds / 5.9： |
| Polycyclic Aromatic Hydrocarbons / 5.10： |
| Organic Synthesis / 5.11： |
| Stereochemistry / 6： |
| Stereochemistry and the Tetrahedral Carbon / 6.1： |
| The Reason for Handedness in Molecules: Chirality / 6.2： |
| Optical Activity / 6.3： |
| Specific Rotation / 6.4： |
| Pasteur's Discovery of Enantiomers / 6.5： |
| Sequence Rules for Specifying Configuration / 6.6： |
| Diastereomers / 6.7： |
| Meso Compounds / 6.8： |
| Molecules with More Than Two Stereocenters / 6.9： |
| Racemic Mixtures and the Resolution of Enantiomers / 6.10： |
| Physical Properties of Stereoisomers / 6.11： |
| A Brief Review of Isomerism / 6.12： |
| Chirality in Nature / 6.13： |
| Alkyl Halides / 7： |
| Naming Alkyl Halides / 7.1： |
| Preparing Alkyl Halides / 7.2： |
| Reactions of Alkyl Halides: Grignard Reagents / 7.3： |
| Nucleophilic Substitution Reactions / 7.4： |
| The S[subscript N]2 Reaction / 7.5： |
| The S[subscript N]1 Reaction / 7.6： |
| Eliminations: The E2 Reaction / 7.7： |
| Eliminations: The E1 Reaction / 7.8： |
| A Summary of Reactivity: S[subscript N]1, S[subscript N]2, E1, E2 / 7.9： |
| Substitution Reactions in Living Organisms / 7.10： |
| Alcohols, Phenols, and Ethers / 8： |
| Naming Alcohols, Phenols, and Ethers / 8.1： |
| Properties of Alcohols, Phenols, and Ethers: Hydrogen Bonding / 8.2： |
| Properties of Alcohols and Phenols: Acidity / 8.3： |
| Synthesis of Alcohols / 8.4： |
| Reactions of Alcohols / 8.5： |
| Synthesis and Reactions of Phenols / 8.6： |
| Synthesis and Reactions of Ethers / 8.7： |
| Cyclic Ethers: Epoxides / 8.8： |
| Thiols and Sulfides / 8.9： |
| Aldehydes and Ketones: Nucleophilic Addition Reactions / 9： |
| The Nature of Carbonyl Compounds / 9.1： |
| Naming Aldehydes and Ketones / 9.2： |
| Synthesis of Aldehydes and Ketones / 9.3： |
| Oxidation of Aldehydes / 9.4： |
| Nucleophilic Addition Reactions of Aldehydes and Ketones: Reduction / 9.5： |
| Nucleophilic Addition of Water: Hydration / 9.6： |
| Nucleophilic Addition of Alcohols: Acetal Formation / 9.7： |
| Nucleophilic Addition of Amines: Imine Formation / 9.8： |
| Nucleophilic Addition of Grignard Reagents: Alcohol Formation / 9.9： |
| Conjugate Nucleophilic Addition Reactions / 9.10： |
| Some Biological Nucleophilic Addition Reactions / 9.11： |
| Carboxylic Acids and Derivatives / 10： |
| Naming Carboxylic Acids and Derivatives / 10.1： |
| Occurrence and Properties of Carboxylic Acids / 10.2： |
| Synthesis of Carboxylic Acids / 10.3： |
| Nucleophilic Acyl Substitution Reactions / 10.4： |
| Reactions of Carboxylic Acids / 10.5： |
| Chemistry of Acid Halides / 10.6： |
| Chemistry of Acid Anhydrides / 10.7： |
| Chemistry of Esters / 10.8： |
| Chemistry of Amides / 10.9： |
| Chemistry of Nitriles / 10.10： |
| Polymers from Carbonyl Compounds: Nylons and Polyesters / 10.11： |
| Carbonyl Alpha-Substitution Reactions and Condensation Reactions / 11： |
| Keto--Enol Tautomerism / 11.1： |
| Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions / 11.2： |
| Alpha Halogenation of Aldehydes and Ketones / 11.3： |
| Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation / 11.4： |
| Reactivity of Enolate Ions / 11.5： |
| Alkylation of Enolate Ions / 11.6： |
| Carbonyl Condensation Reactions / 11.7： |
