Preface xxii
  1 Introduction and Review
  2 Structure and Properties of Organic Molecules
  3 Structure and Stereochemistry of Alkanes
  4 The Study of Chemical Reactions
  5 Stereochemistry
  6 Alkyl Halides: Nucleophilic Substitution and Elimination
  7 Structure and Synthesis of Alkenes
  8 Reactions of Alkenes
  9 Alkynes
  10 Structure and Synthesis of Alcohols
  11 Reactions of Alcohols
  12 Infrared Spectroscopy and Mass Spectrometry
  13 Nuclear Magnetic Resonance Spectroscopy
  14 Ethers, Epoxides, and Sulfides
  15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
  16 Aromatic Compounds
  17 Reactions of Aromatic Compounds
  18 Ketones and Aldehydes
  19 Amines
  20 Carboxylic Acids
  21 Carboxylic Acid Derivatives
  22 Alpha Substitutions and Condensations of Enols and Enolate Ions
  23 Carbohydrates and Nucleic Acids
  24 Amino Acids, Peptides, and Proteins
  25 Lipids
  26 Synthetic Polymers
   Appendices
   Answers to Selected Problems
   Photo Credits PC1
   IndexI1
  Preface xxii
  About the Author xxxviii
  Chapter 1
  Introduction and Review
   1-1 The Origins of Organic Chemistry
   1-2 Principles of Atomic Structure
   1-3 Bond Formation: The Octet Rule
   I-4 Lewis Structures
   1-5 Multiple Bonding
   Summary: Common Bonding Patterns (Uncharged)
   1-6 Electronegativity and Bond Polarity
   1-7 Formal Charges
   1-8 Ionic Structures
   Summary: Common Bonding Patterns in Organic Compounds and Ions
   1-9 Resonance
   1-10 Structural Formulas
   1-11 Molecular Formulas and Empirical Formulas
   1-12 Arrhenius Acids and Bases
   1-13 Brφnsted-Lowry Acids and Bases
   1-14 Lewis Acids and Bases
   Chapter 1 Glossary
   Study Problems
  Chapter 2
  Structure and Properties of Organic Molecules
   2-1 Wave Properties of Electrons in Orbitals
   2-2 Molecular Orbitals
   2-3 PiBonding
   2-4 Hybridization and Molecular Shapes
   2-5 Drawing Three-Dimensional Molecules
   2-6 General Rules of Hybridization and Geometry
   2-7 Bond Rotation
   2-8 Isomerism
   2-9 Polarity of Bonds and Molecules
   2-10 Intermolecular Attractions and Repulsions
   2-11 Polarity Effects on Solubilities
   2-12 Hydrocarbons
   2-13 Organic Compounds Containing Oxygen
   2-14 Organic Compounds Containing Nitrogen
   Chapter 2 Glossary
   Study Problems
  Chapter 3
  Structure and Stereochemistry of Alkanes
   3-1 Classification of Hydrocarbons (Review)
   3-2 Molecular Formulas of Alkanes
   3-3 Nomenclature of Alkanes Summary: Rules for Naming Alkanes
   3-4 Physical Properties of Alkanes
   3-5 Uses and Sources of Alkanes
   3-6 Reactions of Alkanes
   3-7 Structure and Conformations of Alkanes
   3-8 Conformations of Butane
   3-9 Conformations of Higher Alkanes
   3-10 Cycloalkanes
   3-11 cis-trans Isomerism in Cycloalkanes
   3-12 Stabilities of Cycloalkanes; Ring Strain
   3-13 Cyclohexane Conformations Problem-Solving Strategy: Drawing Chair Conformations
   3-14 Conformations of Monosubstttuted Cyclohexanes
   3-15 Conformations of Disubstituted Cyclohexanes Problem-Solving Strategy: Recognizing cis and trans Isomers
   3-16 Bicyclic Molecules Chapter 3 Glossary Study Problems
  Chapter 4
  The Study of Chemical Reactions
   4-1 Introduction
   4-2 Chlorination of Methane
   4-3 The Free-Radical Chain Reaction
   KEY MECHANISM: Free-Radical Halogenation
   4-4 Equilibrium Constants and Free Energy
   4-5 Enthalpy and Entropy
   4-6 Bond-Dissociation Energies
   4-7 Enthalpy Changes in Chlorination
