pt. 1 INTRODUCTION TO THE STUDY OF ORGANIC CHEMISTRY -- 1. Remembering General Chemistry: Electronic Structure and Bonding -- 1.1. 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 -- Problem-Solving Strategy -- 1.5. Atomic Orbitals -- 1.6. 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. Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion -- 1.11. Bonds in Ammonia and in the Ammonium Ion -- 1.12. Bonds in Water -- 1.13. Bond in a Hydrogen Halide -- 1.14. Hybridization and Molecular Geometry -- Problem-Solving Strategy -- 1.15. Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles -- Problem-Solving Strategy -- 1.16. Dipole Moments of Molecules -- Some Important Things to Remember -- Problems -- 2. Acids and Bases: Central to Understanding Organic Chemistry -- 2.1. Introduction to Acids and Bases -- 2.2. pKa and pH -- Problem-Solving Strategy -- 2.3. Organic Acids and Bases -- Problem-Solving Strategy -- 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 Substituents Affect the Strength of an Acid -- Problem-Solving Strategy -- 2.8. Introduction to Delocalized Electrons -- 2.9. Summary of the Factors that Determine Acid Strength -- 2.10. How pH Affects the Structure of an Organic Compound -- Problem-Solving Strategy -- 2.11. Buffer Solutions -- 2.12. Lewis Acids and Bases -- Some Important Things to Remember -- Problems -- Tutorial Acids and Bases -- 3. Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure -- 3.1. How Alkyl Substituents Are Named -- 3.2. Nomenclature of Alkanes -- 3.3. Nomenclature of Cycloalkanes Skeletal Structures -- Problem-Solving Strategy -- 3.4. Nomenclature of Alkyl Halides -- 3.5. Nomenclature of Ethers -- 3.6. Nomenclature of Alcohols -- 3.7. Nomenclature of Amines -- 3.8. Structures of Alkyl Halides, Alcohols, Ethers, and Amines -- 3.9. Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines -- Problem-Solving Strategy -- 3.10. Rotation Occurs About Carbon-Carbon Single Bonds -- 3.11. Some Cycloalkanes Have Angle Strain -- Problem-Solving Strategy -- 3.12. Conformers of Cyclohexane -- 3.13. Conformers of Monosubstituted Cyclohexanes -- Problem-Solving Strategy -- 3.14. Conformers of Disubstituted Cyclohexanes -- 3.15. Fused Cyclohexane Rings -- Some Important Things to Remember -- Problems -- pt. 2 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. Chiral Object Has a Nonsuperimposable Mirror Image -- 4.3. 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 -- Problem-Solving Strategy -- Problem-Solving Strategy -- 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 -- Problem-Solving Strategy -- 4.13. Meso Compounds Have Asymmetric Centers but Are Optically Inactive -- Problem-Solving Strategy -- 4.14. How to Name Isomers with More than One Asymmetric Center -- Problem-Solving Strategy -- 4.15. How Enantiomers Can Be Separated -- 4.16. Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers -- Some Important Things to Remember -- Problems -- 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. Nomenclature of Alkenes -- 5.3. Structure of Alkenes -- 5.4. Naming Alkenes Using the E,Z System -- Problem-Solving Strategy -- Problem-Solving Strategy -- 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. Rate of a Chemical Reaction -- 5.9. Difference Between the Rate of a Reaction and the Rate Constant for a Reaction -- 5.10. Reaction Coordinate Diagram Describes the Energy Changes that Take Place during a Reaction -- 5.11. Catalysis -- 5.12. Catalysis by Enzymes -- Some Important Things to Remember -- Problems -- Tutorial an Exercise in Drawing Curved Arrows: Pushing Electrons -- 6. Reactions of Alkenes The Stereochemistry of Addition Reactions -- 6.1. 