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| Preface | |
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| About the Author | |
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| Chemical Bonding and Chemical Structure | |
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| Introduction | |
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| Classical Theories of Chemical Bonding | |
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| Structures of Covalent Compounds | |
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| Resonance Structures | |
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| Wave Nature of the Electron | |
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| Electronic Structure of the Hydrogen Atom | |
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| Electronic Structures of More Complex Atoms | |
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| Another Look at the Covalent Bond: Molecular Orbitals | |
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| Hybrid Orbitals | |
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| Key Ideas in Chapter 1 | |
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| Additional Problems | |
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| Alkanes | |
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| Hydrocarbons | |
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| Unbranched Alkanes | |
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| Conformations of Alkanes | |
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| Constitutional Isomers and Nomenclature | |
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| Cycloalkanes and Skeletal Structures | |
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| Physical Properties of Alkanes | |
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| Combustion and Elemental Analysis | |
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| Occurrence and Use of Alkanes | |
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| Functional Groups, Compound Classes, and the "R" Notation | |
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| Key Ideas in Chapter 2 | |
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| Additional Problems | |
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| Acids and Bases: The Curved-Arrow Notation | |
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| Lewis Acid-Base Association Reactions | |
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| Electron-Pair Displacement Reactions | |
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| Review of the Curved-Arrow Notation | |
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| Bronsted-Lowry Acids and Bases | |
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| Free Energy and Chemical Equilibrium | |
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| Relationship of Structure to Acidity | |
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| Key Ideas in Chapter 3 | |
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| Additional Problems | |
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| Introduction to Alkenes: Structure and Reactivity | |
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| Structure and Bonding in Alkenes | |
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| Nomenclature of Alkenes | |
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| Unsaturation Number | |
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| Physical Properties of Alkenes | |
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| Relative Stabilities of Alkene Isomers | |
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| Addition Reactions of Alkenes | |
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| Addition of Hydrogen Halides to Alkenes | |
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| Reaction Rates | |
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| Catalysis | |
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| Key Ideas in Chapter 4 | |
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| Additional Problems | |
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| Addition Reactions of Alkenes | |
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| Reactions of Alkenes with Halogens | |
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| Writing Organic Reactions | |
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| Conversion of Alkenes Into Alcohols | |
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| Ozonolysis of Alkenes | |
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| Free-Radical Addition of Hydrogen Bromide to Alkenes | |
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| Polymers: Free-Radical Polymerization of Alkenes | |
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| Alkenes in the Chemical Industry | |
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| Key Ideas in Chapter 5 | |
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| Additional Problems | |
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| Principles of Stereochemistry | |
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| Enantiomers, Chirality, and Symmetry | |
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| Nomenclature of Enantiomers: The R,S System | |
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| Physical Properties of Enantiomers: Optical Activity | |
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| Racemates | |
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| Stereochemical Correlation | |
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| Diastereomers | |
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| Meso Compounds | |
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| Enantiomeric Resolution | |
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| Chiral Molecules Without Asymmetric Atoms | |
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| Conformational Stereoisomers | |
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| Fischer Projections | |
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| The Postulation of Tetrahedral Carbon | |
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| Key Ideas in Chapter 6 | |
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| Additional Problems | |
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| Cyclic Compounds: Stereochemistry of Reactions | |
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| Relative Stabilities of the Monocyclic Alkanes | |
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| Conformations of Cyclohexane | |
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| Monosubstituted Cyclohexanes: Conformational Analysis | |
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| Disubstituted Cyclohexanes | |
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| Cyclopentane, Cyclobutane, and Cyclopropane | |
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| Bicyclic and Polycyclic Compounds | |
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| Relative Reactivities of Stereoisomers | |
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| Reactions That Form Stereoisomers | |
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| Stereochemistry of Chemical Reactions | |
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| Key Ideas in Chapter 7 | |
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| Additional Problems | |
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| Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides | |
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| Nomenclature | |
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| Structures | |
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| Effect of Molecular Polarity and Hydrogen Bonding on Physical Properties | |
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| Solvents in Organic Chemistry | |
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| Applications of Solubility and Solvation Principles | |
