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| Preface | |
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| To the Student | |
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| To the Instructor | |
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| Acknowledgments | |
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| The Structures of Organic Molecules | |
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| Structural Components of Organic Molecules | |
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| Structural Formulas and Condensed Structures | |
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| Systematic Nomenclature: IUPAC Names | |
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| Constitutional Isomers and Hydrocarbon Substituents | |
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| Naming Organic Compounds | |
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| Chapter Summary | |
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| Bonding in Organic Molecules | |
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| Lewis Structures | |
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| Bond Properties | |
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| Resonance Structures | |
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| The Formation of Bonds | |
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| Hybrid Orbitals and Shapes of Molecules | |
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| Bonus with Herteroatoms | |
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| Delocauzed 71 Electron Systems | |
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| Noncovalent Interactions | |
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| Chapter Summary | |
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| The Conformations of Organic Molecules | |
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| Conformations of Acyclic Compounds | |
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| Conformations of Cyclic Compounds | |
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| Conformations of Substituted Cyclohexanes | |
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| Conformations of Other Cyclic Compounds | |
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| Chapter Summary | |
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| The Stereochemistry of Organic Molecules | |
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| Geometric Isomers of Alkenes | |
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| Chirality and Enantiomers | |
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| Diastereomers | |
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| Fischer Projections | |
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| Reaction Stereochemistry: A Preview | |
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| Chapter Summary | |
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| Chemical Reactions and Mechanisms | |
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| General Aspects of Reactions | |
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| Acid-Base Reactions | |
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| Reaction Mechanisms | |
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| Reaction Coordinate Diagrams | |
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| Reactions in Biological Systems | |
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| Chapter Summary | |
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| Substitution Reactions of Alkyl Halides | |
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| Fundamental Aspects of Substitution Reactions | |
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| The SN1 Reaction of Alkyl Halides | |
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| The SN2 Reaction of Alkyl Halides | |
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| A Comparison of the SN1 and SN2 Mechanisms | |
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| Chapter Summary | |
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| Substitution Reactions of Alcohols and Related Compounds | |
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| Substitution Reactions of Alcohols | |
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| Substitution Reactions of Ethers and Epoxides | |
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| Substitution Reactions of Thiols and Thioethers | |
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| Substitution Reactions in Biochemical Systems | |
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| Chapter Summary | |
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| Elimination Reactions of Alkyl Halides, Alcohols, and Related Compounds | |
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| The E1 Reaction | |
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| The E2 Reaction | |
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| Substitution Versus Elimination | |
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| Elimination Reactions in Biology | |
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| Chapter Summary | |
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| Addition Reactions of Alkenes and Alkynes | |
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| Electrophilic Addition Reactions of Alkenes | |
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| Electrophilic Addition Reactions of Alkynes | |
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| The Formation of Carbon-Carbon Bonds | |
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| Hydroboration Reactions of [Pi] Bonds | |
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| The Addition of Carbenes to [Pi] Bonds | |
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| Chapter Summary | |
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| Addition Reactions of Conjugated Dienes | |
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| The Structures of Dienes | |
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| Bonding in Conjugated Dienes | |
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| Electrophilic Addition to Conjugated Dienes | |
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| The Diels-Alder Reaction | |
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| Chapter Summary | |
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| Oxidation and Reduction Reactions | |
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| Oxidation States in Organic Molecules | |
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| Hydrogenation Reactions | |
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| Oxidation Reactions of Alkenes | |
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| Oxidation Reactions of Alcohols | |
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| Oxidation Reactions of Amines | |
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| Chapter Summary | |
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| Free Radical Reactions | |
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| Free Radical Halogenation Reactions | |
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| Reduction via Radical Intermediates | |
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| Free Radical Addition Reactions | |
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| Oxidation via Radical Intermediates | |
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| Chapter Summary | |
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| Proton and Carbon NMR Spectroscopy | |
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| Chemical Shifts and Proton Equivalence | |
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| Spin Coupling in Simple Systems | |
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| Interpreting and Predicting 1h NMR Spectra | |
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| Spin Coupling in More Complex Systems | |
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| Carbon NMR Spectra | |
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| Interpreting 13C NMR Spectra | |
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| Chapter Summary | |
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| Determining the Structures of Organic Molecules | |
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| Analytical Data in Structure Determinations | |
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| Mass Spectrometry | |
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| Infrared Spectroscopy | |
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| Combined Structure Determination Exercises | |
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| Chapter Summary | |
