Organic Chemistry / Edition 4

Organic Chemistry / Edition 4

by Francis A. Carey

ISBN-10: 0072445238

ISBN-13: 9780072445237

Pub. Date: 06/28/2000

Publisher: McGraw-Hill Companies, The

A Market Leading, Traditional Approach to Organic Chemistry

Throughout all seven editions, Organic Chemistry has been designed to meet the needs of the "mainstream," two-semester, undergraduate organic chemistry course. This best-selling text gives students a solid understanding of organic chemistry by stressing how fundamental reaction mechanisms


A Market Leading, Traditional Approach to Organic Chemistry

Throughout all seven editions, Organic Chemistry has been designed to meet the needs of the "mainstream," two-semester, undergraduate organic chemistry course. This best-selling text gives students a solid understanding of organic chemistry by stressing how fundamental reaction mechanisms function and reactions occur. With the addition of handwritten solutions, new cutting-edge molecular illustrations, updated spectroscopy coverage, seamless integration of molecular modeling exercises, and state-of-the-art multimedia tools, the 7th edition of Organic Chemistry clearly offers the most up-to-date approach to the study of organic chemistry.

Product Details

McGraw-Hill Companies, The
Publication date:
Edition description:
Older Edition
Product dimensions:
8.30(w) x 10.16(h) x 1.99(d)