   4-8 Kinetics and the Rate Equation
   4-9 Activation Energy and the Temperature Dependence of Rates
   4-10 Transition States
   4-11 Rates of Multistep Reactions
   4-12 Temperature Dependence of Halogenation
   4-13 Halogenation of Higher Alkanes
   4-14 The Hammond Postulate
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   4-15 Radical Inhibitors
   4-16 Reactive Intermediates
   Summary: Reactive Intermediates
   Chapter 4 Glossary
   Study Problems
  Chapter 5
  Stereochemistry
   5-1 Introduction
   5-2 Chirality
   5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms
   5-4 Optical Activity
   5-5 Biological Discrimination of Enantiomers
   5-6 Racemic Mixtures
   5-7 Enantiomeric Excess and Optical Purity
   5-8 Chirality of Conformationally Mobile Systems
   5-9 Chiral Compounds without Asymmetric Atoms
   5-10 Fischer Projections
   Summary: Fischer Projections and Their Use
   5-11 Diastereomers
   Summary:Types of Isomers
   5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons
   5-13 Meso Compounds
   5-14 Absolute and Relative Configuration
   5-15 Physical Properties of Diastereomers
   5-16 Resolution of Enantiomers
   Chapter 5 Glossary
   Study Problems
  Chapter 6
  Alkyl Halides: Nucleophilic Substitution and Elimination
   6-1 Introduction
   6-2 Nomenclature of Alkyl Halides
   6-3 Common Uses of Alkyl Halides
   6-4 Structure of Alkyl Halides
   6-5 Physical Properties of Alkyl Halides
   6-6 Preparation of Alkyl Halides
   Summary: Methods for Preparing Alkyl Halides
   6-7 Reactions of Alkyl Halides: Substitution and Elimination
   6-8 Second-Order Nucleophilic Substitution: The SN2 Reaction
   KEY MECHANISM: The SN2 Reaction
   6-9 Generality of the SN2 Reaction
   Summary: SN2 Reactions of Alkyl Halides
   6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
   Summary: Trends in Nucleophilicity
   6-11 Reactivity of the Substrate in SN2 Reactions
   6-12 Stereochemistry of the SN2 Reaction
   6-13 First-Order Nucleophilic Substitution: The SN1 Reaction
   KEY MECHANISM: The SO Reaction
   6-14 Stereochemistry of the SN1 Reaction
   6-15 Rearrangements in SN1 Reactions
   6-16 Comparison of SNI and SN2 Reactions
   Summary: Nucleophilic Substitutions
   6-17 First-Order Elimination: The El Reaction
   KEY MECHANISM: The E1 Reaction
   Summary: Carbocation Reactions
   6-18 Second-Order Elimination: The E2 Reaction
   KEY MECHANISM: The E2 Reaction
   6-19 Positional Orientation of Elimination: The Saytzeff Rule
   6-20 Stereochemistry of the E2 Reaction
   6-21 Comparison of E1 and E2 Elimination Mechanisms
   Summary: Elimination Reactions
   Problem-Solving Strategy: Predicting Substitutions and Eliminations
   Summary: Reactions of Alkyl Halides
   Chapter 6 Glossary
   Study Problems
  Chapter 7
  Structure and Synthesis of Alkenes
   7-1 Introduction
   7-2 The Orbital Description of the Alkene Double Bond
   7.3Elements of Unsaturauon
   7-4 Nomenctature of Alkenes
   7-5 Nomenctature of Cis-trans Isomers
   Summary: Ruies for Naming Alkenes
   7-6 Commercial Importance of Alkenes
   7-7 Stability of ACKenes
   7-8Physical Properties of Alkenes
   7-9 Alkene Synthesis by Elimination of Alkyl Halides
   7-10 Alkene Synthesis by Dehydration of Alcohols
   KEY MECHANISM: Acid-Catalyzed Dehydration of an Alcohol
   7-11 Alkene Syntnesis by High-Temperature Industrial Methods
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   Summary: Methods for Synthesis of Alkenes