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| Acidity of Alcohols and Thiols | |
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| Basicity of Alcohols and Ethers | |
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| Grignard and Organolithium Reagents | |
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| Industrial Preparation and Use of Alkyl Halides, Alcohols, and Ethers | |
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| Key Ideas in Chapter 8 | |
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| Additional Problems | |
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| Chemistry of Alkyl Halides | |
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| An Overview of Nucleophilic Substitution and [beta]-Elimination Reactions | |
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| Equilibrium in Nucleophilic Substitution Reactions | |
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| Reaction Rates | |
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| The S[subscript N]2 Reaction | |
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| The E2 Reaction | |
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| The S[subscript N]1 and E1 Reactions | |
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| Summary of Substitution and Elimination Reactions of Alkyl Halides | |
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| Carbenes and Carbenoids | |
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| Key Ideas in Chapter 9 | |
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| Additional Problems | |
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| Chemistry of Alcohols and Thiols | |
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| Dehydration of Alcohols | |
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| Reactions of Alcohols with Hydrogen Halides | |
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| Sulfonate and Inorganic Ester Derivatives of Alcohols | |
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| Conversion of Alcohols into Alkyl Halides: Summary | |
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| Oxidation and Reduction in Organic Chemistry | |
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| Oxidation of Alcohols | |
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| Biological Oxidation of Ethanol | |
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| Chemical and Stereochemical Group Equivalence | |
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| Oxidation of Thiols | |
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| Synthesis of Alcohols | |
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| Design of Organic Synthesis | |
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| Key Ideas in Chapter 10 | |
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| Additional Problems | |
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| Chemistry of Ethers, Epoxides, Glycols, and Sulfides | |
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| Synthesis of Ethers and Sulfides | |
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| Synthesis of Epoxides | |
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| Cleavage of Ethers | |
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| Nucleophilic Substitution Reactions of Epoxides | |
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| Preparation and Oxidative Cleavage of Glycols | |
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| Oxonium and Sulfonium Salts | |
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| Neighboring-Group Participation: Intramolecular Reactions | |
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| Oxidation of Ethers and Sulfides | |
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| The Three Fundamental Operations of Organic Synthesis | |
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| Key Ideas in Chapter 11 | |
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| Additional Problems | |
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| Introduction to Spectroscopy: Infrared Spectroscopy and Mass Spectrometry | |
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| Introduction to Spectroscopy | |
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| Infrared Spectroscopy | |
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| Infrared Absorption and Chemical Structure | |
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| Functional-Group Infrared Absorptions | |
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| The Infrared Spectrometer | |
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| Introduction to Mass Spectrometry | |
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| Key Ideas in Chapter 12 | |
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| Additional Problems | |
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| Nuclear Magnetic Resonance Spectroscopy | |
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| An Overview of Proton NMR Spectroscopy | |
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| Physical Basis of NMR Spectroscopy | |
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| The NMR Spectrum: Chemical Shift and Integral | |
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| The NMR Spectrum: Spin-Spin Splitting | |
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| Complex NMR Spectra | |
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| USE of Deuterium in Proton NMR | |
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| Characteristic Functional-Group NMR Absorptions | |
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| NMR Spectroscopy of Dynamic Systems | |
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| Carbon NMR | |
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| Solving Structure Problems with Spectroscopy | |
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| The NMR Spectrometer | |
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| Other uses of NMR | |
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| Key Idens in Chapter 13 | |
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| Additional Problems | |
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| Chemistry of Alkynes | |
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| Nomenclature of Alkynes | |
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| Structure and Bonding In Alkynes | |
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| Physical Properties of Alkynes | |
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| Introduction to Addition Reac Hons of the Triple Bond | |
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| Conversion of Alkynes Into Aldehydes and Ketones | |
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| Reduction of Alkynes | |
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| Acidity of 1-Alkynes | |
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| Organic Synthesis Using Alkynes | |
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| Pheromones | |
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| Occurrence and use of Alkynes | |
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| Key Ideas in Chapter 14 | |
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| Additional Problems | |
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| Dienes, Resonance, and Aromaticity | |
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| Structure and Stability of Dienes | |
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| Ultraviolet Spectroscopy | |
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| The Diels-Alder Reaction | |
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| Addition of Hydrogen Halides to Conjugated Dienes | |
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| Diene Polymers | |
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| Resonance | |
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| Introduction to Aromatic Compounds | |
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| Key Ideas in Chapter 15 | |