Table of Contents

Chapter 1 -- Structure Determines Properties1.1 Atoms, Electrons, and Orbitals1.2 Ionic Bonds1.3 Covalent Bonds, Lewis Structures, and the Ocelet Rule1.4 Double Bonds and Triple Bonds1.5 Polar Covalent Bonds and Electronegativity Electrostatic Potential Maps1.6 Structural Formuala of Organic Molecules1.7 Formal Charge1.8 Resonance1.9 The Shape of Some Simple Molecules Molecular Modeling1.10 Molecular Dipole Moments1.11 Curved Arrows and Chemical Reactions1.12 Acids and Bases: The Arrhenius View1.13 Acids and Bases: The Brønsted-Lowry View1.14 What Happened to pKb?1.15 How Structure Affects Acid Strength1.16 Acid-Base Equilibria1.17 Lewis Acids and Lewis Bases1.18 Summary Problems Descriptive Passage and Interpretive Problems 1: Amide Lewis Structures.Chapter 2 -- Alkanes and Cycloakanes: Introduction to Hydrocarbons2.1 Classes of Hydrocarbons2.2 Electron Waves and Chemical Bonds2.3 Bonding in H2: The Valence Bond Model2.4 Bonding in H2: The Molecular Orbital Model2.5 Introduction to Alkanes: Methane, Ethane, and Propane Methane and the Biosphere2.6 sp3 Hybridization and Bonding in Methane2.7 Bonding in Ethane2.8 Isomeric Alkanes: The Butanes2.9 Higher n -Alkanes2.10 The C5H12 Isomers2.11 IUPAC Nomenclature of Unbranched Alkanes What's in a Name? Organic Nonmenclature2.12 Applying the IUPAC Rules: The Names of the C6H14 Isomers2.13 Alkyl Groups2.14 IUPAC Names of Highly Branched Alkanes2.15 Cycloalkane Nomenclature2.16 Sources of Alkanes and Cycloalkanes2.17 PhysicalProperties of Alkanes and Cycloalkanes2.18 Chemical Properties. Combustion of Alkanes2.19 Oxidation-Reduction in Organic Chemistry Thermochemistry2.20 sp2 Hybridization and Bonding in Ethylene2.21 sp Hybridization and Bonding in Acetylene2.22 Which Theory of Chemical Bonding is Best?2.23 Summary Problems Descriptive Passage and Interpretive Problems 2: Some Biochemical Reactions of AlkanesChapter 3 -- Alkanes andCycloalkanes: Conformations and cis-trans Stereoisomers3.1 Conformational Analysis of Ethane3.2 Conformational Analysis of Butane Molecular Mechanics Applied to Alkanes and Cycloalkanes3.3 Conformations of Higher Alkanes3.4 The Shapes of Cycloalkanes: Planar or Nonplanar3.5 Small Rings: Cyclopropane and Cyclobutane3.6 Cyclopentane3.7 Conformations of Cyclohexane3.8 Axial and Equatorial Bonds in Cyclohexane3.9 Conformational Inversion (Ring Flipping) in Cyclohexane3.10 Conformational Analysis of Monosubstituted Cyclohexanes 3.11 Disubstituted Cycloalkanes. Stereoisomers Enthalpy, Free Energy, and Equilibrium Constant3.12 Conformational Analysis of Disubstituted Cyclohexanes3.13 Medium and Large Rings3.14 Polycyclic Ring Systems3.15 Heterocyclic Compounds3.16 Summary ProblemsDescriptive Passage and Interpretive Problems 3: Cylic Forms of Carbohydrates Chapter 4 -- Alcohols and Alkyl Halides4.1 Functional Groups4.2 IUPAC Nomenclature of Alkyl Halides4.3 IUPAC Nomenclature of Alcohols4.4 Classes of Alcohols and Alkyl Halides4.5 Bonding in Alcohols and Alkyl Halides4.6 Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces4.7 Preparation of Alkyl Halides From Alcohols and Hydrogen Halides4.8 Mechanism of the Reaction of Alcohols with Hydrogen Halides4.9 Potential Energy Diagrams for Multistep Reactions. The SN1 Mechanism4.10 Structure, Bonding, and Stability of Carbocations4.11 Effect of Alcohol Structure on Reaction Rate4.12 Reaction of Primary Alcohols with Hydrogen Halides. The SN2 Mechanism4.13 Other Methods for Converting Alcohols to Alkyl Halides4.14 Halogenation of Alkanes4.15 Chlorination of Methane4.16 Structure and Stability of Free Radicals4.17 Mechanism of Methane Chlorination 4.18 Halogenation