   Chapter 7 Glossary
   Study Problems
  Chapter 8
  Reactions of Alkenes
   8-1 Reactivity of the Carbon-Carbon Double Bond
   8-2 Electrophilic Addition to Alkenes
   KEY MECHANISM: Electrophilic Addition to Alkenes
   8-3 Addition of Hydrogen Halides to Alkenes
   8-4 Addition of Water: Hydration of Alkenes
   8-5 Hydration by Oxymercuration-Demercuration
   8-6 Alkoxymercuration-Demercuration
   8-7 Hydroboration of Alkenes
   8-8 Catalytic Hydrogenation of Alkenes
   8-9 Addition of Carbenes to Alkenes
   8-10 Addition of Halogens to Alkenes
   8-11 Formation of Halohydrins
   8-12 Epoxidation of Alkenes
   8-13 Acid-Catalyzed Opening of Epoxides
   8-14 Syn Hydroxylation of Alkenes
   8-15 Oxidative Cleavage of Alkenes
   8-16 Polymerization of Alkenes
   Problem-Solving Strategy: Organic Synthesis
   Summary: Reactions of Alkenes
   Chapter 8 Glossary
   Study Problems
  Chapter 9
  Alkynes
   9-1 Introduction
   9-2 Nomenclature of Alkynes
   9-3 Physical Properties of Alkynes
   9-4 Commercial Importance of Alkynes
   9-5 Electronic Structure of Alkynes
   9-6 Acidity of Alkynes
   9-7 Synthesis of Alkynes from Acetylides
   9-8 Synthesis of Alkynes by Elimination Reactions
   Summary: Syntheses of Alkynes
   9-9 Addition Reactions of Alkynes
   9-10 Oxidation of Alkynes
   Problem-Solving Strategy: Multistep Synthesis
   Summary: Reactions of Alkynes
   Chapter 9 Glossary
   Study Problems
  Chapter 10
  Structure and Synthesis of Alcohols
   10-1 Introduction
   10-2 Structure and Classification of Alcohols
   10-3 Nomenclature of Alcohols and Phenols
   10-4 Physical Properties of Alcohols
   10-5 Commercially Important Alcohols
   10-6 Acidity of Alcohols and Phenols
   10-7 Synthesis of Alcohols: Introduction and Review
   Summary: Previous Alcohol Syntheses
   10-8 Organometallic Reagents for Alcohol Synthesis
   10-9 Addition of Organometallic Reagents to Carbonyl Compounds
   KEY MECHANISM: Grignard Reactions
   Summary: Grignard Reactions
   10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
   10-11 Reduction of the Carbonyl Group: Synthesis of 1°and 2°Alcohols
   Summary: Reactions of LiAIH4 and NaBH4
   Summary: Alcohol Syntheses
   10-12 Thiols (Mercaptans)
   Chapter 10 Glossary
   Study Problems
  Chapter 11
  Reactions of Alcohols
   11-1 Oxidation States of Alcohols and Related Functional Groups
   11-2 Oxidation of Alcohols
   11-3 Additional Methods for Oxidizing Alcohols
   1l-4 Biological Oxidation of Alcohols
   11-5 Alcohols as Nucleophiles and Electrophiles; Formation of iosyiates
   Summary: SN2 Reactions of Tosylate Esters
   11-6 Reduction of Alcohols
   11-7 Reactions of Alcohols with Hydrohalic Acids
   11-8 Reactions of Alcohols with Phosphorus Halides
   11-9 Reactions of Alcohols with Thionyl Chloride
   11-10 Dehydration Reactions of Alcohols
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   11-11 Unique Reactions of Diols
   11-12 Esterification of Alcohols
   11-13 Esters of Inorganic Acids
   11-14 Reactions of Alkoxides
   KEY MECHANISM: The Williamson Ether Synthesis
   Problem-Solving Strategy: Multistep Synthesis
   Summary: Reactions of Alcohols
   Chapter 11 Glossary
   Study Problems
  Chapter 12
  Infrared Spectroscopy and mass Spectrometry
   12-1 Introduction
   12-2 The Electromagnetic Spectrum
   12-3 The Infrared Region
   12-4 Molecular Vibrations
   12-5 IR-Active and IR-Inactive Vibrations
