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• Title Page
• Copyright
• About the Authors
• Brief Contents
• Contents
• About the Authors
• Preface
• The Keys to Organic Chemistry
• Principles, Preparation, and Problem Solving
• The Keys to Organic Chemistry
• Principles, Preparation, and Problem Solving
• Resources Available Online
• Acknowledgments
• Global Edition Acknowledgments
• Chapter 1. Structure And Bonding
• 1-1 The Origins of Organic Chemistry
• 1-2 Principles of Atomic Structure
• 1-3 Bond Formation: The Octet Rule
• 1-4 Lewis Structures
• 1-5 Multiple Bonding
• Summary: Common Bonding Patterns (Uncharged)
• 1-6 Electronegativity and Bond Polarity
• 1-7 Formal Charges
• Summary: Common Bonding Patterns in Organic Compounds and Ions
• 1-8 Ionic Structures
• 1-9 Resonance
• Problem-Solving Strategy: Drawing And Evaluating Resonance Forms
• 1-10 Structural Formulas
• 1-11 Molecular Formulas and Empirical Formulas
• 1-12 Wave Properties of Electrons in Orbitals
• 1-13 Molecular Orbitals
• 1-14 Pi Bonding
• 1-15 Hybridization and Molecular Shapes
• 1-16 Drawing Three-Dimensional Molecules
• 1-17 General Rules of Hybridization and Geometry
• Summary: Hybridization and Geometry
• 1-18 Bond Rotation
• 1-19 Isomerism
• Essential Terms
• Study Problems
• Chapter 2. Acids And Bases; Functional Groups
• 2-1 Polarity of Bonds and Molecules
• 2-2 Intermolecular Forces
• 2-3 Polarity Effects on Solubilities
• 2-4 Arrhenius Acids and Bases
• 2-5 Brønsted–Lowry Acids and Bases
• 2-6 Strengths of Acids and Bases
• 2-7 Equilibrium Positions of Acid–Base Reactions
• Problem-Solving Strategy: Predicting Acid–Base Equilibrium Positions
• 2-8 Solvent Effects on Acidity and Basicity
• Summary: Acidity and Basicity Limitations in Common Solvents
• 2-9 Effects of Size and Electronegativity on Acidity
• 2-10 Inductive Effects on Acidity
• 2-11 Hybridization Effects on Acidity
• 2-12 Resonance Effects on Acidity and Basicity
• 2-13 Lewis Acids and Bases
• 2-14 The Curved-Arrow Formalism
• 2-15 Hydrocarbons
• 2-16 Functional Groups with Oxygen
• 2-17 Functional Groups with Nitrogen
• Essential Terms
• 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 Monosubstituted Cyclohexanes
• 3-15 Conformations of Disubstituted Cyclohexanes
• Problem-Solving Strategy: Recognizing Cis and Trans Isomers
• 3-16 Bicyclic Molecules
• Essential Terms
• Study Problems
• Chapter 4. The Study Of Chemical Reactions
• 4-1 Introduction
• 4-2 Chlorination of Methane
• 4-3 The Free-Radical Chain Reaction
• 4-4 Equilibrium Constants and Free Energy
• 4-5 Enthalpy and Entropy
• 4-6 Bond-Dissociation Enthalpies
• 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 Selectivity in Halogenation
• 4-14 Hammond’s Postulate
• Problem-Solving Strategy: Proposing Reaction Mechanisms
• 4-15 Radical Inhibitors
• 4-16 Reactive Intermediates
• Summary: Reactive Intermediates
• Essential Terms
• 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
• Essential Terms
• Study Problems
• Chapter 6. Alkyl Halides; Nucleophilic Substitution
• 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 Bimolecular Nucleophilic Substitution: 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 Unimolecular Nucleophilic Substitution: The SN1 Reaction
• 6-14 Stereochemistry of the SN1 Reaction
• 6-15 Rearrangements in SN1 Reactions
• 6-16 Comparison of SN1 and SN2 Reactions
• Summary: Nucleophilic Substitutions
• Summary: Reactions of Alkyl Halides
• Essential Terms
• Study Problems
• Chapter 7. Structure And Synthesis Of Alkenes; Elimination
• 7-1 Introduction
• 7-2 The Orbital Description of the Alkene Double Bond