of Higher Alkanes From Bond Enthalpies to Heats of Reaction4.19 Summary ProblemsDescriptive Passage and Interpretive Problems 4: More About Potential Energy DiagramsChapter 5 -- Structure and Preparation of Alkenes: Elimination Reactions5.1 Alkene Nomenclature5.2 Structure and Bonding in Alkenes Ethylene5.3 Isomerism in Alkenes5.4 Naming Stereoisomeric Alkenes by the E-Z Notational System5.5 Physical Properties on Alkenes5.6 Relative Stabilities of Alkenes5.7 Cycloalkenes5.8 Preparations of Alkenes: Elimination Reactions5.9 Dehydration of Alcohols5.10 Regioselectivity in Alcohol Dehydration: The Zaitsev Rule5.11 Stereoselectivity in Alcohol Dehydration5.12 The E1 and E2 Mechanisms of Alcohol Dehydration5.13 Rearrangements in Alcohol Dehydration5.14 Dehydrohalogenation of Alkyl Halides5.15 The E2 Mechanism of Dehydrohalogenation of Alkyl Halides5.16 Anti Elimination in E2 Reactions: Stereoelectronic Effects5.17 Isotope Effects and the E2 Mechanism5.18 The E1 Mechanism of Dehydrohalogenation of Alkyl Halides5.19 Summary Problems Descriptive Passage and Interpretive Problems 5: A Mechanistic Preview of Addition ReactionsChapter 6 -- Reactions of Alkenes6.1 Hydrogenation of Alkenes6.2 Heats of Hydrogenation6.3 Stereochemistry of Alkene Hydrogenation6.4 Electrophilic Addition of Hydrogen Halides to Alkenes6.5 Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule6.6 Mechanistic Basis for Markovnikov's Rule Rules, Laws, Theories, and the Scientific Method6.7 Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes6.8 Free-Radical Addition of Hydrogen Bromide to Alkenes6.9 Addition of Sulfuric Acid to Alkenes6.10 Acid-Catalyzed Hydration of Alkenes6.11 Thermodynamics of Addition - Elimination Equilibria6.12 Hydroboration-Oxidation of Alkenes6.13 Stereochemistry of Hydroboration-Oxidation6.14 Mechanism of Hydroboration-Oxidation6.15 Addition of Halogens to Alkenes6.16 Stereochemistry of Halogen Addition6.17 Mechanism of Halogen Addition to Alkenes: Halonium Ions6.18 Conversion of Alkenes to Vicinal Halohydrins6.19 Epoxidation of Alkenes6.20 Ozonolysis of Alkenes6.21 Introduction to Organic Chemical Synthesis6.22 Reactions of Alkenes with Alkenes: Polymerization Ethylene and Propane: The Most Important Industrial Organic Chemicals6.23 Summary Problems Descriptive Passage and Interpretive Problems 6: Some Unusual Electrophilic AdditionsChapter 7 -- Stereochemistry7.1 Molecular Chirality: Enantiomers7.2 The Chirality Center7.3 Symmetry in Achiral Structures7.4 Optical Activity7.5 Absolute and Relative Configuration7.6 The Cahn-Ingold-Prelog R-S Notation System7.7 Fischer Projections7.8 Properties of Enantiomers Chiral Drugs7.9 Reactions That Create a Chirality Center7.10 Chiral Molecules With Two Chirality Centers7.11 Achiral Molecules With Two Chirality Centers7.12 Molecules With Multiple Chirality Centers Chirality of Disubstituted Cyclohexanes7.13 Reactions That Produce Diastereomers7.14 Resolution of Enantiomers7.15 Stereoregular Polymers7.16 Chirality Centers Other Than Carbon7.17 Summary Problems Descriptive Passage and Interpretive Problems 7: ProchiralityChapter 8 -- Nucleophilic Substitution8.1 Functional Group Transformation by Nucleophilic Substitution8.2 Relative Reactivity of Halide Leaving Groups8.3 The SN2 Mechanism of Nucleophilic Substitution8.4 Steric Effects and SN2 Reaction Rates8.5 Nucleophiles and Nucleophilicity 8.6 The SN1 Mechanism of Nucleophilic SubstitutionEnzyme-catalyzed Nucleophilic Substitution of Alkyl Halides8.7 Carbocation Stability and SN1 Reaction Rates 8.8 Stereochemistry of SN1 Reactions 8.9 Carbocation Rearrangements in SN1 Reactions 8.10 Effect of