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 -- Problem-Solving Strategy -- 6.5. Addition of Water to an Alkene -- 6.6. Addition of an Alcohol to an Alkene -- 6.7. Carbocation Will Rearrange if it Can Form a More Stable Carbocation -- 6.8. Addition of Borane to an Alkene: Hydroboration-Oxidation -- 6.9. Addition of a Halogen to an Alkene -- Problem-Solving Strategy -- 6.10. Addition of a Peroxyacid to an Alkene -- 6.11. Addition of Ozone to an Alkene: Ozonolysis -- Problem-Solving Strategy -- 6.12. Addition of Hydrogen to an Alkene -- Problem-Solving Strategy -- 6.13. Relative Stabilities of Alkenes -- 6.14. Regioselective, Stereoselective, and Stereospecific Reactions -- 6.15. Stereochemistry of Electrophilic Addition Reactions of Alkenes -- Problem-Solving Strategy -- 6.16. Stereochemistry of Enzyme-Catalyzed Reactions -- 6.17. Enantiomers Can Be Distinguished by Biological Molecules -- 6.18. Reactions and Synthesis -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 7. Reactions of Alkynes An Introduction to Multistep Synthesis -- 7.1. Nomenclature of Alkynes -- 7.2. How to Name a Compound That Has More than One Functional Group -- 7.3. Physical Properties of Unsaturated Hydrocarbons -- 7.4. Structure of Alkynes -- 7.5. Alkynes Are Less Reactive than Alkenes -- 7.6. Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne -- 7.7. Addition of Water to an Alkyne -- 7.8. Addition of Borane to an Alkyne: Hydroboration-Oxidation -- 7.9. Addition of Hydrogen to an Alkyne -- 7.10. Hydrogen Bonded to an sp Carbon Is "Acidic" -- Problem-Solving Strategy -- 7.11. Synthesis Using Acetylide Ions -- 7.12. Introduction to Multistep Synthesis -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 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. Bonding in Benzene -- 8.3. Resonance Contributors and the Resonance Hybrid -- 8.4. How to Draw Resonance Contributors -- 8.5. Predicted Stabilities of Resonance Contributors -- 8.6. Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound -- Problem-Solving Strategy -- 8.7. Benzene Is an Aromatic Compound -- 8.8. Two Criteria for Aromaticity -- 8.9. Applying the Criteria for Aromaticity -- Problem-Solving Strategy -- 8.10. Aromatic Heterocyclic Compounds -- 8.11. Antiaromaticity -- 8.12. Molecular Orbital Description of Aromaticity and Antiaromaticity -- 8.13. More Examples that Show How Delocalized Electrons Increase Stability -- 8.14. Molecular Orbital Description of Stability -- 8.15. How Delocalized Electrons Affect pKa Values -- Problem-Solving Strategy -- 8.16. Delocalized Electrons Can Affect the Product of a Reaction -- 8.17. Reactions of Dienes -- 8.18. Thermodynamic versus Kinetic Control -- 8.19. 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 -- Some Important Things to Remember -- Summary of Reactions -- Problems -- Tutorial Drawing Resonance Contributors -- pt. 3 SUBSTITUTION AND ELIMINATION REACTIONS -- 9. Substitution Reactions of Alkyl Halides -- 9.1. Mechanism for an SN2 Reaction -- 9.2. Factors that Affect SN2 Reactions -- 9.3. Mechanism for an SN1 Reaction -- 9.4. Factors that Affect SN1 Reactions -- 9.5. Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides -- Problem-Solving Strategy -- 9.6. Competition Between SN2 and SN1 Reactions -- Problem-Solving Strategy -- 9.7. Role of the Solvent in SN1 and SN2 Reactions -- 9.8. Intermolecular versus Intramolecular Reactions -- Problem-Solving Strategy -- 9.9. Methylating Agents Used by Chemists versus Those Used by Cells -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 10. Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination -- 10.1. E2 Reaction -- 10.2. E2 Reaction Is Regioselective -- 10.3. E1 Reaction -- Problem-Solving Strategy -- 10.4. Benzylic and Allylic Halides -- 10.5. Competition Between E2 and E1 Reactions --

Contents note continued: 10.6. E2 and E1 Reactions Are Stereoselective -- Problem-Solving Strategy -- 10.7. Elimination from Substituted Cyclohexanes -- 10.8. 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. Approaching the Problem -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 11. Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols -- 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 -- Problem-Solving Strategy -- 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 -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 12. Organometallic Compounds -- 12.1. Organolithium and Organomagnesium Compounds -- 12.2. Transmetallation -- 12.3. Organocuprates -- 12.4. Palladium-Catalyzed Coupling Reactions -- Problem-Solving Strategy -- 12.5. Alkene Metathesis -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 13. Radicals Reactions of Alkanes -- 13.1. Alkanes Are Unreactive Compounds -- 13.2. 