• 7-3 Elements of Unsaturation
• 7-4 Nomenclature of Alkenes
• 7-5 Nomenclature of Cis-Trans Isomers
• Summary: Rules for Naming Alkenes
• 7-6 Commercial Importance of Alkenes
• 7-7 Physical Properties of Alkenes
• 7-8 Stability of Alkenes
• 7-9 Formation of Alkenes by Dehydrohalogenation of Alkyl Halides
• 7-10 Unimolecular Elimination: The E1 Reaction
• Summary: Carbocation Reactions
• 7-11 Positional Orientation of Elimination: Zaitsev’s Rule
• 7-12 Bimolecular Elimination: The E2 Reaction
• 7-13 Bulky Bases in E2 Eliminations; Hofmann Orientation
• 7-14 Stereochemistry of the E2 Reaction
• 7-15 E2 Reactions in Cyclohexane Systems
• 7-16 Comparison of E1 and E2 Elimination Mechanisms
• Summary: Elimination Reactions
• 7-17 Competition Between Substitutions and Eliminations
• Summary: Substitution and Elimination Reactions of Alkyl Halides
• Problem-Solving Strategy: Predicting Substitutions And Eliminations
• 7-18 Alkene Synthesis by Dehydration of Alcohols
• 7-19 Alkene Synthesis by High-Temperature Industrial Methods
• Problem-Solving Strategy: Proposing Reaction Mechanisms
• Summary: Methods for Synthesis of Alkenes
• Essential Terms
• Study Problems
• Chapter 8. Reactions Of Alkenes
• 8-1 Reactivity of the Carbon–Carbon Double Bond
• 8-2 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 Addition of Halogens to Alkenes
• 8-9 Formation of Halohydrins
• 8-10 Catalytic Hydrogenation of Alkenes
• 8-11 Addition of Carbenes to Alkenes
• 8-12 Epoxidation of Alkenes
• 8-13 Acid-Catalyzed Opening of Epoxides
• 8-14 Syn Dihydroxylation of Alkenes
• 8-15 Oxidative Cleavage of Alkenes
• 8-16 Polymerization of Alkenes
• 8-17 Olefin Metathesis
• Problem-Solving Strategy: Organic Synthesis
• Summary: Reactions of Alkenes
• Summary: Electrophilic Additions to Alkenes
• Summary: Oxidation and Cyclopropanation Reactions of Alkenes
• Essential Terms
• 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; Formation of Acetylide Ions
• 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
• Summary: Reactions of Terminal Alkynes
• Essential Terms
• 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 Reactions of Organometallic Compounds
• 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 by Nucleophilic Additions to Carbonyl Groups
• 10-12 Thiols (Mercaptans)
• Summary: Synthesis of Alcohols from Carbonyl Compounds
• Essential Terms
• 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
• 11-4 Biological Oxidation of Alcohols
• 11-5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
• 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
• Problem-Solving Strategy: Multistep Synthesis
• Summary: Reactions of Alcohols
• Summary: Reactions of Alcohols: O¬H Cleavage
• Summary: Reactions of Alcohols: C¬O Cleavage
• Essential Terms
• 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
• Essential Terms
• 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
• Essential Terms
• Study Problems
• Chapter 14. Ethers, Epoxides, And Thioethers
• 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 Condensation of Alcohols
• Summary: Syntheses of Ethers (Review)
• 14-8 Cleavage of Ethers by HBr and HI
• 14-9 Autoxidation of Ethers
• Summary: Reactions of Ethers
• 14-10 Thioethers (Sulfides) and Silyl Ethers
• 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
• Summary: 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
• Essential Terms
• 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 Buta-1,3-diene
• 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
• 15-12 The Diels–Alder as an Example of a Pericyclic Reaction
• 15-13 Ultraviolet Absorption Spectroscopy