   12-6 Measurement of the IR Spectrum
   12-7 Infrared Spectroscopy of Hydrocarbons
   12-8 Characteristic Absorptions of Alcohols and Amines
   12-9 Characteristic Absorptions of Carbonyl Compounds
   12-10 Characteristic Absorptions of C—N Bonds
   12-11 Simplified Summary of IR Stretching Frequencies
   12-12 Reading and Interpreting IR Spectra (Solved Problems)
   12-13 Introduction to Mass Spectrometry
   12-14 Determination of the Molecular Formula by Mass Spectrometry
   12-15 Fragmentation Patterns in Mass Spectrometry
   Summary: Common Fragmentation Patterns
   Chapter 12 Glossary
   Study Problems
  Chapter 13
  Nuclear Magnetic Resonance Spectroscopy
   13-1 Introduction
   13-2 Theory of Nuclear Magnetic Resonance
   13-3 Magnetic Shielding by Electrons
   13-4 The NMR Spectrometer
   13-5 The Chemical Shift
   13-6 The Number of Signals
   13-7 Areas of the Peaks
   13-8 Spin-Spin Splitting
   Problem-Solving Strategy: Drawing an NMR Spectrum
   13-9 Complex Splitting
   13-10 Stereochemical Nonequivalence of Protons
   13-11 Time Dependence of NMR Spectroscopy
   Problem-Solving Strategy: Interpreting Proton NMR Spectra
   13-12 Carbon-13 NMR Spectroscopy
   13-13 Interpreting Carbon NMR Spectra
   13-14 Nuclear Magnetic Resonance Imaging
   Problem-Solving Strategy: Spectroscopy Problems
   Chapter 13 Glossary
   Study Problems
  Chapter 14
  Ethers, Epoxides, and Sulfides
   14-1 Introduction
   14-2 Physical Properties of Ethers
   14-3 Nomenclature of Ethers
   14-4 Spectroscopy of Ethers
   14-5 The Williamson Ether Synthesis
   14-6 Synthesis of Ethers by Alkoxymercuration-Demercuration
   14-7 Industrial Synthesis: Bimolecular Dehydration of Alcohols
   Summary: Syntheses of Ethers
   14-8 Cleavage of Ethers by HBr and HI
   14-9 Autoxidation of Ethers
   Summary: Reactions of Ethers
   14-10 Sulfides (Thioethers)
   14-11 Synthesis of Epoxides
   Summary: Epoxide Syntheses
   14-12 Acid-Catalyzed Ring Opening of Epoxides
   14-13 Base-Catalyzed Ring Opening of Epoxides
   14-14 Orientation of Epoxide Ring Opening
   14-15 Reactions of Epoxides with Grignard and Organolithium Reagents
   14-16 Epoxy Resins: The Advent of Modern Glues
   Summary: Reactions of Epoxides
   Chapter 14 Glossary
   Study Problems
  Chapter 15
  Conjugated Systems, Orbital Symmetry,and Ultraviolet Spectroscopy
   15-1 Introduction
   15-2 Stabilities of Dienes
   15-3 Molecular Orbital Picture of a Conjugated System
   15-4 Allylic Cations
   15-5 1,2-and 1,4-Addition to Conjugated Dienes
   15-6 Kinetic versus Thermodynamic Control in the Addition of HBr to 1,3-Butadiene
   15-7 Allylic Radicals
   15-8 Molecular Orbitals of the Allylic System
   15-9 Electronic Configurations of the Allyl Radical, Cation, and Anion
   15-10 SN2 Displacement Reactions of Allylic Halides and Tosylates
   15-11 The Diels-Alder Reaction
   KEY MECHANISM: The Diels-Alder Reaction
   15-12 The Diels-Alder as an Example of a Pericyclic Reaction
   15-13 Ultraviolet Absorption Spectroscopy
   Chapter 15 Glossary
   Study Problems
  Chapter 16
  Aromatic Compounds
   16-1 Introduction: The Discovery of Benzene
   16-2 The Structure and Properties of Benzene
   16-3 The Molecular Orbitals of Benzene
   16-4 The Molecular Orbital Picture of Cyclobutadiene
   16-5 Aromatic, Antiaromatic, and Nonaromatic Compounds
   16-6 Hǖckel’s Rule
   16-7 Molecular Orbital Derivation of Hǖckel’s Rule
   16-8 Aromatic Ions