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| Additional Problems | |
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| Chemistry of Benzene and Its Derivatives | |
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| Nomenclature of Benzene Derivatives | |
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| Physical Properties of Benzene Derivatives | |
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| Spectroscopy of Benzene Derivatives | |
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| Electrophilic Aromatic Substitution Reactions of Benzene | |
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| Electrophilic Aromatic Substitution Reactions of Substituted Benzenes | |
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| Hydrogenation of Benzene Derivatives | |
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| Source and Industrial use of Aromatic Hydrocarbons | |
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| Key Ideas in Chapter 16 | |
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| Additional Problems | |
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| Allylic and Benzylic Reactivity | |
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| Reactions Involving Allylic and Benzylic Carbocations | |
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| Reactions Involving Allylic and Benzylic Radicals | |
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| Reactions Involving Allylic and Benzylic Anions | |
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| Allylic and Benzylic S[subscript N]2 Reactions | |
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| Benzylic Oxidation of Alkylbenzenes | |
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| Terpenes | |
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| Key Ideas in Chapter 17 | |
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| Additional Problems | |
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| Chemistry of Aryl Halides, Vinylic Halides, and Phenols: Transition-Metal Catalysis | |
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| Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]2 Conditions | |
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| Elimination Reactions of Vinylic Halides | |
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| Lack of Reactivity of Vinylic and Aryl Halides Under S[subscript N]1 Conditions | |
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| Nucleophilic Substitution Reactions of Aryl Halides | |
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| Transition-Metal Catalyzed Coupling Reactions | |
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| Acidity of Phenols | |
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| Oxidation of Phenols to Quinones | |
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| Electrophilic Aromatic Substitution Reactions of Phenols | |
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| Reactivity of the Aryl-Oxygen Bond | |
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| Industrial Preparation and use of Phenol | |
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| Key Ideas in Chapter 18 | |
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| Additional Problems | |
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| Chemistry of Aldehydes and Ketones: Carbonyl-Addition Reactions | |
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| Nomenclature of Aldehydes and Ketones | |
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| Physical Properties of Aldehydes and Ketones | |
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| Spectroscopy of Aldehydes and Ketones | |
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| Synthesis of Aldehydes and Ketones | |
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| Introduction to Aldehyde and Ketone Reactions | |
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| Basicity of Aldehydes and Ketones | |
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| Reversible Addition Reactions of Aldehydes and Ketones | |
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| Reduction of Aldehydes and Ketones to Alcohols | |
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| Reactions of Aldehydes and Ketones with Grignard and Related Reagents | |
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| Acetals and Their use as Protecting Groups | |
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| Reactions of Aldehydes and Ketones with Amines | |
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| Reduction of Carbonyl Groups to Methylene Groups | |
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| The Wittig Alkene Synthesis | |
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| Oxidation of Aldehydes to Carboxylic Acids | |
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| Manufacture and use of Aldehydes and Ketones | |
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| Key Ideas in Chapter 19 | |
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| Additional Problems | |
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| Chemistry of Carboxylic Acids | |
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| Nomenclature of Carboxylic Acids | |
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| Structure and Physical Properties of Carboxylic Acids | |
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| Spectroscopy of Carboxylic Acids | |
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| Acid-Base Properties of Carboxylic Acids | |
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| Fatty Acids, Soaps, and Detergents | |
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| Synthesis of Carboxylic Acids | |
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| Introduction to Carboxylic Acid Reactions | |
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| Conversion of Carboxylic Acids into Esters | |
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| Conversion of Carboxylic Acids into Acid Chlorides and Anhydrides | |
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| Reduction of Carboxylic Acids to Primary Alcohols | |
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| Decarboxylation of Carboxylic Acids | |
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| Key Ideas in Chapter 20 | |
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| Additional Problems | |
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| Chemistry of Carboxylic Acid Derivatives | |
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| Nomenclature and Classification of Carboxylic Acid Derivatives | |
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| Structures of Carboxylic Acid Derivatives | |
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| Physical Properties of Carboxylic Acid Derivatives | |
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| Spectroscopy of Carboxylic Acid Derivatives | |
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| Basicity of Carboxylic Acid Derivatives | |
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| Introduction to Reactions of Carboxylic Acid Derivatives | |
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| Hydrolysis of Carboxylic Acid Derivatives | |
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| Reactions of Carboxylic Acid Derivatives with Nucleophiles | |
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| Reduction of Carboxylic Acid Derivatives | |
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| Reactions of Carboxylic Acid Derivatives with Organometallic Reagents | |
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| Synthesis of Carboxylic Acid Derivatives | |
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| Use and Occurrence of Carboxylic Acids and Their Derivatives | |
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| Key Ideas in Chapter 21 | |
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| Additional Problems | |