Solvent on the Rate of Nucleophilic Substitution8.11 Substitution and Elimination as Competing Reactions8.12 Nucleophilic Substitution of Alkyl Sulfonates8.13 Looking Back: Reactions of Alcohols with Hydrogen Halides 8.14 SummaryProblems Descriptive Passage and Interpretive Problems 8: Nucleophilic SubstitutionChapter 9 -- Alkynes9.1 Sources of Alkynes9.2 Nomenclature9.3 Physical Properties of Alkynes9.4 Structure and Bonding in Alkynes: sp Hybridization 9.5 Acidity of Acetylene and Terminal Alkynes9.6 Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes9.7 Preparation of Alkynes by Elimination Reactions9.8 Reactions of Alkynes9.9 Hydrogenation of Alkynes9.10 Metal-Ammonia Reduction of Alkynes9.11 Addition of Hydrogen Halides to Alkynes9.12 Hydration of Alkynes9.13 Addition of Halogens to AlkynesSome Things That Can Be Made From Acetylene...But Aren't9.14 Ozonolysis of Alkynes9.15 Summary Problems Descriptive Passage and Interpretive Problems 9: Thinking Mechanistically About AlkynesChapter 10 - Conjugation in alkadienes and Allylic Systems 10.1 The Allyl Group10.2 Allylic Carbocations 10.3 SN1 Reactions of Allylic Halides10.4 SN2 Reactions of Allylic Halides10.5 Allylic Free Radicals10.6 Allylic Halogenation10.7 Allylic Anions10.8 Classes of Dienes10.9 Relative Stabilities of Dienes10.10 Bonding in Conjugated Dienes10.11 Bonding in Allenes 10.12 Preparation of Dienes10.13 Addition of Hydrogen Halides to Conjugated Dienes10.14 Halogen Addition to Dienes10.15 The Diels-Alder ReactionDienes Polymers10.16 The Molecular Orbitals of Ethylene and 1,3-Butadiene10.17 A Molecular Orbital Analysis of the Diels-Alder Reaction10.18 SummaryProblems Descriptive Passage and Interpretive Passages 10: Intramolecular and Retro Diels-Alder ReactionsChapter 11 -Arenes and Aromaticity11.1 Benzene11.2 Kekule and the Structure of Benzene11.3 A Resonance Picture of Bonding in Benzene11.4 The stability of Benzene11.5 An Orbital hybridization View of Bonding in Benzene11.6 The p Molecular Orbitals of Benzene11.7 Substituted Derivatives of Benzene and their Nomenclature11.8 Polycyclic Aromatic Hydrocarbons11.9 Physical Properties of ArenesCarbon Clusters, Fullerenes, and Nanotubes11.10 Reactions of Arenes. A Preview.11.11 The Birch Reduction11.12 Free-Radical Halogenation of Alkylbenzenes11.13 Oxidation of Alkylbenzenes11.14 SN1 Reactions of Benzylic Halides11.15 SN2 Reactions of Benzylic Halides11.16 Preparation of Alkenylbenzenes11.17 Addition Reactions of Alkenylbenzenes11.18 Polymerization of Styrene11.19 Cyclobutadiene and Cyclooctatetraene11.20 Huckel's Rule11.21 Annulenes11.22 Aromatic Ions11.23 Heterocyclic Aromatic Compounds11.24 Heterocyclic Aromatic Compounds and Huckel's Rule11.25 SummaryProblemsDescriptive Passage and Interpretive Problems 11: The Hammett EquationCHAPTER 12 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 12.1 Representative Electrophilic Aromatic Substitution Reactions of Benzene 12.2 Mechanistic Principles of Electrophilic Aromatic Substitution 12.3 Nitration of Benzene 12.4 Sulfonation of Benzene 12.5 Halogenation of Benzene 12.6 Friedel–Crafts Alkylation of Benzene 12.7 Friedel–Crafts Acylation of Benzene 12.8 Synthesis of Alkylbenzenes by Acylation–Reduction 12.9 Rate and Regioselectivity in Electrophilic Aromatic Substitution 12.10 Rate and Regioselectivity in the Nitration of Toluene 12.11 Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene 12.12 Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents 12.13 Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents 12.14 Substituent Effects in Electrophilic Aromatic Substitution: Halogens 12.15 Multiple Substituent Effects 12.16 Regioselective Synthesis of Disubstituted Aromatic Compounds 12.17 Substitution in Naphthalene 12.18 Substitution in Heterocyclic Aromatic Compounds 12.19 SUMMARY Problems Descriptive Passage and Interpretive Problems 12: Nucleophilic Aromatic SubstitutionCHAPTER 13 SPECTROSCOPY 13.