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" Organic chemistry with Mastering Chemistry "
L.G. Wade, Jr.
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BL
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730987
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b550771
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L.G. Wade, Jr.
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Organic chemistry with Mastering Chemistry\ L.G. Wade, Jr.
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| Edition Statement
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8th ed
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| Publication Statement
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Upper Saddle River, N.J.: Prentice Hall ; London : Pearson Education [distributor], 2012
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1 volume ; 28 cm
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0321768140
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: 9780321768148
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Previous edition: 2009.;Includes index.
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| Contents
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Chapter 1: Introduction and Review 1.1 The Origins of Organic Chemistry 1.2 Principles of Atomic Structure1.3 Bond Formation: The Octet Rule1.4 Lewis Structures1.5 Multiple Bonding1.6 Electronegativity and Bond Polarity1.7 Formal Charges1.8 Ionic Structures1.9 Resonance1.10 Structural Formulas1.11 Molecular Formulas and Empirical Formulas1.12 Arrhenius Acids and Bases 1.13 Bronsted-Lowry Acids and Bases1.14 Lewis Acids and BasesChapter 2: Structure and Properties of Organic Molecules2.1 Wave Properties of Electrons in Orbitals2.2 Molecular Orbitals2.3 Pi Bonding2.4 Hybridization and Molecular Shapes2.5 Drawing Three-Dimensional Molecules2.6 General Rules of Hybridization and Geometry 2.7 Bond Rotation 2.8 Isomerism2.9 Polarity of Bonds and Molecules2.10 Intermolecular Forces2.11 Polarity Effects on Solubilities2.12 Hydrocarbons2.13 Organic Compounds Containing Oxygen2.14 Organic Compounds Containing NitrogenChapter 3: Structure and Stereochemistry of Alkanes 3.1 Classification of Hydrocarbons3.2 Molecular Formulas of Alkanes3.3 Nomenclature of Alkanes3.4 Physical Properties of Alkanes3.5 Uses and Sources of Alkanes3.6 Reactions of Alkanes3.7 Structure and Conformations of Alkanes3.8 Conformations of Butane3.9 Conformations of Higher Alkanes3.10 Cycloalkanes3.11 Cis-trans Isomerism in Cycloalkanes3.12 Stabilities of Cycloalkanes; Ring Strain3.13 Cyclohexane Conformations3.14 Conformations of Monosubstituted Cyclohexanes3.15 Conformations of Disubstituted Cyclohexanes3.16 Bicyclic MoleculesChapter 4: The Study of Chemical Reactions4.1 Introduction4.2 Chlorination of Methane4.3 The Free-Radical Chain Reaction4.4 Equilibrium Constants and Free Energy4.5 Enthalpy and Entropy4.6 Bond-Dissociation Enthalpies4.7 Enthalpy Changes in Chlorination4.8 Kinetics and the Rate Equation4.9 Activation Energy and the Temperature Dependence of Rates4.10 Transition States4.11 Rates of Multistep Reactions4.12 Temperature Dependence of Halogenation4.13 Selectivity in Halogenation4.14 The Hammond Postulate4.15 Radical Inhibitors4.16 Reactive IntermediatesChapter 5: Stereochemistry5.1 Introduction5.2 Chirality5.3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms5.4 Optical Activity5.5 Biological Discrimination of Enantiomers5.6 Racemic Mixtures5.7 Enantiomeric Excess and Optical Purity5.8 Chirality of Conformationally Mobile Systems5.9 Chiral Compounds without Asymmetric Atoms5.10 Fischer Projections5.11 Diastereomers5.