Part 1 An Introduction to the Study of Organic Chemistry 1 Remembering General Chemistry: Electronic Structure and Bonding 1.1 The Structure of an Atom 1.2 How the 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 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion 1.11 The Bonds in Ammonia and In the Ammonium Ion 1.12 The Bonds in Water 1.13 The Bond in a Hydrogen Halide 1.14 Hybridization and Molecular Geometry 1.15 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 1.16 The Dipole Moments of Molecules 2 Acids and Bases: Central to Understanding Organic Chemistry 2.1 An Introduction to Acids and Bases 2.2 pka and pH 2.3 Organic Acids and Bases 2.4 How to Predict the Outcome of an Acid—Base Reaction 2.5 How to Determine the Position of Equilibrium 2.6 How the Structure of an Acid affects its pKa Value 2.7 How Substituent’s affect the Strength of an Acid 2.8 An Introduction to Delocalized Electrons 2.9 A Summary of the Factors That Determine Acid Strength 2.10 How pH affects the Structure of an Organic Compound 2.11 Buffer Solutions 2.12 Lewis Acids and Bases Tutorial: Acids and Bases 3 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure 3.1 How Alkyl Substituents Are Named 3.2 The Nomenclature of Alkanes 3.3 The Nomenclature of Cycloalkanes • Skeletal Structures 3.4 The Nomenclature of Alkyl Halides 3.5 The Nomenclature of Ethers 3.6 The Nomenclature of Alcohols 3.7 The Nomenclature of Amines 3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 3.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines 3.10 Rotation Occurs about Carbon—Carbon single Bonds 3.11 Some Cycloalkanes Have Angle Strain 3.12 The Conformers of Cyclohexane 3.13 Conformers of Monosubstituted Cyclohexanes 3.14 Conformers of Disubstituted Cyclohexanes 3.15 Fused Cyclohexane Rings Part Two Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization Tutorial: Using Molecular Models 4 Isomers: The Arrangement of Atoms in Space 4.1 Cis—Trans Isomers Result from Restricted Rotation 4.2 A Chiral Object Has a Nonsuperimposable Mirror Image 4.3 An Asymmetric Center is a Cause of Chirality in a Molecule 4.4 Isomers with One Asymmetric Center 4.5 Asymmetric Centers and Stereocenters 4.6 How to Draw Enantiomers 4.7 Naming Enantiomers by the R, S System 4.8 Chiral Compounds Are Optically Active 4.9 How Specific Rotation Is Measured 4.10 Enantiomeric Excess 4.11 Compounds with More than One Asymmetric Center 4.12 Stereoisomers of Cyclic Compounds 4.13 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 4.14 How to Name Isomers with More than One Asymmetric Center 4.15 How Enantiomers Can be Separated 4.16 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers Tutorial: Interconverting Structural Representations 5 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics 5.1 Molecular Formulas and the Degree of Unsaturation 5.2 The Nomenclature of Alkenes 5.3 The Structure of Alkenes 5.4 Naming Alkenes Using the E,Z System 5.5 How an Organic Compound Reacts Depends On Its Functional Group 5.6 How Alkenes React • Curved Arrows Show the Flow of Electrons 5.7 Thermodynamics and Kinetics 5.8 The Rate of a Chemical Reaction 5.9 The Difference between the Rate of a Reaction and the Rate Constant for a Reaction 5.10 A Reaction Coordinate Diagram Describes the Energy Changes that Take Place during a Reaction 5.11 Catalysis 5.12 Catalysis by Enzymes Tutorial: An Exercise in Drawing Curved Arrows: Pushing Electrons 6 The Reactions of Alkenes: The Stereochemistry of Addition Reactions 6.1 The Addition of a Hydrogen Halide to an Alkene 6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon 6.3 What Does the Structure of the Transition State Look