| Condensations of Aldehydes and Ketones: The Aldol Reaction / 11.8： |
| Dehydration of Aldol Products: Synthesis of Enones / 11.9： |
| Condensations of Esters: The Claisen Condensation Reaction / 11.10： |
| Biological Carbonyl Reactions / 11.11： |
| Amines / 12： |
| Naming Amines / 12.1： |
| Structure and Properties of Amines / 12.2： |
| Basicity of Amines / 12.3： |
| Synthesis of Amines / 12.4： |
| Reactions of Amines / 12.5： |
| Heterocyclic Amines / 12.6： |
| Alkaloids: Naturally Occurring Amines / 12.7： |
| Structure Determination / 13： |
| Infrared Spectroscopy and the Electromagnetic Spectrum / 13.1： |
| Infrared Spectroscopy of Organic Molecules / 13.2： |
| Ultraviolet Spectroscopy / 13.3： |
| Interpreting Ultraviolet Spectra: The Effect of Conjugation / 13.4： |
| Nuclear Magnetic Resonance Spectroscopy / 13.5： |
| The Nature of NMR Absorptions / 13.6： |
| Chemical Shifts / 13.7： |
| Chemical Shifts in [superscript 1]H NMR Spectra / 13.8： |
| Integration of [superscript 1]H NMR Spectra: Proton Counting / 13.9： |
| Spin--Spin Splitting in [superscript 1]H NMR Spectra / 13.10： |
| Uses of [superscript 1]H NMR Spectra / 13.11： |
| [superscript 13]C NMR Spectroscopy / 13.12： |
| Biomolecules: Carbohydrates / 14： |
| Classification of Carbohydrates / 14.1： |
| Configurations of Monosaccharides: Fischer Projections / 14.2： |
| D,L Sugars / 14.3： |
| Configurations of Aldoses / 14.4： |
| Cyclic Structures of Monosaccharides: Hemiacetal Formation / 14.5： |
| Monosaccharide Anomers: Mutarotation / 14.6： |
| Reactions of Monosaccharides / 14.7： |
| Polysaccharides / 14.9： |
| Other Important Carbohydrates / 14.10： |
| Cell-Surface Carbohydrates and Carbohydrate Vaccines / 14.11： |
| Biomolecules: Amino Acids, Peptides, and Proteins / 15： |
| Structures of Amino Acids / 15.1： |
| Isoelectric Points / 15.2： |
| Peptides and Proteins / 15.3： |
| Covalent Bonding in Peptides / 15.4： |
| Peptide Structure Determination: Amino Acid Analysis / 15.5： |
| Peptide Sequencing: The Edman Degradation / 15.6： |
| Peptide Synthesis / 15.7： |
| Classification of Proteins / 15.8： |
| Protein Structure / 15.9： |
| Enzymes / 15.10： |
| How Do Enzymes Work? Citrate Synthase / 15.11： |
| Biomolecules: Lipids and Nucleic Acids / 16： |
| Lipids / 16.1： |
| Fats and Oils / 16.2： |
| Soaps / 16.3： |
| Phospholipids / 16.4： |
| Steroids / 16.5： |
| Nucleic Acids and Nucleotides / 16.6： |
| Structure of DNA / 16.7： |
| Base Pairing in DNA: The Watson--Crick Model / 16.8： |
| Nucleic Acids and Heredity / 16.9： |
| Replication of DNA / 16.10： |
| Structure and Synthesis of RNA: Transcription / 16.11： |
| RNA and Protein Biosynthesis: Translation / 16.12： |
| Sequencing DNA / 16.13： |
| The Polymerase Chain Reaction / 16.14： |
| The Organic Chemistry of Metabolic Pathways / 17： |
| An Overview of Metabolism and Biochemical Energy / 17.1： |
| Catabolism of Fats: [beta]-Oxidation Pathway / 17.2： |
| Catabolism of Carbohydrates: Glycolysis / 17.3： |
| The Citric Acid Cycle / 17.4： |
| Catabolism of Proteins: Transamination / 17.5： |
| The Organic Chemistry of Metabolic Pathways: A Summary / 17.6： |
| Appendixes |
| Nomenclature of Polyfunctional Organic Compounds / A： |
| Glossary / B： |
| Answers to Selected In-Chapter Problems / C： |
| Index |
図書