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons5.13 Meso Compounds5.14 Absolute and Relative Configuration5.15 Physical Properties of Diastereomers5.16 Resolution of EnantiomersChapter 6: Alkyl Halides: Nucleophilic Substitution and Elimination6.1 Introduction6.2 Nomenclature of Alkyl Halides6.3 Common Uses of Alkyl Halides6.4 Structure of Alkyl Halides6.5 Physical Properties of Alkyl Halides6.6 Preparation of Alkyl Halides6.7 Reactions of Alkyl Halides: Substitution and Elimination6.8 Second-Order Nucleophilic Substitution: The SN2 Reaction6.9 Generality of the SN2 Reaction6.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile6.11 Reactivity of the Substrate in SN2 Reactions6.12 Stereochemistry of the SN2 Reaction6.13 First-Order Nucleophilic Substitution: the SN1 Reaction6.14 Stereochemistry of the SN1 Reaction6.15 Rearrangements in SN1 Reactions6.16 Comparison of SN1 and SN2 Reactions6.17 First-Order Elimination: The E1 Reaction6.18 Positional Orientation of Elimination: Zaitsev's Rule6.19 Second-Order Elimination: The E2 Reaction6.20 Stereochemistry of the E2 Reaction6.21 Comparison of E1 and E2 Elimination MechanismsChapter 7: Structure and Synthesis of Alkenes7.1 Introduction7.2 The Orbital Description of the Alkene Double Bond7.3 Elements of Unsaturation7.4 Nomenclature of Alkenes7.5 Nomenclature of Cis-Trans Isomers7.6 Commercial Importance of Alkenes7.7 Stability of Alkenes7.8 Physical Properties of Alkenes7.9 Alkene Synthesis by Elimination of Alkyl Halides7.10 Alkene Synthesis by Dehydration of Alcohols7.11 Alkene Synthesis by High-Temperature Industrial MethodsChapter 8: Reactions of Alkenes8.1 Reactivity of the Carbon-Carbon Double Bond8.2 Electrophilic Addition to Alkenes8.3 Addition of Hydrogen Halides to Alkenes8.4 Addition of Water: Hydration of Alkenes8.5 Hydration by Oxymercuration-Demercuration8.6 Alkoxymercuration-Demercuration8.7 Hydroboration of Alkenes8.8 Addition of Halogens to Alkenes8.9 Formation of Halohydrins8.10 Catalytic Hydrogenation of Alkenes8.11 Addition of Carbenes to Alkenes8.12 Epoxidation of Alkenes8.13 Acid-Catalyzed Opening of Epoxides8.14 Syn Dihydroxylation of Alkenes8.15 Oxidative Cleavage of Alkenes8.16 Polymerization of Alkenes8.17 Olefin MetathesisChapter 9: Alkynes9.1 Introduction9.2 Nomenclature of Alkynes9.3 Physical Properties of Alkynes9.4 Commercial Importance of Alkynes9.5 Electronic Structure of Alkynes9.6 Acidity of Alkynes; Formation of Acetylide Ions9.7 Synthesis of Alkynes from Acetylides9.8 Synthesis of Alkynes by Elimination Reactions9.9 Addition of Reactions of Alkynes9.10 Oxidation of AlkynesChapter 10: Structure and Synthesis of Alcohols10.1 Introduction10.2 Structure and Classification of Alcohols10.3 Nomenclature of Alcohols and Phenols10.4 Physical Properties of Alcohols10.5 Commercially Important Alcohols10.6 Acidity of Alcohols and Phenols10.7 Synthesis of Alcohols: Introduction and Review10.8 Organometallic Reagents for Alcohol Synthesis10.9 Addition of Organometallic Reagents to Carbonyl Compounds10.10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides10.11 Reduction of the Carbonyl Group: Synthesis of 1 and 2 Alcohols10.12 Thiols (Mercaptans)Chapter 11: Reactions of Alcohols11.1 Oxidation States of Alcohols