Like? 6.4 Electrophilic Addition Reactions Are Regioselective 6.5 The Addition of Water to an Alkene 6.6 The Addition of an Alcohol to an Alkene 6.7 A Carbocation will rearrange if it can Form a More Stable Carbocation 6.8 Oxymercuration—Demercuration Is another Way to Add Water to an Alkene 6.9 The Addition of Borane to an Alkene: Hydroboration—Oxidation 6.10 The Addition of a Halogen to an Alkene 6.11 The Addition of a Peroxyacid to an Alkene 6.12 The Addition Of Ozone To An Alkene: Ozonolysis 6.13 The Addition of Hydrogen to an Alkene 6.14 The Relative Stabilities of Alkenes 6.15 Regioselective, Stereoselective, and Stereospecific Reactions 6.16 The Stereochemistry of Electrophilic Addition Reactions of Alkenes 6.17 The Stereochemistry of Enzyme-Catalyzed Reactions 6.18 Enantiomers Can Be Distinguished by Biological Molecules 6.19 Reactions and Synthesis 7 The Reactions of Alkynes: An Introduction to Multistep Synthesis 7.1 The Nomenclature of Alkynes 7.2 How to Name a Compound That Has More than One Functional Group 7.3 The Physical Properties of Unsaturated Hydrocarbons 7.4 The Structure of Alkynes 7.5 Alkynes Are Less Reactive than Alkenes 7.6 The Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne 7.7 The Addition of Water to an Alkyne 7.8 The Addition of Borane to an Alkyne: Hydroboration—Oxidation 7.9 The Addition of Hydrogen to an Alkyne 7.10 A Hydrogen Bonded to an sp Carbon Is “Acidic” 7.11 Synthesis Using Acetylide Ions 7.12 Designing a Synthesis I: An Introduction to Multistep Synthesis 8 Delocalized Electrons and Their Effect on Stability, pKa, and the Products of a Reaction 8.1 Delocalized Electrons Explain Benzene’s Structure 8.2 The Bonding in Benzene 8.3 Resonance Contributors and the Resonance Hybrid 8.4 How to Draw Resonance Contributors 8.5 The Predicted Stabilities of Resonance Contributors 8.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound 8.7 Benzene is an Aromatic Compound 8.8 The Two Criteria for Aromaticity 8.9 Applying the Criteria for Aromaticity 8.10 Aromatic Heterocyclic Compounds 8.11 Antiaromaticity 8.12 A Molecular Orbital Description of Aromaticity and Antiaromaticity 8.13 More Examples that Show How Delocalized Electrons Affect Stability 8.14 A Molecular Orbital Description of Stability 8.15 How Delocalized Electrons Affect pKa Values 8.16 Delocalized Electrons Can Affect the Product of a Reaction 8.17 Reactions of Dienes 8.18 Thermodynamic Versus Kinetic Control 8.19 The Diels—Alder Reaction Is a 1,4-Addition Reaction 8.20 Retrosynthetic Analysis of the Diels—Alder Reaction 8.21 Organizing What We Know About the Reactions of Organic Compounds Tutorial: Drawing Resonance Contributors Part Three Substitution and Elimination Reactions 9 Substitution Reactions of Alkyl Halides 9.1 The Mechanism for an SN2 Reaction 9.2 Factors That Affect SN2 Reactions 9.3 The Mechanism for an SN1 Reaction 9.4 Factors That Affect SN1 Reactions 9.5 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides 9.6 Competition between SN2 and SN1 Reactions 9.7 The Role of the Solvent in SN1 and SN2 Reactions 9.8 Intermolecular Versus Intramolecular Reactions 9.9 Methylating Agents Used by Chemists Versus Those Used by Cells 10 Elimination Reactions of Alkyl Halides • Competition between Substitution and Elimination 10.1 The E2 Reaction 10.2 An E2 Reaction Is Regioselective 10.3 The E1 Reaction 10.4 Benzylic and Allylic Halides 10.5 Competition between E2 and E1 Reactions 10.6 E2 and E1 Reactions Are Stereoselective 10.7 Elimination from Substituted Cyclohexanes 10.8 A Kinetic Isotope Effect Can Help Determine a Mechanism 10.9 Competition between Substitution and Elimination 10.10 Substitution and Elimination Reactions in Synthesis 10.11 Designing a Synthesis II: Approaching the Problem 11 Reactions of Alcohols, Ethers, Amines, Thiols, and Thioethers 11.