   16-9 Heterocyclic Aromatic Compounds
   16-10 Polynuclear Aromatic Hydrocarbons
   16-11 Aromatic Allotropes of Carbon
   16-12 Fused Heterocyclic Compounds
   16-13 Nomenclature of Benzene Derivatives
   16-14 Physical Properties of Benzene and Its Derivatives
   16-15 Spectroscopy of Aromatic Compounds
   Chapter 16 Glossary
   Study Problems
  Chapter 17
  Reactions of Aromatic Compounds
   17-1 ElectroDhilicAromatic Substitution
   KEY MECHANISM: Electrophilic Aromatic 5utistitutlon
   17-2 Halogenation of Benzene
   17-3 Nitration of Benzene
   17-4 Sulfonation of Benzene
   17-5 Nitration of Toluene: The Effect of Alky1 Substitution
   17-6 Activating, Ortho, Para-Directing Substituents
   Summary: Activating, Ortho, Para-Directors
   17-7 Deactivating, Meta-Directing Substituents
   Summary: Deactivatine, Meta-Directors
   17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
   Summary: Directnp Effects of Substituents
   17-9 Effects of Multiple Substituents on Electrophthc Aromatic Sutistituaon
   17-10 The Friedel-Crafts Alkylation
   17-11 The Friedel-Crafts Acylation
   Summary: Comparison of Friedel-Crafts Alkylation and Acylation
   17-12 Nucleophilic Aromatic Substitution
   17-13 Addition Reactions of Benzene Denvatives
   17-14 Side-Chain Reactions of Benzene Derivatives
   17-15 Reactions of Phenols
   Summary: Reactions of Aromatic Compounds
   Chapter 17 Glossary
   Studv Problems
  Chapter 18
  Ketones and Aldehydes
   18-1 Carbonyl Compounds
   18-2 Structure of the Carbonyl Group
   18-3 Nomenclature of Ketones and Aldehydes
   18-4 Physical Properties of Ketones and Aldehydes
   18-5 Spectroscopy of Ketones and Aldehydes
   18-6 Industrial Importance of Ketones and Aldehydes
   18-7 Review of Syntheses of Ketones and Aldehydes
   18-8 Synthesis of Ketones and Aldehydes Using 1,3-Dithianes
   18-9 Synthesis of Ketones from Carboxylic Acids
   18-10 Synthesis of Ketones from Nitriles
   18-11 Synthesis of Aldehydes and Ketones from Acid Chlorides
   Summary: Syntheses of Ketones and Aldehydes
   18-12 Reactions of Ketones and Aldehydes: Nucleophilic Addition
   KEY MECHANISM: Nucleophilic Additions to Carbonyl Groups
   18-13 The Wittig Reaction
   18-14 Hydration of Ketones and Aldehydes
   18-15 Formation of Cyanohydrins
   18-16 Formation of Imines
   KEY MECHANISM: Formation of Imines
   18-17 Condensations with Hydroxylamine and Hydrazines
   Summary: Condensations of Amines with Ketones and Aldehydes
   18-18 Formation of Acetals
   KEY MECHANISM: Formation of Acetals
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   18-19 Use of Acetals as Protecting Groups
   18-20 Oxidation of Aldehydes
   18-21 Other Reductions of Ketones and Aldehydes
   Summary: Reactions of Ketones and Aldehydes
   Chapter 18 Glossary
   Study Problems
  Chapter 19
  Amines
   19-1 Introduction
   19-2 Nomenclature of Amines
   19-3 Structure of Amines
   19-4 Physical Properties of Amines
   19-5 Basicity of Amines
   19-6 Effects on Amine Basicity
   19-7 Salts of Amines
   19-8 Amine Salts as Phase-Transfer Catalysts
   19-9 Spectroscopy of Amines
   19-10 Reactions of Amines with Ketones and Aldehydes (Review)
   19-11 Aromatic Substitution of Arylamines and Pyridine (Review)
   19-12 Alkylation of Amines by Alkyl Halides
   19-13 Acylation of Amines by Acid Chlorides
   19-14 Formation of Sulfonamides
   19-15 Amines as Leaving Groups: The Hofmann Elimination
   19-16 Oxidation of Amines; The Cope Elimination