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation 13.2 Principles of Molecular Spectroscopy: Quantized Energy States 13.3 Introduction to 1 H NMR Spectroscopy 13.4 Nuclear Shielding and 1 H Chemical Shifts 13.5 Effects of Molecular Structure on 1 H Chemical Shifts Ring Currents—Aromatic and Antiaromatic 13.6 Interpreting 1 H NMR Spectra 13.7 Spin–Spin Splitting in 1 H NMR Spectroscopy 13.8 Splitting Patterns: The Ethyl Group 13.9 Splitting Patterns: The Isopropyl Group 13.10 Splitting Patterns: Pairs of Doublets 13.11 Complex Splitting Patterns 13.12 1 H NMR Spectra of Alcohols Magnetic Resonance Imaging (MRI) 13.13 NMR and Conformations 13.14 13 C NMR Spectroscopy 13.15 13 C Chemical Shifts 13.16 13 C NMR and Peak Intensities 13.17 13 C 1 H Coupling 13.18 Using DEPT to Count Hydrogens Attached to 13C 13.19 2D NMR: COSY and HETCOR13.20 Introduction to Infrared Spectroscopy Spectra by the Thousands 13.21 Infrared Spectra13.22 Characteristic Absorption Frequencies13.23 Ultraviolet-Visible (UV-VIS) Spectroscopy 13.24 Mass Spectrometry 13.25 Molecular Formula as a Clue to Structure Gas Chromatography, GC/MS, and MS/MS 13.26 SUMMARY ProblemsDescriptive Passage and Interpretive Problems 13: Calculating Aromatic 13C Chemical Shifts CHAPTER 14 ORGANOMETALLIC COMPOUNDS 14.1 Organometallic Nomenclature 14.2 Carbon–Metal Bonds in Organometallic Compounds 14.3 Preparation of Organolithium Compounds 14.4 Preparation of Organomagnesium Compounds: Grignard Reagents 14.5 Organolithium and Organomagnesium Compounds as Brønsted Bases 14.6 Synthesis of Alcohols Using Grignard Reagents 14.7 Synthesis of Alcohols Using Organolithium Reagents 14.8 Synthesis of Acetylenic Alcohols 14.9 Retrosynthetic Analysis 14.10 Preparation of Tertiary Alcohols from Esters and Grignard Reagents 14.11 Alkane Synthesis Using Organocopper Reagents 14.12 An Organozinc Reagent for Cyclopropane Synthesis 14.13 Carbenes and Carbenoids 14.14 Transition-Metal Organometallic Compounds An Organometallic Compound That Occurs Naturally: Coenzyme B12 14.15 Homogeneous Catalytic Hydrogenation 14.16 Olefin Metathesis 14.17 Ziegler–Natta Catalysis of Alkene Polymerization 14.18 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 14: Oxymercuration CHAPTER 15 ALCOHOLS, DIOLS, AND THIOLS 15.1 Sources of Alcohols 15.2 Preparation of Alcohols by Reduction of Aldehydes and Ketones 15.3 Preparation of Alcohols by Reduction of Carboxylic Acids and Esters 15.4 Preparation of Alcohols from Epoxides 15.5 Preparation of Diols 15.6 Reactions of Alcohols: A Review and a Preview 15.7 Conversion of Alcohols to Ethers 15.8 Esterification 15.9 Esters of Inorganic Acids 15.10 Oxidation of Alcohols 15.11 Biological Oxidation of Alcohols Economic and Environmental Factors in Organic Synthesis15.12 Oxidative Cleavage of Vicinal Diols 15.13 Thiols 15.14 Spectroscopic Analysis of Alcohols and Thiols 15.15 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 15: The Pinacol RearrangementCHAPTER 16 ETHERS, EPOXIDES, AND SULFIDES 16.1 Nomenclature of Ethers, Epoxides, and Sulfides 16.2 Structure and Bonding in Ethers and Epoxides 16.3 Physical Properties of Ethers 16.4 Crown Ethers 16.5 Preparation of Ethers Polyether Antibiotics 16.6 The Williamson Ether Synthesis 16.7 Reactions of Ethers: A Review and a Preview 16.8 Acid-Catalyzed Cleavage of Ethers 16.9 Preparation