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. Distribution of Products Depends On Probability and Reactivity -- 13.5. Reactivity-Selectivity Principle -- Problem-Solving Strategy -- 13.6. Formation of Explosive Peroxides -- 13.7. Addition of Radicals to an Alkene -- 13.8. Stereochemistry of Radical Substitution and Radical Addition Reactions -- 13.9. Radical Substitution of Benzylic and Allylic Hydrogens -- 13.10. More Practice With Multistep Synthesis -- 13.11. Radical Reactions Occur In Biological Systems -- 13.12. Radicals and Stratospheric Ozone -- Some Important Things to Remember -- Summary of Reactions -- Problems -- Tutorial Drawing Curved Arrows in Radical Systems -- pt. 4 IDENTIFICATION OF ORGANIC COMPOUNDS -- 14. Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/Visible Spectroscopy -- 14.1. Mass Spectrometry -- 14.2. Mass Spectrum Fragmentation -- 14.3. Using the m/z Value of the Molecular Ion to Calculate the Molecular Formula -- Problem-Solving Strategy -- 14.4. Isotopes in Mass Spectrometry -- 14.5. High-Resolution Mass Spectrometry Can Reveal Molecular Formulas -- 14.6. 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. Intensity of Absorption Bands -- 14.13. Position of Absorption Bands -- 14.14. Position and Shape of an Absorption Band Is Affected By Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding -- Problem-Solving Strategy -- 14.15. 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. Beer-Lambert Law -- 14.20. Effect of Conjugation on λmax -- 14.21. Visible Spectrum and Color -- 14.22. Some Uses of UV/VIS Spectroscopy -- Some Important Things to Remember -- Problems -- 15. NMR Spectroscopy -- 15.1. Introduction to NMR Spectroscopy -- 15.2. Fourier Transform NMR -- 15.3. Shielding Causes Different Hydrogens to Show Signals at Different Frequencies -- 15.4. Number of Signals in an 1H NMR Spectrum -- Problem-Solving Strategy -- 15.5. Chemical Shift Tells How Far the Signal Is from the Reference Signal -- 15.6. Relative Positions of 1H NMR Signals -- 15.7. Characteristic Values of Chemical Shifts -- 15.8. Diamagnetic Anisotropy -- 15.9. Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal -- 15.10. 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 -- Problem-Solving Strategy -- 15.14. Splitting Diagrams Explain the Multiplicity of a Signal -- 15.15. Diastereotopic Hydrogens are Not Chemically Equivalent -- 15.16. Time Dependence of NMR Spectroscopy -- 15.17. Protons Bonded To Oxygen and Nitrogen -- 15.18. Use of Deuterium in 1H NMR Spectroscopy -- 15.19. Resolution of 1H NMR Spectra -- 15.20. 13C NMR Spectroscopy -- Problem-Solving Strategy -- 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 -- Some Important Things to Remember -- Problems -- pt. 5 CARBONYL COMPOUNDS -- 16. Reactions of Carboxylic Acids and Carboxylic Derivatives -- 16.1. Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives -- 16.2. Structures of Carboxylic Acids and Carboxylic Acid Derivatives -- 16.3. Physical Properties of Carbonyl Compounds -- 16.4. Fatty Acids Are Long-Chain Carboxylic Acids -- 16.5. How Carboxylic Acids and Carboxylic Acid Derivatives React -- Problem-Solving Strategy -- 16.6. Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives -- 16.7. General Mechanism for Nucleophilic Addition-Elimination Reactions -- 16.8. Reactions of Acyl Chlorides -- 16.9. 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 -- Problem-Solving Strategy -- 16.15. Reactions of Amides -- 16.16. Acid-Catalyzed Amide Hydrolysis and Alcoholysis -- 16.17. Hydroxide-Ion Promoted Hydrolysis of Amides -- 16.18. 