and Related Functional Groups11.2 Oxidation of Alcohols11.3 Additional Methods for Oxidizing Alcohols11.4 Biological Oxidation of Alcohols11.5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates11.6 Reduction of Alcohols11.7 Reactions of Alcohols with Hydrohalic Acids11.8 Reactions of Alcohols with Phosphorus Halides11.9 Reactions of Alcohols with Thionyl Chloride11.10 Dehydration Reactions of Alcohols11.11 Unique Reactions of Diols11.12 Esterification of Alcohols11.13 Esters of Inorganic Acids11.14 Reactions of AlkoxidesChapter 12: Infrared Spectroscopy and Mass Spectrometry12.1 Introduction12.2 The Electromagnetic Spectrum12.3 The Infrared Region12.4 Molecular Vibrations12.5 IR-Active and IR-Inactive Vibrations12.6 Measurement of the IR Spectrum12.7 Infrared Spectroscopy of Hydrocarbons12.8 Characteristic Absorptions of Alcohols and Amines12.9 Characteristic Absorptions of Carbonyl Compounds12.10 Characteristic Absorptions of C-N Bonds12.11 Simplified Summary of IR Stretching Frequencies12.12 Reading and Interpreting IR Spectra (Solved Problems)12.13 Introduction to Mass Spectrometry12.14 Determination of the Molecular Formula by Mass Spectrometry12.15 Fragmentation Patterns in Mass SpectrometryChapter 13: Nuclear Magnetic Resonance Spectroscopy13.1 Introduction13.2 Theory of Nuclear Magnetic Resonance13.3 Magnetic Shielding by Electrons13.4 The NMR Spectrometer13.5 The Chemical Shift13.6 The Number of Signals13.7 Areas of the Peaks13.8 Spin-Spin Splitting13.9 Complex Splitting13.10 Stereochemical Nonequivalence of Protons13.11 Time Dependence of NMR Spectroscopy13.12 Carbon-13 NMR Spectroscopy13.13 Interpreting Carbon NMR Spectra13.14 Nuclear Magnetic Resonance ImagingChapter 14: Ethers, Epoxides and Thioethers14.1 Introduction14.2 Physical Properties of Ethers14.3 Nomenclature of Ethers14.4 Spectroscopy of Ethers14.5 The Williamson Ether Synthesis14.6 Synthesis of Ethers by Alkoxymercuration-Demercuration14.7 Industrial Synthesis: Bimolecular Condensation of Alcohols14.8 Cleavage of Ethers by HBr and HI14.9 Autoxidation of Ethers14.10 Thioethers (Sulfides) and Silyl Ethers14.11 Synthesis of Epoxides14.12 Acid-Catalyzed Ring Opening of Epoxides14.13 Base-Catalyzed Ring Opening of Epoxides14.14 Orientation
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of Epoxide Ring Opening14.15 Reactions of Epoxides with Grignard and Organolithium Reagents14.16 Epoxy Resins: The Advent of Modern GluesChapter 15: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy15.1 Introduction15.2 Stabilities of Dienes15.3 Molecular Orbital Picture of a Conjugated System15.4 Allylic Cations15.5 1,2 and 1,4 Addition to Conjugated Dienes15.6 Kinetic versus Thermodynamic Control in the Addition of HBr15.7 Allylic Radicals15.8 Molecular Orbitals of the Allylic System15.9 Electronic Configurations of the Allyl Radical, Cation and Anion15.10 SN2 Displacement Reactions of Allylic Halides and Tosylates15.11 The Diels-Alder Reaction15.12 The Diels-Alder as an Example of a Pericyclic Reaction15.13 Ultraviolet Absorption SpectroscopyChapter 16: Aromatic Compounds16.1 Introduction: The Discovery of Benzene16.2 The Structure and Properties of Benzene16.3 The Molecular Orbitals of Benzene16.4 The Molecular Orbital Picture of Cyclobutadiene16.5 Aromatic, Antiaromatic, and Nonaromatic Compounds16.6 Huckel's Rule16.7 Molecular Orbital Derivation of Huckel's Rule16.8 Aromatic Ions16.9 Heterocyclic Aromatic Compounds16.10 Polynuclear