of Epoxides: A Review and a Preview 16.10 Conversion of Vicinal Halohydrins to Epoxides 16.11 Reactions of Epoxides: A Review and a Preview 16.12 Nucleophilic Ring Opening of Epoxides 16.13 Acid-Catalyzed Ring Opening of Epoxides 16.14 Epoxides in Biological Processes 16.15 Preparation of Sulfides 16.16 Oxidation of Sulfides: Sulfoxides and Sulfones 16.17 Alkylation of Sulfides: Sulfonium Salts 16.18 Spectroscopic Analysis of Ethers, Epoxides, and Sulfides 16.19 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 16: Epoxide Rearrangements and the NIH Shift CHAPTER 17 ALDEHYDES AND KETONES: NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 17.1 Nomenclature 17.2 Structure and Bonding: The Carbonyl Group 17.3 Physical Properties 17.4 Sources of Aldehydes and Ketones 17.5 Reactions of Aldehydes and Ketones: A Review and a Preview 17.6 Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones 17.7 Cyanohydrin Formation 17.8 Acetal Formation 17.9 Acetals as Protecting Groups 17.10 Reaction with Primary Amines: Imines Imines in Biological Chemistry 17.11 Reaction with Secondary Amines: Enamines 17.12 The Wittig Reaction 17.13 Planning an Alkene Synthesis via the Wittig Reaction 17.14 Stereoselective Addition to Carbonyl Groups 17.15 Oxidation of Aldehydes 17.16 Baeyer–Villiger Oxidation of Ketones 17.17 Spectroscopic Analysis of Aldehydes and Ketones 17.18 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 17: Alcohols, Aldehydes, and Carbohydrates CHAPTER 18 ENOLS AND ENOLATES 18.1 The -Hydrogen and Its pKa 18.2 The Aldol Condensation 18.3 Mixed Aldol Condensations 18.4 Alkylation of Enolate Ions 18.5 Enolization and Enol Content18.6 Stabilized Enols 18.7 Halogenation of Aldehydes and Ketones 18.8 Mechanism of Halogenation of Aldehydes and Ketones 18.9 The Haloform Reaction 18.10 Some Chemical and Stereochemical Consequences of Enolization The Haloform Reaction and the Biosynthesis of Trihalomethanes 18.11 Effects of Conjugation in ,-Unsaturated Aldehydes and Ketones 18.12 Conjugate Addition to ,-Unsaturated Carbonyl Compounds 18.13 Addition of Carbanions to ,-Unsaturated Ketones: The Michael Reaction 18.14 Conjugate Addition of Organocopper Reagents to ,-Unsaturated Carbonyl Compounds 18.15 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 18: Enolate Regiochemistry and StereochemistryCHAPTER 19 CARBOXYLIC ACIDS 19.1 Carboxylic Acid Nomenclature 19.2 Structure and Bonding 19.3 Physical Properties 19.4 Acidity of Carboxylic Acids 19.5 Salts of Carboxylic Acids 19.6 Substituents and Acid Strength 19.7 Ionization of Substituted Benzoic Acids 19.8 Dicarboxylic Acids 19.9 Carbonic Acid 19.10 Sources of Carboxylic Acids 19.11 Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents 19.12 Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles 19.13 Reactions of Carboxylic Acids: A Review and a Preview 19.14 Mechanism of Acid-Catalyzed Esterification 19.15 Intramolecular Ester Formation: Lactones 19.16 Alpha Halogenation of Carboxylic Acids: The Hell–Volhard–Zelinsky Reaction 19.17 Decarboxylation of Malonic Acid and Related Compounds 19.18 Spectroscopic Analysis of Carboxylic Acids 19.19 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 19: Lactonization MethodsCHAPTER 20 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 20.1 Nomenclature of Carboxylic Acid Derivatives 20.2 Structure and Reactivity of Carboxylic Acid Derivatives 20.3 General Mechanism for Nucleophilic Acyl Substitution 20.4 Nucleophilic Acyl Substitution in Acyl Chlorides 20.5 Nucleophilic Acyl Substitution in Acid Anhydrides 20.6 Sources of Esters 20.7 Physical Properties of Esters 20.8 Reactions of