   19-17 Reactions of Amines with Nitrous Acid
   19-18 Reactions of Arenediazonium Salts
   Summary: Reactions of Amines
   19-19 Synthesis of Amines
   Summary: Synthesis of Amines
   Chapter 19 Glossary
   Study Problems
  Chapter 20
  Carboxylic Acids
   20-1 Introduction
   20-2 Nomenclature of Carboxy11c Acias
   20-3 Structure and Physical Properties of Uarboxy11c AC1as
   20-4 Acidity of Carboxylic Acids
   20-5 Salts of Carboxylic Acids
   20-6 Commercial Sources of Carboxylic Acids
   20-7 Spectroscopy of Carboxylic Acids
   20-8 Synthesis of Carboxylic Acids
   Summary: Syntheses of Carboxylic Acids
   20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution
   20-10 Condensation of Acids with Alcohols: The Fischer Esterification
   KEY MECHANISM: Fischer Esterification
   20-11 Synthesis and Use of Acid Chlorides
   20-12 Esterification Using Diazomethane
   20-13 Condensation of Acids with Amines: Direct Synthesis of Amides
   20-14 Reduction of Carboxylic Acids
   20-15 Alkylation of Carboxylic Acids to Form Ketones
   Summary: Reactions of Carboxylic Acids
   Chapter 20 Glossary
   Study Problems
  Chapter 21
  Carboxylic Acid Derivatives
   21-1 Introduction
   21-2 Structure and Nomenclature of Acid Derivatives
   21-3 Physical Properties of Carboxylic Acid Derivatives
   21-4 Snectroscoov of Carboxylic Acid Derivatives
   21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
   KEY MECHANISM: Addition-Elimination Mechanism of Nucleophilic Acyl
   substitution
   21-6 Acid-Catalyzed Nucleophilic Acyl Substitution
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   21-7 Hydrolysis of Carboxylic Acid Derivatives
   21-8 Reduction of Acid Derivatives
   21-9 Reactions of Acid Derivatives with Organometallic Reaeents
   21-10 summary or the unerrustry of Acrd Chlorides
   21-11 Summary of the Chemistry of Anhydrides
   21-12 Summary of the Chemistry of Esters
   21-13 Summary of the Chemistry of Amides
   21-14 Summary of the Chemistry of Nitriles
   21-15 Thioesters
   21-16 Esters and Amides of Carbonic Acid
   Chapter 21 Glossary
   Study Problems
  Chapter 22
  Alpha Substitutions and Condensations of Enols and Enolate Ions
   22-1 Introduction
   22-2 Enols and Enolate Ions
   22-3 Alpha Halogenation of Ketones
   22-4 a Bromination of Acids: The HVZ Reaction
   22-5 Alkylation of Enolate Ions
   22-6 Formation and Alkylation of Enamines
   22-7 The Aldol Condensation of Ketones and Aldehydes
   KEY MECHANISM: Base-Catalyzed Aldol Condensation
   22-8 Dehydration of Aldol Products
   KEY MECHANISM: Dehydration of an Aldol
   22-9 Crossed Aldol Condensations
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   22-10 Aldol Cyclizations
   22-11 Planning Syntheses Using Aldol Condensations
   22-12 The Claisen Ester Condensation
   KEY MECHANISM: Claisen Condensation
   22-13 The Dieckmann Condensation: A Claisen Cyclization
   22-14 Crossed Claisen Condensations
   22-15 Syntheses Using β-Dicarbonyl Compounds
   22-16 The Malonic Ester Synthesis
   22-17 The Acetoacetic Ester Synthesis
   22-18 Conjugate Additions: The Michael Reaction
   KEY MECHANISM: 1,2-Addition and 1,4-Addition
   22-19 The Robinson Annulation
   Problem-Solving Strategy: Proposing Reaction Mechanisms
   Summary:Enolate Additions and Condensations
   Chapter 22 Glossary
   Study Problems
  Chapter 23
  Carbohydrates and Nucleic Acids
   23-1 Introduction
   23-2 Classification of Carbohydrates