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides 11.2 Other Methods used to Convert Alcohols into Alkyl Halides 11.3 Converting an Alcohol into a Sulfonate Ester 11.4 Elimination Reactions of Alcohols: Dehydration 11.5 Oxidation of Alcohols 11.6 Nucleophilic Substitution Reactions of Ethers 11.7 Nucleophilic Substitution Reactions of Epoxides 11.8 Arene Oxides 11.9 Amines do not Undergo Substitution or Elimination Reactions 11.10 Quaternary Ammonium Hydroxides Undergo Elimination Reactions 11.11 Thiols, Sulfides, and Sulfonium Salts 11.12 Organizing What We Know About the Reactions of Organic Compounds 12 Organometallic Compounds 12.1 Organolithium and Organomagnesium Compounds 12.2 The Reaction of Organolithium Compounds And Gridnard Reagents With Electrophiles 12.3 Transmetallation 12.4 Coupling Reactions 12.5 Palladium-Catalyzed Coupling Reactions 12.6 Alkene Metathesis 13 Radicals • Reactions of Alkanes 13.1 Alkanes Are Unreactive Compounds 13.2 The Chlorination and Bromination of Alkanes 13.3 Radical Stability Depends On the Number of Alkyl Groups Attached To the Carbon with the Unpaired Electron 13.4 The Distribution of Products Depends On Probability and Reactivity 13.5 The Reactivity Selectivity Principle 13.6 Formation of Explosive Peroxides 13.7 The Addition of Radicals to an Alkene 13.8 The Stereochemistry of Radical Substitution and Radical Addition Reactions 13.9 Radical Substitution of Benzylic and Allylic Hydrogens 13.10 Designing a Synthesis III: More Practice with Multistep Synthesis 13.11 Radical Reactions Occur In Biological Systems 13.12 Radicals and Stratospheric Ozone Tutorial: Drawing Curved Arrows in Radical Systems Part Four Identification of Organic Compounds 14 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/ Visible Spectroscopy 14.1 Mass Spectrometry 14.2 The Mass Spectrum • Fragmentation 14.3 Using the m/z of the Molecular Ion to Calculate the Molecular Formula 14.4 Isotopes in Mass Spectrometry 14.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas 14.6 The Fragmentation Patterns of Functional Groups 14.7 Other Ionization Methods 14.8 Gas Chromatography–Mass Spectrometry 14.9 Spectroscopy and the Electromagnetic Spectrum 14.10 Infrared Spectroscopy 14.11 Characteristic Infrared Absorption Bands 14.12 The Intensity of Absorption Bands 14.13 The Position of Absorption Bands 14.14 The Position and Shape of an Absorption Band Is Affected By Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding 14.15 The Absence of Absorption Bands 14.16 Some Vibrations Are Infrared Inactive 14.17 How to Interpret an Infrared Spectrum 14.18 Ultraviolet and Visible Spectroscopy 14.19 The Beer- Lambert Law 14.20 The Effect of Conjugation on ?max 14.21 The Visible Spectrum and Color 14.22 Some Uses of UV/ VIS Spectroscopy 15 NMR Spectroscopy 15.1 An Introduction to NMR Spectroscopy 15.2 Fourier Transform NMR 15.3 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies 15.4 The Number of Signals in an 1H NMR Spectrum 15.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal 15.6 The Relative Positions of 1H NMR Signals 15.7 The Characteristic Values of Chemical Shifts 15.8 Diamagnetic Anisotropy 15.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal 15.10 The Splitting of Signals Is Described by the N 1 Rule 15.11 What causes Splitting? 