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• Cover
• Preface
• About This Book
• To the Student of Organic Chemistry
• To the Instructor
• About the Companion Website
• 1 Bonding and Structure of Organic Compounds
• 1.1 Introduction
• 1.2 Electronic Structure of Atoms
• 1.3 Chemical Bonds
• 1.4 Chemical Formulas
• 1.5 The Covalent Bond
• 1.6 Bonding – Concept Summary and Applications
• 1.7 Intermolecular Attractions
• 1.8 Intermolecular Interactions – Concept Summary and Applications
• End of Chapter Problems
• 2 Carbon Functional Groups and Organic Nomenclature
• 2.1 Introduction
• 2.2 Functional Groups
• 2.3 Saturated Hydrocarbons
• 2.4 Organic Nomenclature
• 2.5 Structure and Nomenclature of Alkanes
• 2.6 Unsaturated Hydrocarbons
• 2.7 Structure and Nomenclature of Alkenes
• 2.8 Structure and Nomenclature of Substituted Benzenes
• 2.9 Structure and Nomenclature of Alkynes
• End of Chapter Problems
• 3 Heteroatomic Functional Groups and Organic Nomenclature
• 3.1 Properties and Structure of Alcohols, Phenols, and Thiols
• 3.2 Nomenclature of Alcohols
• 3.3 Nomenclature of Thiols
• 3.4 Structure and Properties of Aldehydes and Ketones
• 3.5 Nomenclature of Aldehydes
• 3.6 Nomenclature of Ketones
• 3.7 Structure and Properties of Carboxylic Acids
• 3.8 Nomenclature of Carboxylic Acids
• 3.9 Structure and Properties of Esters
• 3.10 Structure and Properties of Acid Chlorides
• 3.11 Structure and Properties of Anhydrides
• 3.12 Structure and Properties of Amines
• 3.13 Structure and Properties of Amides
• 3.14 Structure and Properties of Nitriles
• 3.15 Structure and Properties of Ethers
• 3.16 An Overview of Spectroscopy and the Relationship to Functional Groups
• End of Chapter Problems
• 4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities
• 4.1 Introduction
• 4.2 Structural Isomers
• 4.3 Conformational Isomers of Alkanes
• 4.4 Conformational Isomers of Cycloalkanes
• 4.5 Geometric Isomers
• 4.6 Stability of Alkanes
• 4.7 Stability of Alkenes
• 4.8 Stability of Alkynes
• End of Chapter Problems
• 5 Stereochemistry
• 5.1 Introduction
• 5.2 Chiral Stereoisomers
• 5.3 Significance of Chirality
• 5.4 Nomenclature of the Absolute Configuration of Chiral Molecules
• 5.5 Properties of Stereogenic Compounds
• 5.6 Compounds with More Than One Stereogenic Carbon
• 5.7 Resolution of Enantiomers
• End of Chapter Problems
• 6 An Overview of the Reactions of Organic Chemistry
• 6.1 Introduction
• 6.2 Acid–Base Reactions
• 6.3 Addition Reactions
• 6.4 Reduction Reactions
• 6.5 Oxidation Reactions
• 6.6 Elimination Reactions
• 6.7 Substitution Reactions
• 6.8 Pericyclic Reactions
• 6.9 Catalytic Coupling Reactions
• End of Chapter Problems
• 7 Acid–Base Reactions in Organic Chemistry
• 7.1 Introduction
• 7.2 Lewis Acids and Bases
• 7.3 Relative Strengths of Acids and Conjugate Bases
• 7.4 Predicting the Relative Strengths of Acids and Bases
• 7.5 Factors That Affect Acid and Base Strengths
• 7.6 Applications of Acid–Bases Reactions in Organic Chemistry
• End of Chapter Problems
• 8 Addition Reactions Involving Alkenes and Alkynes
• 8.1 Introduction
• 8.2 The Mechanism for Addition Reactions Involving Alkenes
• 8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes)
• 8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes)
• 8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation)
• 8.6 Addition of Water to Alkenes (Hydration of Alkenes)
• 8.7 Addition of Carbenes to Alkenes
• 8.8 The Mechanism for Addition Reactions Involving Alkynes
• 8.9 Applications of Addition Reactions to Synthesis
• End of Chapter Problems
• 9 Addition Reactions Involving Carbonyls and Nitriles
• 9.1 Introduction
• 9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds
• 9.3 Addition of HCN to Carbonyl Compounds
• 9.4 Addition of Water to Carbonyl Compounds
• 9.5 Addition of Alcohols to Carbonyl Compounds
• 9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction)
• 9.7 Addition of Enolates to Carbonyl Compounds
• 9.8 Addition of Amines to Carbonyl Compounds
• 9.9 Mechanism for Addition Reactions Involving Imines
• 9.10 Mechanism for Addition Reactions Involving Nitriles
• 9.11 Applications of Addition Reactions to Synthesis
• End of Chapter Problems
• 10 Reduction Reactions in Organic Chemistry
• 10.1 Introduction
• 10.2 Reducing Agents of Organic Chemistry
• 10.3 Reduction of C=O and C=S Containing Compounds
• 10.4 Reduction of Imines
• 10.5 Reduction of Oxiranes