   23-3 Monosaccharides
   23-4 Erythro and Threo Diastereomers
   23-5 Epimers
   23-6 Cyclic Structures of Monosaccharides
   23-7 Anomers of Monosaccharides; Mutarotation
   23-8 Reactions of Monosaccharides: Side Reactions in Base
   23-9 Reduction of Monosaccharides
   23-10 Oxidation of Monosaccharides; Reducing Sugars
   23-11 Nonreducing Sugars: Formation of Glycosides
   23-12 Ether and Ester Formation
   23-13 Reactions with Phenylhydrazine: Osazone Formation
   23-14 Chain Shortening: The Ruff Degradation
   23-15 Chain Lengthening: The Kiliani-Fischer Synthesis
   Summary: Reactions of Sugars
   23-16 Fischer’s Proof of the Configuration of Glucose
   23-17 Determination of Ring Size; Periodic Acid Cleavage of Sugars
   23-18 Disaccharides
   23-19 Polysaccharides
   23-20 Nucleic Acids: Introduction
   23-21 Ribonucleosides and Rtbonucleotides
   23-22 The Structure of Ribonucleic Acid
   23-23 Deoxyribose and the Structure of Deoxyribonucleic Acid
   23-24 Additional Functions of Nucleotides
   Chapter 23 Glossary
   Study Problems
  Chapter 24
  Amino Acids, Peptides, and Proteins
   24-1 Introduction
   24-2 Structure and Stereochemistry of the α-Amino Acids
   24-3 Acid-Base Properties of Amino Acids
   24-4 Isoelectric Points and Electrophoresis
   24-5 Synthesis of Amino Acids
   Summary: Syntheses of Amino Acids
   24-6 Resolution of Amino Acids
   24-7 Reactions of Amino Acids
   Summary: Reactions of Amino Acids
   24-8 Structure and Nomenclature of Peptides and Proteins
   24-9 Peptide Structure Determination
   24-10 Solution-Phase Peptide Synthesis
   24-11 Solid-Phase Peptide Synthesis
   24-12 Classification of Proteins
   24-13 Levels of Protein Structure
   24-14 Protein Denaturation
   Chapter 24 Glossary
   Study Problems
  Chapter 25
  Lipids
   25-1 Introduction
   25-2 Waxes
   25-3 Triglycerides
   25-4 Saponification of Fats and Oils; Soaps and Detergents
   25-5 Phospholipids
   25-6 Steroids
   25-7 Prostaglandins
   25-8 Terpenes
   Chapter 25 Glossary
   Study Problems
  Chapter 26
  Synthetic Polymers
   26-1 Introduction
   26-2 Addition Polymers
   26-3 Stereochenustry of Polymers
   26-4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts
   26-5 Natural and Synthetic Rubbers
   26-6 Copolymers of Two or More Monomers
   26-7 Condensation Polymers
   26-8 Polymer Structure and Properties
   Chapter 26 Glossary
   Study Problems
  Appendices
   1A NMR Absorption Positions of Protons in Various Structural Environments
   1B Spin-Spin Coupling Constants
   1C 13C Chemical Shifts in Organic Compounds
   2A Characteristic Infrared Group Frequencies
   2B Characteristic Infrared Absorptions of Functional Groups
   3 The Woodward-Fieser Rules for Predicting Ultraviolet-Visible Spectra
   4A Methods and Suggestions for Proposing Mechanisms
   4B Suggestions for Developing Multistep Syntheses
   5 pKa Values for Representative Compounds
  Mechanism Boxes
   CHAPTER 4 Free-Radical Halogenation
   CHAPTER 6 Allylic Bromination
   The SN2 Reaction
   Inversion of Configuration in the SN2 Reaction
   The Sn1 Reaction
   Racemization in the SN1 Reaction
   Hydride Shift in an Sn1 Reaction
   Methyl Shift in an Sn1 Reaction
   The El Reaction
   Rearrangement in an El Reaction
   The E2 Reaction
  CHAPTER 7 Dehydrohalogenation by the E2 Mechanism
   Stereochemistry of the E2 Reaction
   E2 Dibromination of a Vicinal Dibromide
   Acid-Catalyzed Dehydration of an Alcohol