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| Organometallic Reagents and Chemical Synthesis | |
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| Carbon-Carbon Bond Formation | |
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| Organomagnesium and Lithium Compounds | |
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| Transition Metal Organometallic Compounds | |
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| Retrosynthesis | |
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| Selectivity Criteria in Synthesis | |
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| Chapter Summary | |
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| Asymmetric Reactions and Synthesis | |
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| Chiral Compounds | |
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| Enantiomeric Resolution | |
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| Asymmetric Synthesis | |
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| Enantioselective Addition Reactions | |
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| Synthetic Design of Chiral Molecules | |
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| Chapter Summary | |
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| The Chemistry of Benzene and Its Derivatives | |
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| Structural Aspects of Aromatic Molecules | |
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| Electrophilic Substitution Reactions of Benzene | |
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| Electrophilic Substitution Reactions of Benzene Derivatives | |
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| Other Reactions of Benzene and Its Derivatives | |
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| Chapter Summary | |
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| Nucleophilic Addition Reactions of Aldehydes and Ketones | |
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| General Aspects of Nucleophilic Addition Reactions | |
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| Nucleophilic Addition Reactions | |
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| Reduction Reactions of Aldehydes and Ketones | |
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| Oxidation Reactions of Aldehydes and Ketones | |
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| Chapter Summary | |
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| Addition-Substitution Reactions of Aldehydes and Ketones: Carbohydrate Chemistry | |
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| Hemiacetals and Acetals | |
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| Acetals as Protecting Groups | |
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| Carbohydrates | |
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| Glycosides | |
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| Oxidation and Reduction Reactions of Carbohydrates | |
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| Chapter Summary | |
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| Addition-Elimination Reactions of Aldehydes and Ketones | |
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| Compounds with Carbon-Nitrogen Double Bonds | |
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| Imine Chemistry and Biochemistry | |
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| Enamines | |
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| Ylides | |
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| Chapter Summary | |
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| Addition-Elimination Reactions of Carboxylic Acids and Derivatives | |
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| General Aspects of Structure and Reactivity | |
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| Reactions of Carboxylic Acids | |
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| The Chemistry of Acid Chlorides, Thioesters, and Anhydrides | |
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| The Chemistry of Esters | |
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| The Chemistry of Amides | |
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| The Chemistry of Nitriles | |
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| Reactions with Organometallic Compounds | |
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| Reduction Reactions of Carboxylic Acids and Derivatives | |
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| Chapter Summary | |
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| The Acid-Base Chemistry of Carbonyl Compounds | |
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| Acidity of Carbonyl Compounds | |
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| Enols and Enolate Ions | |
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| Reactions of Enolate Ions | |
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| Dicarbonyl Compounds | |
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| Reactions of Amide and Imide Ions | |
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| Chapter Summary | |
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| The Nucleophilic Addition Reactions of Enolate Ions | |
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| The Aldol Reaction | |
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| Crossed-Aldol Reactions | |
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| The Claisen Condensation | |
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| Crossed-Claisen Condensations | |
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| Chapter Summary | |
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| Conjugate Addition Reactions of Unsaturated Carbonyl Compounds | |
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| [alpha],[Beta]-Unsaturated Carbonyl Compounds | |
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| Conjugate Addition Reactions | |
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| Conjugate Addition Reactions of Carbanions | |
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| Reduction Reactions | |
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| Chapter Summary | |
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| The Chemistry of Polycyclic and Heterocyclic Arenes | |
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| Polycyclic Aromatic Compounds | |
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| Pyridine and Related Heterocycles | |
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| Pyrrole and Related Heterocycles | |
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| Azoles | |
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| Chapter Summary | |
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| Polymers and Polymerization | |
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| Polymers and Their Properties | |
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| Chain-Growth Polymerization | |
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| Step-Growth Polymerization | |
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| Modification of Polymers | |
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| Chapter Summary | |
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| Amino Acids, Peptides, and Proteins | |
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| Amino Acids | |
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| Chemical Synthesis of Amino Acids | |
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| Asymmetric Synthesis of Amino Acids | |
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| Peptide Synthesis and Analysis | |
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| Protein Structures | |
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| Chapter Summary | |
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| Nucleic Acids and Molecular Recognition | |
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| Nucleosides and Nucleotides | |
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| Nucleic Acid Structures | |
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| Molecular Recognition | |
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| Crown Ethers and Cryptands | |
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| Cavity-Containing Molecules | |
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| Recognition Using Hydrogen Bonds | |
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| Chapter Summary | |
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| Appendix | |
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| Glossary | |
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| Index | |