• 15-14 Colored Organic Compounds
• 15-15 UV-Visible Analysis in Biology and Medicine
• Essential Terms
• 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 Hückel’s Rule
• 16-7 Molecular Orbital Derivation of Hückel’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
• Essential Terms
• Study Problems
• Chapter 17. Reactions Of Aromatic Compounds
• 17-1 Electrophilic Aromatic Substitution
• 17-2 Halogenation of Benzene
• 17-3 Nitration of Benzene
• 17-4 Sulfonation of Benzene
• 17-5 Nitration of Toluene: The Effect of Alkyl Substitution
• 17-6 Activating, Ortho, Para-Directing Substituents
• Summary: Activating, Ortho, Para-Directors
• 17-7 Deactivating, Meta-Directing Substituents
• Summary: Deactivating, Meta-Directors
• 17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
• Summary: Directing Effects of Substituents
• 17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
• 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 Aromatic Substitutions Using Organometallic Reagents
• 17-14 Addition Reactions of Benzene Derivatives
• 17-15 Side-Chain Reactions of Benzene Derivatives
• 17-16 Reactions of Phenols
• Problem-Solving Strategy: Synthesis Using Electrophilic Aromatic Substitution
• Summary: Reactions of Aromatic Compounds
• Summary: Electrophilic Aromatic Substitution of Benzene
• Summary: Substitutions of Aryl Halides
• Essential Terms
• Study 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 from Carboxylic Acids
• 18-9 Synthesis of Ketones and Aldehydes from Nitriles
• 18-10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters
• Summary: Syntheses of Ketones and Aldehydes
• 18-11 Reactions of Ketones and Aldehydes: Introduction to Nucleophilic Addition
• 18-12 Hydration of Ketones and Aldehydes
• 18-13 Formation of Cyanohydrins
• 18-14 Formation of Imines
• 18-15 Condensations with Hydroxylamine and Hydrazines
• Summary: Condensations of Amines with Ketones and Aldehydes
• 18-16 Formation of Acetals
• Problem-Solving Strategy: Proposing Reaction Mechanisms
• 18-17 Use of Acetals as Protecting Groups
• 18-18 The Wittig Reaction
• 18-19 Oxidation of Aldehydes
• 18-20 Reductions of Ketones and Aldehydes
• Summary: Reactions of Ketones and Aldehydes
• Summary: Nucleophilic Addition Reactions of Aldehydes and Ketones
• Essential Terms
• 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 Factors that Affect Amine Basicity
• 19-7 Salts of Amines
• 19-8 Spectroscopy of Amines
• 19-9 Reactions of Amines with Ketones and Aldehydes (Review)
• 19-10 Aromatic Substitution of Arylamines and Pyridine
• 19-11 Alkylation of Amines by Alkyl Halides
• 19-12 Acylation of Amines by Acid Chlorides
• 19-13 Formation of Sulfonamides
• 19-14 Amines as Leaving Groups: The Hofmann Elimination
• 19-15 Oxidation of Amines; The Cope Elimination
• 19-16 Reactions of Amines with Nitrous Acid
• 19-17 Reactions of Arenediazonium Salts
• Summary: Reactions of Amines
• 19-18 Synthesis of Amines by Reductive Amination
• 19-19 Synthesis of Amines by Acylation–Reduction
• 19-20 Syntheses Limited to Primary Amines
• Summary: Synthesis of Amines
• Essential Terms
• Study Problems
• Chapter 20. Carboxylic Acids
• 20-1 Introduction
• 20-2 Nomenclature of Carboxylic Acids
• 20-3 Structure and Physical Properties of Carboxylic Acids 1063
• 20-4 Acidity of Carboxylic Acids 1064
• 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
• 20-11 Esterification Using Diazomethane
• 20-12 Condensation of Acids with Amines: Direct Synthesis of Amides
• 20-13 Reduction of Carboxylic Acids
• 20-14 Alkylation of Carboxylic Acids to Form Ketones
