CiNii 図書 - Organic chemistry

In this innovative text, Bruice balances coverage of traditional topics with bioorganic chemistry to show how organic chemistry is related to biological systems and to our daily lives. Functional groups are organized around mechanistic similarities, emphasizing what functional groups do rather than how they are made. Tying together the reactivity of a functional group and the synthesis of compounds resulting from its reactivity prevents students from needing to memorize lists of unrelated reactions. The Sixth Edition has been revised and streamlined throughout to enhance clarity and accessibility, and adds a wealth of new problems and problem-solving strategies.

I AN INTRODUCTION TO THE STUDY OF CHEMISTRY 1 Electronic Structure and Bonding * Acids and Bases 1.1 The Structure of an Atom 1.2 How Electrons in an Atom are Distributed 1.3 Ionic and Covalent Bonds 1.4 How the Structure of a Compound is Represented 1.5 Atomic Orbitals 1.6 An Introduction to Molecular Orbital Theory 1.7 How Single Bonds Are Formed in Organic Compounds 1.8 How a Double Bond is Formed: The Bonds in Ethene 1.9 How a Triple Bond is Formed: The Bonds in Ethyne 1.10 Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion 1.11 The Bonds in Water 1.12 The Bonds in Ammonia and in the Ammonium Ion 1.13 The Bond in a Hydrogen Halide 1.14 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 1.15 The Dipole Moments of Molecules 1.16 An Introduction to Acids and Bases 1.17 pka and pH 1.18 Organic Acids and Bases 1.19 How to Predict the Outcome of an Acid-Base Reaction 1.20 How to Determine the Position of Equilibrium 1.21 How the Structure of an Acid Affects its pka Value 1.22 How Substituents Affect the Strength of an Acid 1.23 An Introduction to Delocalized Electrons 1.24 A Summary of the Factors that Determine Acid Strength 1.25 How pH Affects the Structure of an Organic Compound 1.26 Buffer Solutions 1.27 Lewis Acids and Bases 2 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure 2.1 How Alkyl Substituents Are Named 2.2 The Nomenclature of Alkanes 2.3 The Nomenclature of Cycloalkanes * Skeletal Structures 2.4 The Nomenclature of Alkyl Halides 2.5 The Nomenclature of Ethers 2.6 The Nomenclature of Alcohols 2.7 The Nomenclature of Amines 2.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 2.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines 2.10 Rotation Occurs About Carbon-Carbon Single Bonds 2.11 Some Cycloalkanes Have Angle Strain 2.12 Conformers of Cyclohexane 2.13 Conformers of Monosubstituted Cyclohexanes 2.14 Conformers of Disubstituted Cyclohexanes 2.15 Fused Cyclohexane Rings II ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION 3 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity * Thermodynamics and Kinetics 3.1 Molecular Formulas and the Degree of Unsaturation 3.2 The Nomenclature of Alkenes 3.3 The Structures of Alkenes 3.4 Alkenes Can Have Cis and Trans Isomers 3.5 Naming Alkenes Using the E,Z System 3.6 How Alkenes React * Curved Arrows Show the Flow of Electrons 3.7 Thermodynamics and Kinetics 3.8 The Rate of a Reaction and the Rate Constant for a Reaction 3.9 A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction 4 The Reactions of Alkenes 4.1 The Addition of a Hydrogen Halide to an Alkene 4.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon 4.3 What Does the Structure of the Transition State Look Like? 4.4 Electrophilic Addition Reactions Are Regioselective 4.5 The Addition of Water to an Alkene 4.6 The Addition of an Alcohol to an Alkene 4.7 A Carbocation Will Rearrange If It Can Form a More Stable Carbocation 4.8 The Addition of a Halogen to an Alkene 4.9 Oxymercuration-Reduction and Alkoxymercuration-Reduction Are Other Ways to Add Water or an Alcohol to an Alkene 4.10 The Addition of a Peroxyacid to an Alkene 4.11 The Addition of Borane to an Alkene: Hydroboration-Oxidation 4.12 The Addition of Hydrogen to an Alkene 4.13 The Relative Stabilities of Alkenes 4.14 Reactions and Synthesis 5 Stereochemistry: The Arrangement of Atoms in Space