Aromatic Hydrocarbons16.11 Aromatic Allotropes of Carbon16.12 Fused Heterocyclic Compounds16.13 Nomenclature of Benzene Derivatives16.14 Physical Properties of Benzene and Its Derivatives16.15 Spectroscopy of Aromatic CompoundsChapter 17: Reactions of Aromatic Compounds17.1 Electrophilic Aromatic Substitution17.2 Halogenation of Benzene17.3 Nitration of Benzene17.4 Sulfonation of Benzene17.5 Nitration of Toluene: The Effect of Alkyl Substitution17.6 Activating, Ortho, Para-Directing Substituents17.7 Deactivating, Meta-Directing Substituents17.8 Halogen Substituents: Deactivating, but Ortho, Para-Directing17.9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution17.10 The Friedel-Crafts Alkylation17.11 The Friedel-Crafts Acylation17.12 Nucleophilic Aromatic Substitution17.13 Aromatic Substitutions Using Organometallic Reagents (new section) 17.14 Addition Reactions of Benzene Derivatives17.15 Side-Chain Reactions of Benzene Derivatives17.16 Reactions of PhenolsChapter 18: Ketones and Aldehydes18.1 Carbonyl Compounds18.2 Structure of the Carbonyl Group18.3 Nomenclature of Ketones and Aldehydes18.4 Physical Properties of Ketones and Aldehydes18.5 Spectroscopy of Ketones and Aldehydes18.6 Industrial Importance of Ketones and Aldehydes18.7 Review of Syntheses of Ketones and Aldehydes18.8 Synthesis of Ketones from Carboxylic Acids 18.9 Synthesis of Ketones and Aldehydes from Nitriles18.10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters18.11 Reactions of Ketones and Aldehydes: Nucleophilic Addition18.12 The Wittig Reaction18.13 Hydration of Ketones and Aldehydes18.14 Formation of Cyanohydrins18.15 Formation of Imines18.16 Condensations with Hydroxylamine and Hydrazines18.17 Formation of Acetals18.18 Use of Acetals as Protecting Groups18.19 Oxidation of Aldehydes18.20 Reductions of Ketones and AldehydesChapter 19: Amines19.1 Introduction19.2 Nomenclature of Amines19.3 Structure of Amines19.4 Physical Properties of Amines19.5 Basicity of Amines19.6 Effects on Amine Basicity19.7 Salts of Amines19.8 Spectroscopy of Amines 19.9 Reactions of Amines with Ketones and Aldehydes (Review)19.10 Aromatic Substitution of Arylamines and Pyridine19.11 Alkylation of Amines by Alkyl Halides19.12 Acylation of Amines by Acid Chlorides19.13 Formation of Sulfonamides19.14 Amines as Leaving Groups: The Hofmann Elimination19.15 Oxidation of Amines; The Cope Elimination19.16 Reactions of Amines with Nitrous Acid19.17 Reactions of Arenediazonium Salts19.18 Synthesis of Amines by Reductive Amination19.19 Synthesis of Amines by Acylation-Reduction19.20 Syntheses Limited to Primary AminesChapter 20: Carboxylic Acids20.1 Introduction20.2 Nomenclature of Carboxylic Acids20.3 Structure and Physical Properties of Carboxylic Acids20.4 Acidity of Carboxylic Acids20.5 Salts of Carboxylic Acids20.6 Commercial Sources of Carboxylic Acids20.7 Spectroscopy of Carboxylic Acids20.8 Synthesis of Carboxylic Acids20.9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution20.10 Condensation of Acids with Alcohols: The Fischer Esterification20.11 Esterification Using Diazomethane20.12 Condensation of Acids with Amines: Direct Synthesis of Amides20.13 Reduction of Carboxylic Acids20.14 Alkylation of Carboxylic Acids to Form Ketones20.15 Synthesis and Use of Acid ChloridesChapter 21: Carboxylic Acid Derivatives21.1 Introduction21.2 Structure and Nomenclature of Acid Derivatives21.3 Physical Properties of Carboxylic Acid Derivatives21.4 