15.12 More Examples of 1H NMR Spectra 15.13 Coupling Constants Identify Coupled Protons 15.14 Splitting Diagrams Explain the Multiplicity of a Signal 15.15 Diastereotopic Hydrogens Are Not Chemically Equivalent 15.16 The Time Dependence of NMR Spectroscopy 15.17 Protons Bonded to Oxygen and Nitrogen 15.18 The Use of Deuterium in 1H NMR Spectroscopy 15.19 The Resolution of 1H NMR Spectra 15.20 13C NMR Spectroscopy 15.21 Dept 13C NMR Spectra 15.22 Two-Dimensional NMR Spectroscopy 15.23 NMR Used in Medicine Is Called Magnetic Resonance Imaging 15.24 X-Ray Crystallography Part 5 Carbonyl Compounds 16 Reactions of Carboxylic Acids and Carboxylic Derivatives 16.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives 16.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives 16.3 The Physical Properties of Carbonyl Compounds 16.4 Fatty Acids Are Long-Chain Carboxylic Acids 16.5 How Carboxylic Acids and Carboxylic Acid Derivatives React 16.6 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 16.7 The General Mechanism for Nucleophilic Addition- Elimination Reactions 16.8 The Reactions of Acyl Chlorides 16.9 The Reactions of Esters 16.10 Acid-Catalyzed Ester Hydrolysis and Transesterification 16.11 Hydroxide-Ion-Promoted Ester Hydrolysis 16.12 How the Mechanism for Nucleophilic Addition-Elimination Was Confirmed 16.13 Fats and Oils are Triglycerides 16.14 Reactions of Carboxylic Acids 16.15 Reactions of Amides 16.16 Acid- Catalyzed Amide Hydrolysis and Alcoholysis 16.17 Hydroxide-Ion Promoted Hydrolysis of Amides 16.18 The Hydrolysis of an Imide: A Way to Synthesize Primary Amines 16.19 Nitriles 16.20 Acid Anhydrides 16.21 Dicarboxylic Acids 16.22 How Chemists Activate Carboxylic Acids 16.23 How Cells Activate Carboxylic Acids 17 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives • Reactions of a, ß- Unsaturated Carbonyl Compounds 17.1 The Nomenclature of Aldehydes and Ketones 17.2 The Relative Reactivities of Carbonyl Compounds 17.3 How Aldehydes and Ketones React 17.4 The Reactions of Carbonyl Compounds with Gringard Reagents 17.5 The Reactions of Carbonyl Compounds with Acetylide Ions 17.6 The Reactions of Aldehydes and Ketones with Cyanide Ion 17.7 The Reactions of Carbonyl Compounds with Hydride Ion 17.8 More about Reduction Reactions 17.9 Chemoselective Reactions 17.10 The Reactions of Aldehydes and Ketones with Amines 17.11 The Reactions of Aldehydes and Ketones with Water 17.12 The Reactions of Aldehydes and Ketones with Alcohols 17.13 Protecting Groups 17.14 The Addition of Sulfur Nucleophiles 17.15 The Reactions of Aldehydes and Ketones with a Peroxyacid 17.16 The Wittig Reaction Forms an Alkene 17.17 Designing a Synthesis IV: Disconnections, Synthons, and Synthetic Equivalents 17.18 Nucleophilic Addition to a, ß- Unsaturated Aldehydes and Ketones 17.19 Nucleophilic Addition to a, ß- Unsaturated Carboxylic Acid Derivatives 18 Reactions at the a- Carbon of Carbonyl Compounds 18.1 The Acidity of an a-Hydrogen 18.2 Keto-Enol Tautomers 18.3 Keto-Enol Interconversion 18.4 Halogenation of the a-Carbon of Aldehydes and Ketones. 18.5 Halogenation of the a-Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction 18.6 Forming an Enolate Ion 18.7 Alkylating the a-Carbon of Carbonyl Compounds 18.8 Alkylating the a-Carbon Using an Enamine Intermediate 18.9 Alkylating the ß-Carbon: The Michael Reaction 18.10 An Aldol Addition Forms ß-Hydroxyaldehydes or ß-Hydroxyketones 18.11 The Dehydration of Aldol Addition Products Forms a,ß-Unsaturated Aldehydes and Ketones 18.12 A Crossed Aldol Addition 18.13 A Claisen Condensation Forms a ß-Keto Ester 18.14 Other Crossed Condensations 18.15 Intramolecular Condensations And Intramolecular Aldol Additions 18.16 The Robinson Annulation 18.17 Carboxylic Acids with a Carbonyl Group at the 3-Position Can Be Decarboxylated 18.18 The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid 18.19 The Acetoacetic Ester Synthesis: A Way Synthesize a Methyl Ketone 18.20 Designing a Synthesis V: Making New Carbon-Carbon Bonds 18.21 Reactions at the a-Carbon in Biological Systems 18.22 Organizing What We Know About the Reactions of Organic Compounds Part 5 19 Reactions Of Benzene And Substituted Benzenes 19.1 The Nomenclature of Monosubstituted Benzenes 19.2 How Benzene Reacts 19.3 The General Mechanism for Electrophilic Aromatic Substitution Reactions 19.4 The Halogenation of Benzene 19.5 The Nitration of Benzene 19.6 The Sulfonation of Benzene 19.7 The Friedel-Crafts Acylation of Benzene 19.8 The Friedel-Crafts Alkylation of Benzene 19.9 The Alkylation of Benzene by Acylation-Reduction 19.10 Using Coupling Reactions to Alkylate Benzene 19.11 It Is Important to Have More than One Way to Carry Out a Reaction 19.12 How Some Substituents on a Benzene Ring Can Be Chemically Changed 19.13 The Nomenclature of Disubstituted and Polysubstituted Benzenes 19.14 The Effect of Substituents on Reactivity 19.15 The Effect of Substituents on Orientation 19.16 The Effect of Substituents on pKa 19.17 The Ortho/Para Ratio 19.18 Additional Considerations Regarding Substituent Effects 19.19 Designing a Synthesis VI: Synthesis of Monosubstituted and Disubstituted Benzenes 19.20 The Synthesis of Trisubstituted Benzenes 19.21 The Synthesis of Substituted Benzenes Using Arenediazonium Salts 19.22 The Arenediazonium Ion as an Electrophile 19.23 The Mechanism for the Reaction of Amines with Nitrous Acid 19.24 Nucleophilic Aromatic Substitution: An Addition-Elimination Reaction 19.25 Designing a Synthesis VII: The Synthesis of Cyclic Compounds Tutorial: Synthesis and Retrosynthetic Analysis 20 More About Amines· Reactions of Heterocyclic Compounds 20.1 More About Amine Nomenclature 20.2 More About the Acid-Base Properties of Amines 20.3 Amines React as Bases and as Nucleophiles 20.4 The Synthesis of Amines 20.5 Aromatic Five-Membered Ring Heterocycles 20.6 Aromatic Six-Membered-Ring Heterocycles 20.7 Some Amine Heterocycles Have Important Roles in Nature 20.8 Organizing What We Know About the Reactions of Organic Compounds Part 7: Bioorganic Compounds 21 The Organic Chemistry Of Carbohydrates 21.1 The Classification of Carbohydrates 21.2 The D and L Notation 21.3 The Configurations of the Aldoses 21.4 The Configurations of the Ketoses 21.5 The Reactions of Monosaccharides in Basic Solutions 21.6 The Oxidation-Reduction Reactions of Monosaccharides 21.7 Lengthening the Chain: The Kiliani—Fischer Synthesis 21.8 Shortening the Chain: The Wohl Degradation 21.9 The Stereochemistry of Glucose: The Fischer Proof 21.10 Monosaccharides Form Cyclic Hemiacetals 21.11 Glucose Is the Most Stable Aldohexose 21.12 Formation of Glycosides 21.13 The Anomeric Effect 21.14 Reducing and Nonreducing Sugars 21.15 Disaccharides 21.16 Polysaccharides 21.17 Some Naturally Occurring Products Derived from Carbohydrates 21.18 Carbohydrates on Cell Surfaces 21.19 Artificial Sweeteners 22 The Organic Chemistry Of Amino Acids, Peptides, And Proteins 22.1 Nomenclature of Amino Acids 22.2 The Configuration of the Amino Acids 22.3 The Acid-Base Properties of Amino Acids 22.4 The Isoelectric Point 22.5 Separating Amino Acids 22.6 The Synthesis of Amino Acids 22.7 The Resolution of Racemic Mixtures of Amino Acids 22.8 Peptide Bonds and Disulfide Bonds 22.9 Some Interesting Peptides 22.10 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation 22.11 Automated Peptide Synthesis 22.12 An Introduction to Protein Structure 22.13 How to Determine the Primary Structure of a Polypeptide or Protein 22.14 Secondary Structure 22.15 Tertiary Structure 22.16 Quaternary