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| Preface | |
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| Preface to the First Edition | |
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| Functional Groups and Chemical Bonding | |
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| Functional Groups | |
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| Orbitals | |
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| Bonding Schemes | |
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| Antibonding Orbitals | |
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| Resonance | |
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| Conjugated [pi] Systems | |
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| Aromaticity | |
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| Bibliography | |
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| Problems | |
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| Oxidation States of Organic Compounds | |
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| Oxidation Levels | |
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| Oxidation States in Alkanes | |
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| Oxidation States in Alkenes | |
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| Oxidation States in Common Functional Groups | |
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| Oxidation Level Changes During Reactions | |
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| Bibliography | |
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| Problems | |
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| Acidity and Basicity | |
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| Bronsted and Lewis Acids and Bases | |
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| Acid Strength | |
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| Acid-Base Equilibria | |
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| Amphoteric Compounds | |
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| Structural Effects on Acidity | |
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| Electronegativity | |
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| Inductive Effects | |
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| Resonance Effects | |
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| Bibliography | |
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| Problems | |
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| Curved-Arrow Notation | |
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| Electron Movement | |
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| Heterolytic Bond Cleavages | |
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| Heterolytic Bond Formation | |
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| Homolytic Bond Making and Bond Breaking | |
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| Resonance Structures | |
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| Depiction of Mechanism | |
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| Bibliography | |
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| Problems | |
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| Mechanisms of Organic Reactions | |
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| Activation Energy | |
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| Activated Complex | |
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| Reaction Energetics | |
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| Structure of the Activated Complex | |
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| Hammond Postulate | |
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| Reaction Kinetics | |
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| Determining Activation Energies | |
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| Isotope Effects | |
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| Electronic Effects | |
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| Hammett Equation | |
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| Bibliography | |
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| Problems | |
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| Stereochemical and Conformational Isomerism | |
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| Stereochemical Structures | |
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| Chirality | |
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| Configuration of Chiral Centers | |
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| Multiple Stereocenters | |
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| Optical Activity | |
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| Absolute Configuration | |
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| Physical Properties of Enantiomers | |
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| Resolution of Enantiomers | |
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| Stereoselective Reactions | |
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| Formation of Enantiomers | |
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| Formation of Diastereomers | |
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| Stereochemistry to Deduce Mechanism | |
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| Conformational Analysis | |
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| Conformational Energies | |
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| A Values | |
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| Strain in Ring Systems | |
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| Stereoelectronic Effects | |
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| Bibliography | |
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| Problems | |
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| Functional Group Synthesis | |
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| Functional Group Manipulation | |
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| Carboxylic Acids | |
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| Esters | |
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| Amides | |
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| Acid Chlorides | |
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| Aldehydes | |
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| Ketones | |
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| Imines and Imine Derivatives | |
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| Alcohols | |
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| Amines | |
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| Alkenes | |
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| Alkanes | |
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| Bibliography | |
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| Problems | |
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| Carbon-Carbon Bond Formation between Carbon Nucleophiles and Carbon Electrophiles | |
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| Synthetic Strategy | |
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| Nucleophilic Carbon | |
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| Electrophilic Carbon | |
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| Reactivity Matching | |
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| Generation of Nucleophilic Carbon Reagents | |
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| Generation of Electrophilic Carbon Reagents | |
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| Matching Nucleophiles with Electrophiles | |
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| Enolates | |
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| Enolate Regioisomers | |
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| Diastereoselection in Aldol Reactions | |
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| Organometallic Compounds | |
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| Neutral Carbon Nucleophiles | |
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| C=C Formation | |
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| Cyclopropanation Reactions | |
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| Metal-Catalyzed Carbon--Carbon Bond Formation | |
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| Pd(0)-Catalyzed Carbon--Carbon Bond Formation | |
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| Heck Reaction | |
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| Suzuki Coupling | |
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| Stille Coupling | |
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| Olefin Metathesis | |
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| Bibliography | |
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| Problems | |
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| Carbon--Carbon Bond Formation by Free-Radical Reactions | |
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| Free-Radical Reactions | |
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| Free-Radical Polymerization | |
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| Nonpolymerization Reactions | |
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| Free-Radical Initiation | |
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| Free-Radical Cyclization | |
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| Bibliography | |
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| Problems | |
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| Planning Organic Syntheses | |
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| Retrosynthetic Analysis | |
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| Carbon Skeleton Synthesis | |
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| Umpolung Synthons | |
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| Acetylide Nucleophiles | |
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| Ring Construction | |
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| Robinson Annulation | |
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| Diels--Alder Reaction | |
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| HOMO--LUMO Interactions | |
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| Stereoelectronic Factors | |
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| 1,3-Dipolar Cycloadditions | |
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| Bibliography | |
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| Problems | |
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| Structure Determination of Organic Compounds | |
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| Structure Determination | |
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| Chromatographic Purification | |
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| Instrumental Methods | |
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| Nuclear Magnetic Resonance | |
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| Chemical Shift | |
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| Spin--Spin Coupling | |
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| Descriptions of Spin Systems | |
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| Second-Order Splitting | |
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| Structure Identification by [superscript 1]H NMR | |
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| Carbon-13 NMR | |
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| Infrared Spectroscopy | |
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| IR Stretching Frequencies | |
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| Use of IR Spectroscopy for Structure Determination | |
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| Mass Spectrometry | |
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| Fragmentation Processes | |
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| Bibliography | |
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| Problems | |
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| Solutions to Chapter Problems | |
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| Index | |