• 10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes
• End of Chapter Problems
• 11 Oxidation Reactions in Organic Chemistry
• 11.1 Introduction
• 11.2 Oxidation
• 11.3 Oxidation of Alcohols and Aldehydes
• 11.4 Oxidation of Alkenes Without Bond Cleavage
• 11.5 Oxidation of Alkenes with Bond Cleavage
• 11.6 Applications of Oxidation Reactions of Alkenes
• 11.7 Oxidation of Alkynes
• 11.8 Oxidation of Aromatic Compounds
• 11.9 Autooxidation of Ethers and Alkenes
• 11.10 Applications of Oxidation Reactions to Synthesis
• End of Chapter Problems
• 12 Elimination Reactions of Organic Chemistry
• 12.1 Introduction
• 12.2 Mechanisms of Elimination Reactions
• 12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation)
• 12.4 Elimination of Water (Dehydration)
• 12.5 Applications of Elimination Reactions to Synthesis
• End of Chapter Problems
• 13 Spectroscopy Revisited, A More Detailed Examination
• 13.1 Introduction
• 13.2 The Electromagnetic Spectrum
• 13.3 UV‐Vis Spectroscopy and Conjugated Systems
• 13.4 Infrared Spectroscopy
• 13.5 Mass Spectrometry
• 13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy
• End of Chapter Problems
• 14 Free Radical Substitution Reactions Involving Alkanes
• 14.1 Introduction
• 14.2 Types of Alkanes and Alkyl Halides
• 14.3 Chlorination of Alkanes
• 14.4 Bromination of Alkanes
• 14.5 Applications of Free Radical Substitution Reactions
• 14.6 Free Radical Inhibitors
• 14.7 Environmental Impact of Organohalides and Free Radicals
• End of Chapter Problems
• 15 Nucleophilic Substitution Reactions at sp3 Carbons
• 15.1 Introduction
• 15.2 The Electrophile
• 15.3 The Leaving Group
• 15.4 The Nucleophile
• 15.5 Nucleophilic Substitution Reactions
• 15.6 Bimolecular Substitution Reaction Mechanism (SN2 Mechanism)
• 15.7 Unimolecular Substitution Reaction Mechanism (SN1 Mechanism)
• 15.8 Applications of Nucleophilic Substitution Reactions – Synthesis
• End of Chapter Problems
• 16 Nucleophilic Substitution Reactions at Acyl Carbons
• 16.1 Introduction
• 16.2 Mechanism for Acyl Substitution
• 16.3 Substitution Reactions Involving Acid Chlorides
• 16.4 Substitution Reactions Involving Anhydrides
• 16.5 Substitution Reactions Involving Esters
• 16.6 Substitution Reactions Involving Amides
• 16.7 Substitution Reactions Involving Carboxylic Acids
• 16.8 Substitution Reactions Involving Oxalyl Chloride
• 16.9 Substitution Reactions Involving Sulfur Containing Compounds
• 16.10 Applications of Acyl Substitution Reactions
• End of Chapter Problems
• 17 Aromaticity and Aromatic Substitution Reactions
• 17.1 Introduction
• 17.2 Structure and Properties of Benzene
• 17.3 Nomenclature of Substituted Benzene
• 17.4 Stability of Benzene
• 17.5 Characteristics of Aromatic Compounds
• 17.6 Electrophilic Aromatic Substitution Reactions of Benzene
• 17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene
• 17.8 Applications – Synthesis of Substituted Benzene Compounds
• 17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds
• 17.10 Electrophilic Substitution Reactions of Pyrrole
• 17.11 Electrophilic Substitution Reactions of Pyridine
• 17.12 Nucleophilic Aromatic Substitution
• End of Chapter Problems
• 18 Conjugated Systems and Pericyclic Reactions
• 18.1 Conjugated Systems
• 18.2 Pericyclic Reactions
• End of Chapter Problems
• 19 Catalytic Carbon–Carbon Coupling Reactions
• 19.1 Introduction
• 19.2 Reactions of Transition Metal Complexes
• 19.3 Palladium‐Catalyzed Coupling Reactions
• End of Chapter Problems
• 20 Synthetic Polymers and Biopolymers
• 20.1 Introduction
• 20.2 Cationic Polymerization of Alkenes
• 20.3 Anionic Polymerization of Alkenes
• 20.4 Free Radical Polymerization of Alkenes
• 20.5 Copolymerization of Alkenes
• 20.6 Properties of Polymers
• 20.7 Biopolymers
• 20.8 Amino Acids, Monomers of Peptides and Proteins
• 20.9 Acid–Base Properties of Amino Acids
• 20.10 Synthesis of α‐Amino Acids
• 20.11 Reactions of α‐Amino Acids
• 20.12 Primary Structure and Properties of Peptides
• 20.13 Secondary Structure of Proteins
• 20.14 Monosaccharides, Monomers of Carbohydrates
• 20.15 Reactions of Monosaccharides
• 20.16 Disaccharides and Polysaccharides
• 20.17 N‐Glycosides and Amino Sugars
• 20.18 Lipids
• 20.19 Properties and Reactions of Waxes
• 20.20 Properties and Reactions of Triglycerides
• 20.21 Properties and Reactions of Phospholipids
• 20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes
• End of Chapter Problems
• Index
• End User License Agreement