  CHAPTER 8 Electrophilic Addition to Alkenes
   Ionic Addition of HBr to an Alkene
   Free-Radical Addition of HBr to an Alkene
   Acid-Catalyzed Hydration of an Alkene
   Oxymercuration of an Alkene
   Hydroboration of an Alkene
   Oxidation of a Trialkylborane
   Addition of Halogens to Alkenes
   Formation of Halohydrins
   Epoxidation of Alkenes
   Acid-Catalyzed Opening of Epoxides
  CHAPTER 9 Metal-Ammonia Reduction of an Alkyne
   Acid-Catalyzed Keto-Enol Tautomerism
  CHAPTER 10 Grignard Reactions
   Hydride Reduction of a Carbonyl Group
  CHAPTER 11 Reaction of a Tertiary Alcohol with HBr (SN1)
   Reaction of a Primary Alcohol with HBr (SN2)
   Reaction of Alcohols with PBr3
   (Review): Acid-catalyzed Dehydration of an Alcohol
   The Pinacol Rearrangement
   The Williamson Ether Synthesis
  CHAPTER 14 Cleavage of an Ether by HBr
   Acid-Catalyzed Opening of an Epoxide
   Acid-Catalyzed Opening of an Epoxide in an Alcohol Solution
   Base-Catalyzed Opening of an Epoxide
  CHAPTER 15 1,2- and 1,4-Addition to a Conjugated Diene
   Free-Radical Allylic Bromination
   The Diels-Alder Reaction
  CHAPTER 17 Electrophilic Aromatic Substitution
   Bromination of Benzene
   Nitration of Benzene
   Sulfonation of Benzene
   Friedel-Crafts Alkylation
   Friedel-Crafts Acylation
   Nucleophilic Aromatic Substitution (Addition-Elimination)
   Nucleophilic Aromatic Substitution
   The Birch Reduction
  CHAPTER 18 Nucleophilic Additions to Carbonvl Grouos The Wittig Reaction
   Hydration of Ketones and Aldehydes
   Formation of Cyanohydrins
   Formation of Imines
   Formation of Acetals
   Wolff-Kishner Reduction
  CHAPTER 19
   Electrophilic Aromatic Substitution of Pyridine
   Nucleophilic Aromatic Substitution of Pyridine
   Acylation of an Amine by an Acid Chloride
   Hofmann Elimination
   Cope Elimination of an Amine Oxide
   Diazotization of an Amine
  CHAPTER 20 Hofmann Rearrangement
   Nucleophilic Acyl Substitution of an Ester
   Fischer Esterification
   Esterification Using Diazomethane
  CHAPTER 21 Addition-Elimination Mechanism of Nucleophilic Acyl Substitution
   Conversion of an Acid Chloride to an Anhydride
   Conversion of an Acid Chloride to an Ester
   Conversion of an Acid Chloride to an Amide
   Conversion of an Acid Anhydride to an Ester
   Conversion of an Acid Anhydride to an Amide
   Conversion of an Ester to an Amide (Ammonolysis of an Ester)
   Transesterification
   Saponification of an Ester
   Basic Hydrolysis of an Amide
   Acidic Hydrolysis of an Amide
   Base-Catalyzed Hydrolysis of a Nitrile
   Hydride Reduction of an Ester
   Reaction of an Ester with 2 Moles of a Grignard Reagent
  CHAPTER 22 Alpha Substitution
   Addition of an Enolate to Ketones and Aldehydes (a Condensation)
   Substitution of an Enolate on an Ester (a Condensation)
   Base-Catalyzed Keto-Enol Tautomerism
   Acid-Catalyzed Keto-Enol Tautomerism
   Base-Promoted Halogenation
   Final Steps of the Haloform Reaction
   Acid-Catalyzed Halogenation
   Base-Catalyzed Aldol Condensation
   Acid-Catalyzed Aldol Condensation
   Dehydration of an Aldol
   Claisen Condensation
   1,2-Addition and 1,4-Addition
  CHAPTER 23 Formation of a Cyclic Hemiacetal
   Base-Catalyzed Epimerization of Glucose
   Base-Catalyzed Enediol Rearrangement
  CHAPTER 26 Free-Radical Polymerization
  Cationic Polymerization
  Anionic Polymerization
  Answers to Selected Problems A1
  Photo Credits PC1
  Index i1