• 20-15 Synthesis and Use of Acid Chlorides
• Summary: Reactions of Carboxylic Acids
• Essential Terms
• 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 Spectroscopy of Carboxylic Acid Derivatives
• 21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
• 21-6 Transesterification
• 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 Reagents
• 21-10 Summary of the Chemistry of Acid 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
• Summary: Reactions of Acid Chlorides
• Essential Terms
• Study Problems
• Chapter 22. Condensations And Alpha Substitutions Of Carbonyl Compounds
• 22-1 Introduction
• 22-2 Enols and Enolate Ions
• 22-3 Alkylation of Enolate Ions
• 22-4 Formation and Alkylation of Enamines
• 22-5 Alpha Halogenation of Ketones
• 22-6 Alpha Bromination of Acids: The HVZ Reaction
• 22-7 The Aldol Condensation of Ketones and Aldehydes
• 22-8 Dehydration of Aldol Products
• 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
• 22-13 The Dieckmann Condensation: A Claisen Cyclization
• 22-14 Crossed Claisen Condensations
• 22-15 Syntheses Using b-Dicarbonyl Compounds
• 22-16 The Malonic Ester Synthesis
• 22-17 The Acetoacetic Ester Synthesis
• 22-18 Conjugate Additions: The Michael Reaction
• 22-19 The Robinson Annulation
• Problem-Solving Strategy: Proposing Reaction Mechanisms
• Summary: Enolate Additions and Condensations
• Summary: Reactions of Stabilized Carbanions
• Essential Terms
• Study Problems
• Chapter 23. Carbohydrates And Nucleic Acids
• 23-1 Introduction
• 23-2 Classification of Carbohydrates
• 23-3 Monosaccharides
• 23-4 Cyclic Structures of Monosaccharides
• 23-5 Anomers of Monosaccharides; Mutarotation
• 23-6 Reactions of Monosaccharides: Reduction
• 23-7 Oxidation of Monosaccharides; Reducing Sugars
• 23-8 Nonreducing Sugars: Formation of Glycosides
• 23-9 Ether and Ester Formation
• 23-10 Chain Shortening: The Ruff Degradation
• 23-11 Chain Lengthening: The Kiliani–Fischer Synthesis
• Summary: Reactions of Sugars
• 23-12 Disaccharides
• 23-13 Polysaccharides
• 23-14 Nucleic Acids: Introduction
• 23-15 Ribonucleosides and Ribonucleotides
• 23-16 The Structures of RNA and DNA
• 23-17 Additional Functions of Nucleotides
• Essential Terms
• Study Problems
• Chapter 24. Amino Acids, Peptides, And Proteins
• 24-1 Introduction
• 24-2 Structure and Stereochemistry of the a-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 Laboratory Peptide Synthesis
• 24-11 Classification of Proteins
• 24-12 Levels of Protein Structure
• 24-13 Protein Denaturation
• Essential Terms
• 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
• Essential Terms
• Study Problems
• Chapter 26. Synthetic Polymers
• 26-1 Introduction
• 26-2 Chain-Growth Polymers
• 26-3 Stereochemistry 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 Step-Growth Polymers
• 26-8 Polymer Structure and Properties
• 26-9 Recycling of Plastics
• Essential Terms
• Study Problems
• Appendices
• Appendix 1A. NMR: Spin-Spin Coupling Constants
• Appendix 1B. NMR: Proton Chemical Shifts
• Appendix 1C. NMR: 13C Chemical Shifts in Organic Compounds
• Appendix 2A. IR: Characteristic Infrared Group Frequencies
• Appendix 2B. IR: Characteristic Infrared Absorptions of Functional Groups
• Appendix 3A. Methods and Suggestions for Proposing Mechanisms
• Appendix 3B. Suggestions for Developing Multistep Syntheses
• Appendix 4. pKa Values for Representative Compounds
• Appendix 5. Summary of Organic Nomenclature
• Answers to Selected Problems
• Photo Credits
• Index
• A
• B
• C
• D
• E
• F
• G
• H
• I
• J
• K
• L
• M
• N
• O
• P
• Q
• R
• S
• T
• U
• V
• W
• X
• Y
• Z
• Periodic Table of the Elements