The Stereochemistry of Addition Reactions 5.1 Cis-Trans Isomers Result from Restricted Rotation 5.2 A Chiral Object Has a Nonsuperimposable Mirror Image 5.3 An Asymmetric Center Is a Cause of Chirality in a Molecule 5.4 Isomers with One Asymmetric Center 5.5 Asymmetric Centers and Stereocenters 5.6 How to Draw Enantiomers 5.7 Naming Enantiomers by the R,S System 5.8 Chiral Compounds Are Optically Active 5.9 How Specific Rotation is Measured 5.10 Enantiomeric Excess 5.11 Isomers with More than One Asymmetric Center 5.12 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 5.13 How to Name Isomers with More than One Asymmetric Center 5.14 Reactions of Compounds that Contain an Asymmetric Center 5.15 Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations 5.16 How Enantiomers Can Be Separated 5.17 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers 5.18 Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions 5.19 The Stereochemistry of Electrophilic addition Reactions of Alkenes 5.20 The Stereochemistry of Enzyme-Catalyzed Reactions 5.21 Enantiomers Can Be Distinguished by Biological Molecules 6 The Reactions of Alkynes: An Introduction to Multistep Synthesis 6.1 The Nomenclature of Alkynes 6.2 How to Name a Compound That Has More than One Functional Group 6.3 The Physical Properties of Unsaturated Hydrocarbons 6.4 The Structure of Alkynes 6.5 How Alkynes React 6.6 The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne 6.7 The Addition of Water to an Alkyne 6.8 The Addition of Borane to an Alkyne: Hydroboration-Oxidation 6.9 The Addition if Hydrogen to an Alkyne 6.10 A Hydrogen Bonded to an sp Carbon is "Acidic" 6.11 Synthesis Using Acetylide Ions 6.12 Designing a Synthesis I: An Introduction to Multistep Synthesis 7 Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa * More About Molecular Orbital Theory 7.1 Delocalized Electrons Explain Benzene's Structure 7.2 The Bonding in Benzene 7.3 Resonance Contributors and the Resonance Hybrid 7.4 How to Draw Resonance Contributors 7.5 The Predicted Stabilities of Resonance Contributors 7.6 Delocalized Energy Is the Additional Stability Delocalized Electrons Give to a Compound 7.7 Examples That Show How Delocalized Electrons Affect Stability 7.8 A Molecular Orbital Description of Stability 7.9 How Delocalized Electrons Affect pKa Values 7.10 Delocalized Electrons Can Affect the Product of a Reaction 7.11 Thermodynamic Versus Kinetic Control of Reactions 7.12 The Diels-Adler Reaction Is a 1,4-Addition Reaction III SUBSTITUTION AND ELIMINATION REACTIONS 8 Substitution Reactions of Alkyl Halides 8.1 The Mechanism For an SN2 Reaction 8.2 Factors That Affect SN2 Reactions 8.3 The Reversibility of an SN2 Reaction Depends on the Basicities of the Leaving Groups in the Forward and Reverse Directions 8.4 The Mechanism for an SN1 Reaction 8.5 Factors That Affect SN1 Reactions 8.6 More About the Stereochemistry of SN2 and SN1Reactions 8.7 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides 8.8 Competition Between SN2 and SN1Reactions 8.9 The Role of the Solvent in SN2 and SN1 Reactions 8.10 Intermolecular Versus Intramolecular Reactions 8.11 Biological Methylating Reagents Have Good Leaving Groups 9 Elimination Reactions of Alkyl Halides * Competition between Substitution and Elimination 9.1 The E2 Reaction 9.2 An E2 Reaction is Regioselective 9.3 The E1 Reaction 9.4 Competition between E2 and E1 Reactions 9.5 E2 and E1 Reactions are Stereoselective 9.6 Elimination from Substituted Cyclohexanes 9.7 A Kinetic Isotope Effect Can Help Determine a Mechanism 9.8 Competition between Substitution and Elimination 9.9 Substitution and Elimination Reactions in Synthesis 9.10 Designing a Synthesis II: Approaching the Problem 10 Reactions of Alcohols, Ethers, Epoxides, Amine, and Sulfur- Containing Compounds 10.