Were you looking for the book with access to MasteringChemistry? This product is the book alone, and does NOT come with access to MasteringChemistry. Buy the book and access card package to save money on this resource. Acclaimed for its clarity and precision, Wades Organic Chemistry maintains scientific rigor while engaging students at all levels. Wade presents a logical, systematic approach to understanding the principles of organic reactivity and the mechanisms of organic reactions. This approach helps students develop the problem-solving strategies and the scientific intuition they will apply throughout the course and in their future scientific work. The Eighth Edition provides enhanced and proven features in every chapter, including new Chapter Goals, Essential Problem-Solving Skills and Hints that encourage both majors and non-majors to think critically and avoid taking "short cuts" to solve problems. Mechanism Boxes and Key Mechanism Boxes strengthen student understanding of Organic Chemistry as a whole while contemporary applications reinforce the relevance of this science to the real world. This package contains: * Organic Chemistry, Eighth Edition
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 1.4 Lewis Structures 1.5 Multiple Bonding 1.6 Electronegativity and Bond Polarity 1.7 Formal Charges 1.8 Ionic Structures 1.9 Resonance 1.10 Structural Formulas 1.11 Molecular Formulas and Empirical Formulas 1.12 Arrhenius Acids and Bases 1.13 Bronsted-Lowry Acids and Bases 1.14 Lewis Acids and Bases Chapter 2: Structure and Properties of Organic Molecules 2.1 Wave Properties of Electrons in Orbitals 2.2 Molecular Orbitals 2.3 Pi Bonding 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 Forces 2.11 Polarity Effects on Solubilities 2.12 Hydrocarbons 2.13 Organic Compounds Containing Oxygen 2.14 Organic Compounds Containing Nitrogen Chapter 3: Structure and Stereochemistry of Alkanes 3.1 Classification of Hydrocarbons 3.2 Molecular Formulas of Alkanes 3.3 Nomenclature of 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 3.14 Conformations of Monosubstituted Cyclohexanes 3.15 Conformations of Disubstituted Cyclohexanes 3.16 Bicyclic Molecules 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 The Hammond Postulate 4.15 Radical Inhibitors 4.16 Reactive Intermediates 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 5.11 Diastereomers 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 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 6.7 Reactions of Alkyl Halides: Substitution and Elimination 6.8 Second-Order Nucleophilic Substitution: The SN2 Reaction 6.9 Generality of the SN2 Reaction 6.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile 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 6.14 Stereochemistry of the SN1 Reaction 6.15 Rearrangements in SN1 Reactions 6.16 Comparison of SN1 and SN2 Reactions 6.17 First-Order Elimination: The E1 Reaction 6.18 Positional Orientation of Elimination: Zaitsevs Rule 6.19 Second-Order Elimination: The E2 Reaction 6.20 Stereochemistry of the E2 Reaction 6.21 Comparison of E1 and E2 Elimination Mechanisms Chapter 7: Structure and Synthesis of Alkenes 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 7.6 Commercial Importance of Alkenes 7.7 Stability of Alkenes 7.8 Physical Properties of Alkenes 7.9 Alkene Synthesis by Elimination of Alkyl Halides 7.10 Alkene Synthesis by Dehydration of Alcohols 7.11 Alkene Synthesis by High-Temperature Industrial Methods 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 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 9.9 Addition of Reactions of Alkynes 9.10 Oxidation of Alkynes 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 10.8 Organometallic Reagents for Alcohol Synthesis 10.9 Addition of Organometallic Reagents to Carbonyl Compounds 10.10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides 10.11 Reduction of the Carbonyl Group: Synthesis of 1 * and 2 * Alcohols 10.12 Thiols (Mercaptans) 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 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 11.11 Unique Reactions of Diols 11.12 Esterification of Alcohols 11.13 Esters of Inorganic Acids 11.14 Reactions of Alkoxides 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 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 13.9 Complex Splitting 13.10 Stereochemical Nonequivalence of Protons 13.11 Time Dependence of NMR Spectroscopy 13.12 Carbon-13 NMR Spectroscopy 13.13 Interpreting Carbon NMR Spectra 13.14 Nuclear Magnetic Resonance Imaging 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 14.8 Cleavage of Ethers by HBr and HI 14.9 Autoxidation of Ethers 14.10 Thioethers (Sulfides) and Silyl Ethers 14.11 Synthesis of Epoxides 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 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 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 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 Huckels Rule 16.7 Molecular Orbital Derivation of Huckels 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 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 17.7 Deactivating, Meta-Directing Substituents 17.8 Halogen Substituents: Deactivating, but Ortho, Para-Directing 17.9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution 17.10 The Friedel-Crafts Alkylation 17.11 The Friedel-Crafts Acylation 17.12 Nucleophilic Aromatic Substitution 17.13 Aromatic Substitutions Using Organometallic Reagents (new section) 17.14 Addition Reactions of Benzene Derivatives 17.15 Side-Chain Reactions of Benzene Derivatives 17.16 Reactions of Phenols 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 18.11 Reactions of Ketones and Aldehydes: Nucleophilic Addition 18.12 The Wittig Reaction 18.13 Hydration of Ketones and Aldehydes 18.14 Formation of Cyanohydrins 18.15 Formation of Imines 18.16 Condensations with Hydroxylamine and Hydrazines 18.17 Formation of Acetals 18.18 Use of Acetals as Protecting Groups 18.19 Oxidation of Aldehydes 18.20 Reductions of Ketones and Aldehydes 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 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 19.18 Synthesis of Amines by Reductive Amination 19.19 Synthesis of Amines by Acylation-Reduction 19.20 Syntheses Limited to Primary Amines Chapter 20: Carboxylic Acids 20.1 Introduction 20.2 Nomenclature of Carboxylic Acids 20.3 Structure and Physical Properties of Carboxylic Acids 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 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 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 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 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 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 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 ss-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 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 23.16 Determination of Ring Size; Periodic Acid Cleavage of Sugars 23.17 Disaccharides 23.18 Polysaccharides 23.19 Nucleic Acids: Introduction 23.20 Ribonucleosides and Ribonucleotides 23.21 The Structure of RNA and DNA 23.22 Additional Functions of Nucleotides Chapter 24: Amino Acids, Peptides, and Proteins 24.1 Introduction 24.2 Structure and Stereochemistry of the Amino Acids 24.3 Acid-Base Properties of Amino Acids 24.4 Isoelectric Points and Electrophoresis 24.5 Synthesis of Amino Acids 24.6 Resolution of Amino Acids 24.7 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 25: Lipids 25.1 Introduction 25.2 Waxes 25.3 Trigylcerides 25.4 Saponification of Fats and Oils; Soaps and Detergents 25.5 Phospholipids 25.6 Steroids 25.7 Prostaglandins 25.8 Terpenes