Esters: A Review and a Preview 20.9 Acid-Catalyzed Ester Hydrolysis 20.10 Ester Hydrolysis in Base: Saponification 20.11 Reaction of Esters with Ammonia and Amines 20.12 Amides 20.13 Hydrolysis of Amides 20.14 Lactams Lactum Antibiotics 20.15 Preparation of Nitriles20.16 Hydrolysis of Nitriles 20.17 Addition of Grignard Reagents to Nitriles 901 20.18 Spectroscopic Analysis of Carboxylic Acid Derivatives 20.19 SUMMARY PROBLEMSDescriptive Passage and Interpretive Problems 20: Thioesters CHAPTER 21 ESTER ENOLATES 21.1 Ester Hydrogens and Their pKa ’s 21.2 The Claisen Condensation 21.3 Intramolecular Claisen Condensation: The Dieckmann Reaction 21.4 Mixed Claisen Condensations 21.5 Acylation of Ketones with Esters 21.6 Ketone Synthesis via -Keto Esters21.7 The Acetoacetic Ester Synthesis 21.8 The Malonic Ester Synthesis 21.9 Michael Additions of Stabilized Anions 21.10 Reactions of LDA-Generated Ester Enolates 21.11 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 21: The Enolate Chemistry of DianionsCHAPTER 22 AMINES 22.1 Amine Nomenclature 22.2 Structure and Bonding 22.3 Physical Properties 22.4 Basicity of Amines Amines as Natural Products22.5 Tetraalkylammonium Salts as Phase-Transfer Catalysts 22.6 Reactions That Lead to Amines: A Review and a Preview 22.7 Preparation of Amines by Alkylation of Ammonia 22.8 The Gabriel Synthesis of Primary Alkylamines 22.9 Preparation of Amines by Reduction 22.10 Reductive Amination 22.11 Reactions of Amines: A Review and a Preview 22.12 Reaction of Amines with Alkyl Halides 22.13 The Hofmann Elimination 22.14 Electrophilic Aromatic Substitution in Arylamines 22.15 Nitrosation of Alkylamines 22.16 Nitrosation of Arylamines 22.17 Synthetic Transformations of Aryl Diazonium Salts 22.18 Azo Coupling From Dyes to Sulfa Drugs 22.19 Spectroscopic Analysis of Amines 22.20 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 22: Synthetic Applications of EnaminesCHAPTER 23 ARYL HALIDES23.1 Bonding in Aryl Halides 23.2 Sources of Aryl Halides 23.3 Physical Properties of Aryl Halides 23.4 Reactions of Aryl Halides: A Review and a Preview 23.5 Nucleophilic Substitution in Nitro-Substituted Aryl Halides 23.6 The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution 23.7 Related Nucleophilic Aromatic Substitution Reactions 23.8 The Elimination–Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne 23.9 Diels–Alder Reactions of Benzyne 23.10 m-Benzyne and p-Benzyne 23.11 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 23: The Heck ReactionCHAPTER 24 PHENOLS 24.1 Nomenclature 24.2 Structure and Bonding 24.3 Physical Properties 24.4 Acidity of Phenols 24.5 Substituent Effects on the Acidity of Phenols 24.6 Sources of Phenols 24.7 Naturally Occurring Phenols 24.8 Reactions of Phenols: Electrophilic Aromatic Substitution 24.9 Acylation of Phenols 24.10 Carboxylation of Phenols: Aspirin and the Kolbe–Schmitt Reaction 24.11 Preparation of Aryl Ethers Agent Orange and Dioxin 24.12 Cleavage of Aryl Ethers by Hydrogen Halides 24.13 Claisen Rearrangement of Allyl Aryl Ethers 24.14 Oxidation of Phenols: Quinones 24.15 Spectroscopic Analysis of Phenols 24.16 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 24: Directed Metalation of Aryl EthersCHAPTER 25 CARBOHYDRATES25.1 Classification of Carbohydrates 25.2 Fischer Projections and D–L Notation 25.3 The Aldotetroses 25.4 Aldopentoses and Aldohexoses 25.5 A Mnemonic for Carbohydrate Configurations 25.6 Cyclic Forms of Carbohydrates: Furanose Forms25.7 Cyclic forms of Carbohydrates: Pyranose Forms 25.8 Mutarotation and the Anomeric Effect 25.9 Ketoses 25.10 Deoxy Sugars 25.11 Amino Sugars 25.12 Branched-Chain