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| Chemistry of Enolate Ions, Enols, and [alpha],[beta]-Unsaturated Carbonyl Compounds | |
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| Acidity of Carbonyl compounds | |
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| Enolization of Carbonyl Compounds | |
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| [alpha]-Halogenation of Carbonyl Compounds | |
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| Aldol Addition and Aldol Condensation | |
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| Condensation Reactions Involving Ester Enolate Ions | |
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| Biosynthesis of Fatty Acids | |
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| Alkylation of Ester Enolate Ions | |
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| Conjugate-Addition Reactions | |
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| Reduction of [alpha],[beta]-Unsaturated Carbonyl Compounds | |
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| Reactions of [alpha],[beta]-Unsaturated Carbonyl Compounds with Organometallic Reagents | |
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| Organic Synthesis with Conjugate-Addition Reactions | |
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| Key Ideas in Chapter 22 | |
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| Additional Problems | |
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| Chemistry of Amines | |
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| Nomenclature of Amines | |
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| Structure of Amines | |
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| Physical Properties of Amines | |
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| Spectroscopy of Amines | |
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| Basicity and Acidity of Amines | |
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| Quaternary Ammonium Salts | |
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| Alkylation and Acylation Reactions of Amines | |
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| Hofmann Elimination of Quaternary Ammonium Hydroxides | |
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| Aromatic Substitution Reactions of Aniline Derivatives | |
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| Diazotization: Reactions of Diazonium Ions | |
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| Synthesis of Amines | |
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| Use and Occurrence of Amines | |
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| Key Ideas in Chapter 23 | |
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| Additional Problems | |
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| Chemistry of Naphthalene and the Aromatic Heterocycles | |
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| Chemistry of Naphthalene | |
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| Introduction to the Aromatic Heterocycles | |
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| Chemistry of Furan, Pyrrole, and Thiophene | |
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| Synthesis of Indoles | |
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| Chemistry of Pyridine and Quinoline | |
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| Occurrence of Heterocyclic Compounds | |
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| Key Ideas in Chapter 24 | |
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| Additional Problems | |
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| Pericyclic Reactions | |
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| Molecular Orbitals of Conjugated [pi]-Electron Systems | |
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| Electrocyclic Reactions | |
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| Cycloaddition Reactions | |
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| Sigmatropic Reactions | |
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| Summary of the Pericyclic Selection Rules | |
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| Fluxional Molecules | |
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| Formation of Vitamin D | |
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| Key Ideas in Chapter 25 | |
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| Additional Problems | |
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| Amino Acids, Peptides, and Proteins | |
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| Nomenclature of Amino Acids and Peptides | |
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| Stereochemistry of the [alpha]-Amino Acids | |
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| Acid-Base Properties of Amino Acids and Peptides | |
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| Synthesis and Enantiomeric Resolution of [alpha]-Amino Acids | |
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| Acylation and Esterification Reactions of Amino Acids | |
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| Determination of Peptide Structure | |
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| Solid-Phase Peptide Synthesis | |
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| Combinatorial Chemistry | |
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| Structures of Peptides and Proteins | |
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| Enzymes: Biological Catalysts | |
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| Occurrence of Peptides and Proteins | |
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| Key Ideas in Chapter 26 | |
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| Additional Problems | |
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| Carbohydrates and Nucleic Acids | |
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| Classification and Properties of Carbohydrates | |
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| Structures of the Monosaccharides | |
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| Mutarotation of Carbohydrates | |
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| Base-Catalyzed Isomerization of Aldoses and Ketoses | |
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| Glycosides | |
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| Ether and Ester Derivatives of Carbohydrates | |
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| Oxidation and Reduction Reactions of Carbohydrates | |
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| Kiliani-Fischer Synthesis | |
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| Proof of Glucose Stereochemistry | |
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| Disaccharides and Polysaccharides | |
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| Nucleosides, Nucleotides, and Nucleic Acids | |
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| DNA, RNA, and the Genetic Code | |
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| Key Ideas in Chapter 27 | |
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| Additional Problems | |
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| Appendixes | |
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| Substitutive Nomenclature of Organic Compounds | |
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| Infrared Absorptions of Organic Compounds | |
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| Proton NMR Chemical Shifts in Organic Compounds | |
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| [superscript 13]C NMR Chemical Shifts in Organic Compounds | |
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| Summary of Synthetic Methods | |
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| Reactions Used to Form Carbon-Carbon Bonds | |
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| Typical Acidities and Basicities of Organic Functional Groups | |
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| Credits | |
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| Index | |