Organic Chemistry [Global Edition]

Cover
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
Copyright
Title Page
Dedication
Contents
Chapter 1: ‘I’m thinking’ – Oh, but are you?
Chapter 2: Renegade perception
Chapter 3: The Pushbacker sting
Chapter 4: ‘Covid’: The calculated catastrophe
Chapter 5: There is no ‘virus’
Chapter 6: Sequence of deceit
Chapter 7: War on your mind
Chapter 8: ‘Reframing’ insanity
Chapter 9: We must have it? So what is it?
Chapter 10: Human 2.0
Chapter 11: Who controls the Cult?
Chapter 12: Escaping Wetiko
Postscript
Appendix: Cowan-Kaufman-Morell Statement on Virus Isolation
Bibliography
Index
Copyright
Title Page
Dedication
Contents
Chapter 1: ‘I’m thinking’ – Oh, but are you?
Chapter 2: Renegade perception
Chapter 3: The Pushbacker sting
Chapter 4: ‘Covid’: The calculated catastrophe
Chapter 5: There is no ‘virus’
Chapter 6: Sequence of deceit
Chapter 7: War on your mind
Chapter 8: ‘Reframing’ insanity
Chapter 9: We must have it? So what is it?
Chapter 10: Human 2.0
Chapter 11: Who controls the Cult?
Chapter 12: Escaping Wetiko
Postscript
Appendix: Cowan-Kaufman-Morell Statement on Virus Isolation
Bibliography
Index