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 -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 17. Reactions of Aldehydes and Ketones More Reactions of Carboxylic Acid Derivatives Reactions of α,β-Unsaturated Carbonyl Compounds -- 17.1. Nomenclature of Aldehydes and Ketones -- 17.2. Relative Reactivities of Carbonyl Compounds -- 17.3. How Aldehydes and Ketones React -- 17.4. Reactions of Carbonyl Compounds with Gringard Reagents -- Problem-Solving Strategy -- 17.5. Reactions of Carbonyl Compounds with Acetylide Ions -- 17.6. Reactions of Aldehydes and Ketones with Cyanide Ion -- 17.7. Reactions of Carbonyl Compounds with Hydride Ion -- 17.8. More About Reduction Reactions -- 17.9. Chemoselective Reactions -- 17.10. Reactions of Aldehydes and Ketones with Amines -- 17.11. Reactions of Aldehydes and Ketones with Water -- 17.12. Reactions of Aldehydes and Ketones with Alcohols -- Problem-Solving Strategy -- 17.13. Protecting Groups -- 17.14. Addition of Sulfur Nucleophiles -- 17.15. Reactions of Aldehydes and Ketones with a Peroxyacid -- 17.16. Wittig Reaction Forms an Alkene -- 17.17. Disconnections, Synthons, and Synthetic Equivalents -- 17.18. Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones -- 17.19. Nucleophilic Addition to α,β-Unsaturated Carboxylic Acid Derivatives -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 18. Reactions at the α-Carbon of Carbonyl Compounds -- 18.1. Acidity of an α-Hydrogen -- Problem-Solving Strategy -- 18.2. Keto-Enol Tautomers -- 18.3. Keto-Enol Interconversion -- 18.4. Halogenation of the α-Carbon of Aldehydes and Ketones -- 18.5. Halogenation of the α-Carbon of Carboxylic Acids: The Hell--Volhard--Zelinski Reaction -- 18.6. Forming an Enolate Ion -- 18.7. Alkylating the α-Carbon of Carbonyl Compounds -- Problem-Solving Strategy -- 18.8. Alkylating and Acylating the α-Carbon Using an Enamine Intermediate -- 18.9. Alkylating the β-Carbon: The Michael Reaction -- 18.10. Aldol Addition Forms β-Hydroxyaldehydes or β-Hydroxyketones -- 18.11. Dehydration of Aldol Addition Products Forms α,β-Unsaturated Aldehydes and Ketones -- 18.12. Crossed Aldol Addition -- 18.13. Claisen Condensation Forms a β-Keto Ester -- 18.14. Other Crossed Condensations -- 18.15. Intramolecular Condensations and Intramolecular Aldol Additions -- 18.16. Robinson Annulation -- Problem-Solving Strategy -- 18.17. Carboxylic Acids with a Carbonyl Group at the 3-Position Can Be Decarboxylated -- 18.18. Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid -- 18.19. Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone -- 18.20. Making New Carbon-Carbon Bonds -- 18.21. Reactions at the α-Carbon in Living Systems -- 18.22. Organizing What We Know About the Reactions of Organic Compounds --

Contents note continued: Some Important Things to Remember -- Summary of Reactions -- Problems -- pt. 6 AROMATIC COMPOUNDS -- 19. Reactions of Benzene and Substituted Benzenes -- 19.1. Nomenclature of Monosubstituted Benzenes -- 19.2. How Benzene Reacts -- 19.3. General Mechanism for Electrophilic Aromatic Substitution Reactions -- 19.4. Halogenation of Benzene -- 19.5. Nitration of Benzene -- 19.6. Sulfonation of Benzene -- 19.7. Friedel-Crafts Acylation of Benzene -- 19.8. Friedel-Crafts Alkylation of Benzene -- 19.9. 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. Nomenclature of Disubstituted and Polysubstituted Benzenes -- 19.14. Effect of Substituents on Reactivity -- 19.15. Effect of Substituents on Orientation -- 19.16. Effect of Substituents on p/Ca -- Problem-Solving Strategy -- 19.17. Ortho-Para Ratio -- 19.18. Additional Considerations Regarding Substituent Effects -- 19.19. Synthesis of Monosubstituted and Disubstituted Benzenes -- 19.20. Synthesis of Trisubstituted Benzenes -- 19.21. Synthesis of Substituted Benzenes Using Arenediazonium Salts -- 19.22. Arenediazonium Ion as an Electrophile -- 19.23. Mechanism for the Reaction of Amines with Nitrous Acid -- 19.24. Nucleophilic Aromatic Substitution: An Addition-Elimination Reaction -- 19.25. Synthesis of Cyclic Compounds -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 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. Synthesis of Amines -- 20.5. Aromatic Five-Membered-Ring Heterocycles -- 20.6. Aromatic Six-Membered-Ring Heterocycles -- Problem-Solving Strategy -- 20.7. Some Amine Heterocycles Have Important Roles in Nature -- 20.8. Organizing What We Know About the Reactions of Organic Compounds -- Some Important Things to Remember -- Summary of Reactions -- Problems -- pt. 7 BIOORGANIC COMPOUNDS -- 21. Organic Chemistry of Carbohydrates -- 21.1. Classification of Carbohydrates -- 21.2. d and l Notation -- 21.3. Configurations of the Aldoses -- 21.4. Configurations of the Ketoses -- 21.5. Reactions of Monosaccharides in Basic Solutions -- 21.6. Oxidation-Reduction Reactions of Monosaccharides -- 21.7. Lengthening the Chain: The Kiliani---Fischer Synthesis -- 21.8. Shortening the Chain: The Wohl Degradation -- 21.9. 