Spectroscopy of Carboxylic Acid Derivatives21.5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution21.6 Transesterification21.7 Hydrolysis of Carboxylic Acid Derivatives21.8 Reduction of Acid Derivatives21.9 Reactions of Acid Derivatives with Organometallic Reagents21.10 Summary of the Chemistry of Acid Chlorides21.11 Summary of the Chemistry of Anhydrides21.12 Summary of the Chemistry of Esters21.13 Summary of the Chemistry of Amides21.14 Summary of the Chemistry of Nitriles21.15 Thioesters21.16 Esters and Amides of Carbonic AcidChapter 22: Condensations and Alpha Substitutions of Carbonyl Compounds22.1 Introduction22.2 Enols and Enolate Ions22.3 Alkylation of Enolate Ions22.4 Formation and Alkylation of Enamines22.5 Alpha Halogenation of Ketones22.6 Bromination of Acids: The HVZ Reaction22.7 The Aldol Condensation of Ketones and Aldehydes22.8 Dehydration of Aldol Products22.9 Crossed Aldol Condensations22.10 Aldol Cyclizations22.11 Planning Syntheses Using Aldol Condensations22.12 The Claisen Ester Condensation22.13 The Dieckmann Condensation: A Claisen Cyclization22.14 Crossed Claisen Condensations22.15 Syntheses Using ss-Dicarbonyl Compounds22.16 The Malonic Ester Synthesis22.17 The Acetoacetic Ester Synthesis22.18 Conjugate Additions: The Michael Reaction22.19 The Robinson AnnulationChapter 23: Carbohydrates and Nucleic Acids23.1 Introduction23.2 Classification of Carbohydrates23.3 Monosaccharides23.4 Erythro and Threo Diastereomers23.5 Epimers23.6 Cyclic Structures of Monosaccharides23.7 Anomers of Monosaccharides; Mutarotation23.8 Reactions of Monosaccharides: Side Reactions in Base23.9 Reduction of Monosaccharides23.10 Oxidation of Monosaccharides; Reducing Sugars23.11 Nonreducing Sugars: Formation of Glycosides23.12 Ether and Ester Formation23.13 Reactions with Phenylhydrazine: Osazone Formation23.14 Chain Shortening: The Ruff Degradation23.15 Chain Lengthening: The Kiliani-Fischer Synthesis23.16 Determination of Ring Size; Periodic Acid Cleavage of Sugars 23.17 Disaccharides23.18 Polysaccharides23.19 Nucleic Acids: Introduction23.20 Ribonucleosides and Ribonucleotides23.21 The Structure of RNA and DNA 23.22 Additional Functions of NucleotidesChapter 24: Amino Acids, Peptides, and Proteins24.1 Introduction24.2 Structure and Stereochemistry of the Amino Acids24.3 Acid-Base Properties of Amino Acids24.4 Isoelectric Points and Electrophoresis24.5 Synthesis of Amino Acids24.6 Resolution of Amino Acids24.7 Reactions of Amino Acids24.8 Structure and Nomenclature of Peptides and Proteins24.9 Peptide Structure Determination24.10 Solution-Phase Peptide Synthesis24.11 Solid-Phase Peptide Synthesis24.12 Classification of Proteins24.13 Levels of Protein Structure24.14 Protein DenaturationChapter 25: Lipids25.1 Introduction25.2 Waxes25.3 Trigylcerides25.4 Saponification of Fats and Oils; Soaps and Detergents25.5 Phospholipids25.6 Steroids25.7 Prostaglandins25.8 TerpenesChapter 26: 26.1 Introduction26.2 Addition Polymers26.3 Stereochemistry of Polymers26.4 Stereochemical Control of Polymerization; Ziegler-Natta Catalysts26.5 Natural and Synthetic Rubbers26.6 Copolymers of Two or More Monomers26.7 Condensation Polymers26.8 Polymer Structure and Properties
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Chemistry, Organic.
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QD251.L493 2012
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L G Wade
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