Carbohydrates 25.13 Glycosides 25.14 Disaccharides 25.15 Polysaccharides How Sweet It Is! 25.16 Reactions of Carbohydrates 25.17 Reduction of Monosaccharides 25.18 Oxidation of Monosaccharides 25.19 Cyanohydrin Formation and Chain Extension 25.20 Epimerization, Isomerization, and Retro-Aldol Cleavage 25.21 Acylation and Alkylation of Hydroxyl Groups 25.22 Periodic Acid Oxidation 25.23 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 25: Emil Fisher and the structure of (+) - GlucoseCHAPTER 26 LIPIDS26.1 Acetyl Coenzyme A 26.2 Fats, Oils, and Fatty Acids 26.3 Fatty Acid Biosynthesis 26.4 Phospholipids 26.5 Waxes 26.6 Prostaglandins Nonsteroidal Antiinflammatory Drugs (NSAIDS) and COX-2 Inhibitors 26.7 Terpenes: The Isoprene Rule 26.8 Isopentenyl Diphosphate: The Biological Isoprene Unit 26.9 Carbon–Carbon Bond Formation in Terpene Biosynthesis 26.10 The Pathway from Acetate to Isopentenyl Diphosphate 26.11 Steroids: Cholesterol26.12 Vitamin D Good Cholesterol? Bad Cholesterol? What’s the Difference? 26.13 Bile Acids 26.14 Corticosteroids 26.15 Sex Hormones 26.16 Carotenoids Anabolic Steroids Crocuses Make Saffron from Carotenes 26.17 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 26: Polyketides CHAPTER 27 AMINO ACIDS, PEPTIDES, AND PROTEINS 27.1 Classification of Amino Acids 27.2 Stereochemistry of Amino Acids 27.3 Acid–Base Behavior of Amino Acids 27.4 Synthesis of Amino Acids Electrophoresis 27.5 Reactions of Amino Acids 27.6 Some Biochemical Reactions of Amino Acids27.7 Peptides27.8 Introduction to Peptide Structure Determination27.9 Amino Acid Analysis 27.10 Partial Hydrolysis of Peptides 27.11 End Group Analysis 27.12 Insulin 27.13 The Edman Degradation and Automated Sequencing of Peptides Peptide Mapping and MALDI Mass Spectrometry27.14 The Strategy of Peptide Synthesis 27.15 Amino Group Protection 27.16 Carboxyl Group Protection 27.17 Peptide Bond Formation 27.18 Solid-Phase Peptide Synthesis: The Merrifield Method 27.19 Secondary Structures of Peptides and Proteins 27.20 Tertiary Structure of Polypeptides and Proteins 27.21 Coenzymes Oh NO! It’s Inorganic! 27.22 Protein Quaternary Structure: Hemoglobin 27.23 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 27: Amino Acids in Enantioselective Synthesis CHAPTER 28 NUCLEOSIDES, NUCLEOTIDES, AND NUCLEIC ACIDS 28.1 Pyrimidines and Purines28.2 Nucleosides 28.3 Nucleotides 28.4 Bioenergetics 28.5 ATP and Bioenergetics 28.6 Phosphodiesters, Oligonucleotides, and Polynucleotides 28.7 Nucleic Acids 28.8 Secondary Structure of DNA: The Double Helix “It Has Not Escaped Our Notice . . .” 28.9 Tertiary Structure of DNA: Supercoils 28.10 Replication of DNA 28.11 Ribonucleic Acids 28.12 Protein Biosynthesis RNA World 28.13 AIDS 28.14 DNA Sequencing28.15 The Human Genome Project28.16 DNA Profiling and the Polymerase Chain Reaction 28.17 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 28: Oligonucleotide SynthesisCHAPTER 29 SYNTHETIC POLYMERS 29.1 Some Background 29.2 Polymer Nomenclature 29.3 Classification of Polymers: Reaction Type 29.4 Classification of Polymers: Chain-Growth and Step-Growth 29.5 Classification of Polymers: Structure 29.6 Classification of Polymers: Properties 29.7 Addition Polymers: A Review and a Preview 29.8 Chain Branching in Free-Radical Polymerization 29.9 Anionic Polymerization: Living Polymers 29.10 Cationic Polymerization 29.11 Polyamides 29.12 Polyesters 29.13 Polycarbonates 29.14 Polyurethanes 29.15 Copolymers 29.16 SUMMARY PROBLEMS Descriptive Passage and Interpretive Problems 29: Chemical Modification of PolymersGLOSSARY CREDITS INDEX

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