Structure 22.17 Protein Denaturation 23 Catalysis in Organic Reactions and in Enzymatic Reactions 23.1 Catalysis in Organic Reactions 23.2 Acid Catalysis 23.3 Base Catalysis 23.4 Nucleophilic Catalysis 23.5 Metal-Ion Catalysis 23.6 Intramolecular Reactions 23.7 Intramolecular Catalysis 23.8 Catalysis in Biological Reactions 23.9 The Mechanisms for Two Enzyme-Catalyzed Reactions That Are Reminiscent of Acid-Catalyzed Amide Hydrolysis 23.10 The Mechanism for an Enzyme-Catalyzed Reaction that Involves Two Sequential SN2 Reactions 23.11 The Mechanism for an Enzyme-Catalyzed Reaction that is Reminiscent of the Base-Catalyzed Enediol Rearrangement 23.12 The Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of the Aldol Addition Reaction 24 The Organic Chemistry Of The Coenzymes–Compounds Derived From Vitamins 24.1 The Vitamin Needed for Many Redox Reactions: Niacin 24.2 Another Vitamin Used in Redox Reactions: Riboflavin 24.3 The Vitamin Needed for Acyl Group Transfer: Vitamin B1 24.4 The Vitamin Needed for Carboxylation of an a-Carbon: Vitamin H 24.5 The Vitamin Needed for Amino Acid Transformations: Vitamin B6 24.6 The Vitamin Needed for Certain Isomerizations: Vitamin B12 24.7 The Vitamin Needed for One-Carbon Transfer: Folate 24.8 The Vitamin Needed for Carboxylation of Glutamate: Vitamin K 25 The Organic Chemistry of the Metabolic Pathways • Terpene Biosynthesis 25.1 ATP Is Used for Phosphoryl Transfer Reactions 25.2 ATP Activates A Compound by Giving it a Good Leaving Group 25.3 Why ATP Is Kinetically Stable in a Cell 25.4 The “High-Energy” Character of Phosphoanhydride Bonds 25.5 The Four Stages of Catabolism 25.6 The Catabolism of Fats 25.7 The Catabolism of Carbohydrates 25.8 The Fate of Pyruvate 25.9 The Catabolism of Proteins 25.10 The Citric Acid Cycle 25.11 Oxidative Phosphorylation 25.12 Anabolism 25.13 Gluconeogenesis 25.14 Regulating Metabolic Pathways 25.15 Amino Acid Biosynthesis 25.16 Terpenes Contain Carbon Atoms in Multiples of Five 25.17 How Terpenes Are Biosynthesized 25.18 How Nature Synthesizes Cholesterol 26 The Chemistry of the Nucleic Acids 26.1 Nucleosides and Nucleotides 26.2 Other Important Nucleotides 26.3 Nucleic Acids Are Composed of Nucleotide Subunits 26.4 Why DNA Does Not Have A 2’ —OH Group 26.5 The Biosynthesis of SNA Is Called Replication 26.6 DNA and Heredity 26.7 The Biosynthesis of RNA Is Called Transcription 26.8 There Are Three Kinds of RNA 26.9 The Biosynthesis of Proteins Is Called Translation 26.10 Why DNA Contains Thymine Instead of Uracil 26.11 Antiviral Drugs 26.12 The Polymerase Chain Reaction (PCR) 26.13 Genetic Engineering 26.14 The Laboratory Synthesis of DNA Strands Part 8 Special Topics in Organic Chemistry 27 Synthetic Polymers 27.1 There Are Two Major Classes of Syntheric Polymers 27.2 Chain-Growth Polymers 27.3 Stereochemistry of Polymerization • Ziegler-Natta Catalysts 27.4 Polymerization of Dienes • The Manufacture of Rubber 27.5 Copolymers 27.6 Step-Growth Polymers 27.7 Classes of Step-Growth Polymers 27.8 Physical Properties of Polymers 27.9 Recycling Polymers 27.10 Biodegradable Polymers 28 Pericyclic Reactions 28.1 There Are Three Kinds of Pericyclic Reactions 28.2 Molecular Orbitals and Orbital Symmetry 28.3 Electrocyclic Reactions 28.4 Cycloaddition Reactions 28.5 Sigmatropic Rearrangements 28.6 Pericyclic Reactions in Biological Systems 28.7 Summary of the Selection Rules for Pericyclic Reactions Appendix I Values Appendix II Derivations of Rate Laws Appendix III Summary of Methods Used to Synthesize a Particular Functional Group Appendix IV Summary of Methods Employed to Form Carbon-Carbon Bonds Answers to Selected Problems Glossary Photo Credits Index