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides 10.2 Other Methods Used to Convert Alcohols into Alkyl Halides 10.3 Converting an Alcohol to a Sulfonate Ester 10.4 Elimination Reactions of Alcohols: Dehydration 10.5 Oxidation of Alcohols 10.6 Nucleophilic Substitution Reactions of Ethers 10.7 Nucleophilic Substitution Reactions of Epoxides 10.8 Amines Do Not Undergo Substitution or Elimination Reactions 10.9 Quaternary Ammonium Hydroxides Undergo Elimination Reactions 10.10 Phase-Transfer Catalysts 10.11 Thiols, Sulfides, and Sulfonium Salts 11 Organometallic Compounds 11.1 Organolithium and Organomagnesium Compounds 11.2 The Reaction Organolithium Compounds and Grighard Reagents with Electrophiles 11.3 Transmetallation 11.4 Coupling Reactions 11.5 Palladium-Catalyzed Coupling Reactions 11.6 Alkene Metathesis 12 Radicals * Reactions of Alkanes 12.1 Alkanes Are Unreactive Compounds 12.2 Chlorination and Bromination of Alkanes 12.3 Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron 12.4 The Distribution of Products Depends on Probability and Reactivity 12.5 The Reactivity-Selectivity Principle 12.6 Formation of Explosive Peroxides 12.7 The Addition of Radicals to an Alkene 12.8 The Stereochemistry of Radical Substitution and Addition Reactions 12.9 Radical Substitution of Benzylic and Allylic Hydrogens 12.10 Designing a Synthesis III: More Practice with Multistep Synthesis 12.11 Radical Reactions Occur in Biological Systems 12.12 Radicals and Stratospheric Ozone IV IDENTIFICATION OF ORGANIC COMPOUNDS 13 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy 13.1 Mass Spectrometry 13.2 The Mass Spectrum * Fragmentation 13.3 Isotopes in Mass Spectrometry 13.4 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas 13.5 Fragmentation Patterns of Functional Groups 13.6 Other Ionization Methods 13.7 Spectroscopy and the Electromagnetic Spectrum 13.8 Infrared Spectroscopy 13.9 Characteristic Infrared Absorption Bands 13.10 The Intensity of Absorption Bands 13.11 The Position of Absorption Bands 13.12 The Position of an Absorption Band is Affected by Electron Delocalization, Election Donation and Withdrawal, and Hydrogen Bonding 13.13 The Shape of Absorption Bands 13.14 The Absence of Absorption Bands 13.15 Some Vibrations Are Infrared Inactive 13.16 How to Interpret An Infrared Spectrum 13.17 Ultraviolet and Visible Spectroscopy 13.18 The Beer-Lambert Law 13.19 The Effect of Conjugation on max 13.20 The Visible Spectrum and Color 13.21 Some Uses of UV/Vis Spectroscopy 14 NMR Spectroscopy 14.1 An Introduction to NMR Spectroscopy 14.2 Fourier Transform NMR 14.3 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies 14.4 The Number of Signals in an 1H NMR Spectrum 14.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal 14.6 The Relative Positions of 1H NMR Signals 14.7 Characteristic Values of Chemical Shifts 14.8 Dismagnetic Anisotropy 14.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing the Signal 14.10 The Splitting of the Signals is Described by the N + 1 Rule 14.11 More Examples of 1H NMR Spectra 14.12 Coupling Constants Identify Coupled Protons 14.13 Splitting Diagrams Explain the Multiplicity of a Signal 14.14 Diastereotopic Hydrogens Are Not Chemically Equivalent 14.15 The Time Dependence of NMR Spectroscopy 14.16 Protons Bonded to Oxygen and Nitrogen 14.17 The Use of Deuterium in 1H NMR Spectroscopy 14.18 The Resolution of 1H NMR Spectra 14.19 13C NMR Spectroscopy 14.20 DEPT 13C NMR Spectra 14.21 Two-Dimensional NMR Spectroscopy 14.22 NMR Used in Medicine is Called Magnetic Resonance Imaging 14.23 X-Ray Crystallography V. AROMATIC COMPOUNDS 15 Aromaticity * Reactions of Benzene 15.1 Aromatic