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. Anomeric Effect -- 21.14. Reducing and Nonreducing Sugars -- 21.15. Disaccharides -- 21.16. Polysaccharides -- 21.17. Some Naturally Occurring Compounds Derived from Carbohydrates -- 21.18. Carbohydrates on Cell Surfaces -- 21.19. Artificial Sweeteners -- Some Important Things to Remember -- Summary of Reactions -- Problems -- 22. Organic Chemistry of Amino Acids, Peptides, and Proteins -- 22.1. Nomenclature of Amino Acids -- 22.2. Configuration of Amino Acids -- 22.3. Acid-Base Properties of Amino Acids -- 22.4. Isoelectric Point -- 22.5. Separating Amino Acids -- 22.6. Synthesis of Amino Acids -- 22.7. Resolution of Racemic Mixtures of Amino Acids -- 22.8. Peptide Bonds and Disulfide Bonds -- 22.9. Some Interesting Peptides -- 22.10. Strategy of Peptide Bond Synthesis: N-Protection and C-Activation -- 22.11. Automated Peptide Synthesis -- 22.12. Introduction to Protein Structure -- 22.13. How to Determine the Primary Structure of a Polypeptide or Protein -- Problem-Solving Strategy -- 22.14. Secondary Structure -- 22.15. Tertiary Structure -- 22.16. Quaternary Structure -- 22.17. Protein Denaturation -- Some Important Things to Remember -- Problems -- 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. Mechanisms for Two Enzyme-Catalyzed Reactions that are Reminiscent of Acid-Catalyzed Amide Hydrolysis -- 23.10. Mechanism for an Enzyme-Catalyzed Reaction that Involves Two Sequential SN2 Reactions -- 23.11. Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of the Base-Catalyzed Enediol Rearrangement -- 23.12. Mechanism for an Enzyme-Catalyzed Reaction that Is Reminiscent of an Aldol Addition -- Some Important Things to Remember -- Problems -- 24. Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins -- 24.1. Niacin: The Vitamin Needed for Many Redox Reactions -- 24.2. Riboflavin: Another Vitamin Used in Redox Reactions -- 24.3. Vitamin B1: The Vitamin Needed for Acyl Group Transfer -- 24.4. Vitamin H: The Vitamin Needed for Carboxylation of an α-Carbon -- 24.5. Vitamin B6: The Vitamin Needed for Amino Acid Transformations -- 24.6. Vitamin B12: The Vitamin Needed for Certain Isomerizations -- 24.7. Folic Acid: The Vitamin Needed for One-Carbon Transfer -- 24.8. Vitamin K: The Vitamin Needed for Carboxylation of Glutamate -- Some Important Things to Remember -- Problems -- 25. 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. "High-Energy" Character of Phosphoanhydride Bonds -- 25.5. Four Stages of Catabolism -- 25.6. Catabolism of Fats -- 25.7. Catabolism of Carbohydrates -- Problem-Solving Strategy -- 25.8. Fate of Pyruvate -- 25.9. Catabolism of Proteins -- 25.10. 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 -- Problem-Solving Strategy -- 25.18. How Nature Synthesizes Cholesterol -- Some Important Things to Remember -- Problems -- 26. 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. Biosynthesis of DNA Is Called Replication -- 26.6. DNA and Heredity -- 26.7. Biosynthesis of RNA Is Called Transcription -- 26.8. RNAs Used for Protein Biosynthesis -- 26.9. Biosynthesis of Proteins Is Called Translation -- 26.10. Why DNA Contains Thymine Instead of Uracil -- 26.11. Antiviral Drugs -- 26.12. How the Base Sequence of DNA Is Determined -- 26.13. Polymerase Chain Reaction (PCR) -- 26.14. Genetic Engineering -- Some Important Things to Remember -- Problems -- pt. 8 SPECIAL TOPICS IN ORGANIC CHEMISTRY -- 27. Synthetic Polymers -- 27.1. There Are Two Major Classes of Synthetic 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 -- Some Important Things to Remember -- Problems -- 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 -- Some Important Things to Remember -- Problems -- APPENDICES -- I. pKa Values -- II. Kinetics -- III. Summary of Methods Used to Synthesize a Particular Functional Group -- IV. Summary of Methods Employed to Form Carbon-Carbon Bonds.