Compounds Are Unusually Stable 15.2 The Two Criteria for Aromaticity 15.3 Applying the Criteria for Aromaticity 15.4 Aromatic Heterocyclic Compounds 15.5 Some Chemical Consequences of Aromaticity 15.6 Antiaromaticity 15.7 A Molecular Orbital Description of Aromaticity and Antiaromaticity 15.8 The Nomenclature of Monosubstituted Benzenes 15.9 How Benzene Reacts 15.10 The General Mechanism for Electrophilic Aromatic Substitution Reactions 15.11 The Halogenation of Benzene 15.12 The Nitration of Benzene 15.13 The Sulfonation of Benzene 15.14 The Friedel-Crafts Acylation of Benzene 15.15 The Friedel-Crafts Alkylation of Benzene 15.16 The Alkylation of Benzene by Acylation-Reduction 15.17 Using Coupling Reactions to Alkylate Benzene 15.18 It Is Important to Have More Than One Way to Carry Out a Reaction 15.19 Polycyclic Benzold Hydrocarbons 15.20 Arene Oxides 16 Reactions of Substituted Benzenes 16.1 How Some Substituents on a Benzene Ring Can Be Chemically Changed 16.2 The Nomenclature of Disubstituted and Polysubstituted Benzenes 16.3 The Effect of Substituents on Reactivity 16.4 The Effect of Substituents on Orientation 16.5 The Effect of Substituents on pKa 16.6 The Ortho-Para Ratio 16.7 Additional Considerations Regarding Substituent Effects 16.8 Designing a Synthesis IV: Synthesis of Monosubstituted and Disubstituted Benzenes 16.9 The Synthesis of Trisubstituted Benzenes 16.10 The Synthesis of Substituted Benzenes Using Arenediazonium Salts 16.11 The Arenediazonium Ion as an Electrophile 16.12 The Mechanism for the Reaction of Amines with Nitrous Acid 16.13 Nucleophilic Aromatic Substitution: An Addition-Elimination Mechanism 16.14 Nucleophilic Aromatic Substitution: An Elimination-Addition Mechanism That Forms a Benzene VI. CARBONYL COMPOUNDS 17 Carbonyl Compounds I: Reactions of Carboxylic Acids and Carboxylic Derivatives 17.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives 17.2 The Structures of Carboxylic Acids and Carboxylic Derivatives 17.3 The Physical Properties of Carbonyl Compounds 17.4 Naturally Occurring Carboxylic Acids and Carboxylic Acid Derivatives 17.5 How Class I Carbonyl Compounds React 17.6 Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 17.7 General Mechanism for Nucleophilic Addition-Elimination Reactions 17.8 Reactions of Acyl Halides 17.9 Reactions of Acid Anhydrides 17.10 Reactions of Esters 17.11 Acid-Catalyzed Ester Hydrolysis and Transesterification 17.12 Hydroxide-Ion-Promoted Ester Hydrolysis 17.13 How the Mechanism for Nucleophilic Addition-Elimination was Confirmed 17.14 Soaps, Detergents, and Micelles 17.15 Reactions of Carboxylic Acids 17.16 Reactions of Amides 17.17 The Hydrolysis of Amides Is Catalyzed by Acids 17.18 The Hydrolysis of an Imide: A Way to Synthesize Primary Amines 17.19 The Hydrolysis of Nitriles 17.20 Designing a Synthesis V: The Synthesis of Cyclic Compounds 17.21 How Chemists Activate Carboxylic Acids 17.22 How Cells Activate Carboxylic Acids 17.23 Dicarboxylic Acids and Their Derivatives 18 Carbonyl Compounds II: Reactions of Aldehydes and Ketones * More Reactions of Carboxylic Acid Derivatives * Reactions of , - Unsaturated Carbonyl Compounds 18.1 The Nomenclature of Aldehydes and Ketones 18.2 The Relative Reactivities of Carbonyl Compounds 18.3 How Aldehydes and Ketones React 18.4 The Reactions of Carbonyl Compounds with Gringard Reagents 18.5 The Reactions of Carbonyl Compounds with Acetylide Ions 18.6 The Reactions of Carbonyl Compounds with Hydride Ion 18.7 The Reactions of Aldehydes and Ketones with Hydrogen Cyanide 18.8 The Reactions of Aldehydes and Ketones with Amines and Amine Derivatives 18.9 The Reactions of Aldehydes and Ketones with Water 18.10 Reactions of Aldehydes and Ketones with Alcohols 18.11 Protecting Groups 18.12 Addition of Sulfur Nucleophiles 18.13 The Wittig Reaction Forms an Alkene 18.14 Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces 18.15 Designing a Synthesis VI: Disconnections, Synthons, and Synthetic Equivalents 18.16 Nucleophilic Addition to , - Unsaturated Aldehydes and Ketones 18.17 Nucleophilic Addition to , - Unsaturated Carboxylic Acid Derivatives 18.18 Enzyme-Catalyzed Additions to , - Unsaturated Carbonyl Compounds 19 Carbonyl Compounds III: Reactions at the - Carbon 19.1 The Acidity of an - Hydrogen 19.2 Keto-Enol Tautomers 19.3 Keto-Enol Interconversion 19.4 How Enolate Ions and Enols 19.5 Halogenation of the - Carbon and Aldehydes and Ketones 19.6 Halogenation of the - Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction 19.7 - Halogenated Carbonyl Compounds Are Useful in Synthesis 19.8 Using LDA to Form an Enolate Ion 19.9 Alkylating the -Carbon of Carbonyl Compounds 19.10 Alkylation and Acylation of the -Carbon Using an Enamine Intermediate 19.11 Alkylation of the -Carbon: The Michael Reaction 19.12 An Aldol Addition Forms -Hydroxaldehydes or -Hydroxyketones 19.13 Dehydration of Aldol Addition Products Form , -Unsaturated Aldehydes and Ketones 19.14 The Crossed Aldol Addition 19.15 A Claisen Condensation Forms a -Keto Ester 19.16 Other Crossen Condensations 19.17 Intramolecular Condensation and Addition Reactions 19.18 The Robinson Annulation 19.19 Carboxylic Acids with a Carbonyl Group at the 3-Position can be Decarboxylated 19.20 The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid 19.21 The Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone 19.22 Designing a Synthesis VII: Making New Carbon-Carbon Bonds 19.23 Reactions at the -Carbon in Biological Systems VII MORE ABOUT OXIDATION-REDUCTION REACTIONS AND AMINES 20 More About Oxidation-Reduction Reactions 20.1 Oxidation-Reduction Reactions of Organic Compounds: An Overview 20.2 Reduction Reactions 20.3 Chemoselective Reactions 20.4 Oxidation of Alcohols 20.5 Oxidation of Aldehydes and Ketones 20.6 Designing a Synthesis VIII: Controlling Stereochemistry 20.7 Oxidation of Alkenes to 1,2 Diols 20.8 Oxidative Cleavage of 1,2 Diols 20.9 Oxidative Cleavage of Alkenes 20.10 Designing a Synthesis IX: Functional Group Interconversion 21 More About Amines * Heterocylic Compounds 21.1 More about Amine Nomenclature 21.2 More About the Acid-Base Properties of Amines 21.3 Amines React as Bases and as Nucleophiles 21.4 Synthesis of Amines 21.5 Aromatic Five-Membered-Ring Heterocycles 21.6 Aromatic Six-Membered-Ring Heterocycles 21.7 Amine Heterocycles Have Important Roles in Nature VIII BIOORGANIC COMPOUNDS 22 The Organic Chemistry of Carbohydrates 22.1 Classification of Carbohydrates 22.2 The D and L Notation 22.3 The Configurations of Aldoses 22.4 The Configurations of Ketoses 22.5 The Reactions of Monosaccharides in Basic Solutions 22.6 The Oxidation-Reduction Reactions of Monosaccharides 22.7 Monosaccharides Form Crystalline Osazones 22.8 Lengthening the Chain: The Kiliani-Fischer Synthesis 22.9 Shortening the Chain: The Wohl Degradation 22.10 The Stereochemistry of Glucose: The Fischer Proof 22.11 Monosaccharides Form Cyclic Hemiacetals 22.12 Glucose is the Most Stable Aldohexose 22.13 Formation of Glycosides 22.14 The Anomeric Effect 22.15 Reducing and Nonreducing Sugars 22.16 Disaccharides 22.17 Polysaccharides 22.18 Some Naturally Occurring Products Derived from Carbohydrates 22.19 Carbohydrates on Cell Surfaces 22.20 Synthetic Sweeteners 23 The Organic Chemistry of Amino Acids, Peptides, and Proteins 23.1 Classification and Nomenclature of Amino Acids 23.2 The Configuration of the Amino Acids 23.3 The Acid-Base Properties of Amino Acids 23.4 The Isoelectric Point 23.5 Separating Amino Acids 23.6 The Synthesis of Amino Acids 23.7 The Resolution of Racemic Mixtures of Amino Acids 23.8 Peptide Bonds and Disulfide Bonds 23.9 Some Interesting Peptides 23.10 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation 23.11 Automated Peptide Synthesis 23.12 An Introduction to Protein Structure 23.13 How to Determine the Primary Structure of a Polypeptide or Protein 23.14 The Secondary Structure of Proteins 23.15 The Tertiary Structure of Proteins 23.16 The Quaternary Structure of Proteins 23.17 Protein Denaturation 24 Catalysis 24.1 Catalysis in Organic Reactions 24.2 Acid Catalysis 24.3 Base Catalysis 24.4 Nucleophilic Catalysis 24.5 Metal-Ion Catalysis 24.6 Intramolecular Reactions 24.7 Intramolecular Catalysis 24.8 Catalysis in Biological Reactions 24.9 Enzyme-Catalyzed Reactions 24.10 The Organic Mechanisms of the Coenzymes 25 Compounds Derived from Vitamins 25.1 The Vitamin Needed for Many Redox Reactions: Vitamin B3 25.2 Flavin Adenine Dinucleotide and Flavin Mononucleotind: Vitamin B 25.3 Thiamine Pyrophosphate: Vitamin B1 25.4 Biotin: Vitamin H 25.5 Pyridoxal Phosphate: Vitamin B6 25.6 Coenzyme B12: Vitamin B12 25.7 Tetrahydrofolate: Folic Acid 25.8 Vitamin KH2: Vitamin K 26 The Organic Chemistry of Metabolic Pathways 26.1 ATP is Used for Phosphoryl Transfer Reactions 26.2 The Three Mechanisms for Phosphoryl Transfer Reactions 26.3 The "High-Energy" Character of Phosphoanhydride Bonds 26.4 Why ATP is Kinetically Stable in a Cell 26.5 The Four Stages of Catabolism 26.6 The Catabolism of Fats 26.7 The Catabolism of Carbohydrates 26.8 The Fates of Pyruvate 26.9 The Catabolism of Proteins 26.10 The Citric Acid Cycle 26.11 Oxidative Phosphorylation 26.12 Anabolism 27 The Organic Chemistry of Lipids 27.1 Fatty Acids Are Long-Chain Carboxylic Acids 27.2 Waxes are High-Molecular-Weight Esters 27.3 Fats and Oils are Triacylclycerols 27.4 Phospholipids and Sphingolipids Are Components of Membranes 27.5 Prostaglandis Regulate Physiological Responses 27.6 Terpenes Contain Carbon Atoms in Multiples of Five 27.7 How Terpenes Are Biosynthesized 27.8 How Steriods Are Chemical Messengers 27.9 How Nature Synthesizes Cholesterol 27.10 Synthetic Steroids 28 The Chemistry of Nucleic Acids 28.1 Nucleosides and Nucleotides 28.2 Other Important Nucleotides 28.3 Nucleic Acids Are Composed of Nucleotide Subunits 28.4 Why DNA Does Not Have A 2'- OH Group 28.5 The Biosynthesis of DNA is Called Replication 28.6 DNA and Heredity 28.7 The Biosynthesis of RNA is Called Transcription 28.8 There Are Three Kinds of RNA 28.9 The Biosynthesis of Proteins Is Called Translation 28.10 Why DNA Contains Thymine Instead of Uracil 28.11 How the Base Sequence of DNA Is Determined 28.12 The Polymerase Chain Reaction (PCR) 28.13 Genetic Engineering 28.14 The Laboratory Synthesis of DNA Strands IX SPECIAL TOPICS IN ORGANIC CHEMISTRY 29 Synthetic Polymers 29.1 There Are Two Major Classes of Synthetic Polymers 29.2 Chain-Growth Polymers 29.3 Stereochemistry of Polymerization * Ziegler- Natta Catalysts 29.4 Polymerization of Dienes * The Manufacture of Rubber 29.5 Copolymers 29.6 Step-Growth Polymers 29.7 Classes of Step-Growth Polymers 29.8 Physical Properties of Polymers 29.9 Biodegradable Polymers 30 Pericyclic Reactions 30.1 There Are Three Kinds of Pericyclic Reactions 30.2 Molecular Orbitals and Orbital Symmetry 30.3 Electrocyclic Reactions 30.4 Cycloaddition Reactions 30.5 Sigmatropic Rearrangements 30.6 Pericyclic Reactions in Biological Systems 30.7 Summary of the Selection Rules for Pericyclic Reactions 31 The Organic Chemistry of Drugs: Discovery and Design 31.1 Naming Drugs 31.2 Lead Compounds 31.3 Molecular Modification 31.4 Random Screening 31.5 Serendipity in Drug Development 31.6 Receptors 31.7 Drugs as Enzyme Inhibitors 31.8 Designing a Suicide Substrate 31.9 Quantitative Structure-Activity Relationships (QSAR) 31.10 Molecular Modeling 31.11 Combinatorial Organic Synthesis 31.12 Antiviral Drugs 31.13 Economics of Drugs * Governmental Regulations

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