Includes index.

Machine generated contents note: 1. Structure and Bonding -- 1-1. Atomic Structure: The Nucleus -- 1-2. Atomic Structure: Orbitals -- 1-3. Atomic Structure: Electron Configurations -- 1-4. Development of Chemical Bonding Theory -- 1-5. Describing Chemical Bonds: Valence Bond Theory -- 1-6. SP3 Hybrid Orbitals and the Structure of Methane -- 1-7. SP3 Hybrid Orbitals and the Structure of Ethane -- 1-8. SP2 Hybrid Orbitals and the Structure of Ethylene -- 1-9. SP Hybrid Orbitals and the Structure of Acetylene -- 1-10. Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur -- 1-11. Describing Chemical Bonds: Molecular Orbital Theory -- 1-12. Drawing Chemical Structures -- Something Extra Organic Foods: Risk versus Benefit -- 2. Polar Covalent Bonds; Acids and Bases -- 2-1. Polar Covalent Bonds: Electronegativity -- 2-2. Polar Covalent Bonds: Dipole Moments -- 2-3. Formal Charges -- 2-4. Resonance -- 2-5. Rules for Resonance Forms -- 2-6. Drawing Resonance Forms -- 2-7. Acids and Bases: The Brønsted-Lowry Definition -- 2-8. Acid and Base Strength -- 2-9. Predicting Acid-Base Reactions from pKa Values -- 2-10. Organic Acids and Organic Bases -- 2-11. Acids and Bases: The Lewis Definition -- 2-12. Noncovalent Interactions between Molecules -- Something Extra Alkaloids: From Cocaine to Dental Anesthetics -- 3. Organic Compounds: Alkanes and Their Stereochemistry -- 3-1. Functional Croups -- 3-2. Alkanes and Alkane Isomers -- 3-3. Alkyl Groups -- 3-4. Naming Alkanes -- 3-5. Properties of Alkanes -- 3-6. Conformations of Ethane -- 3-7. Conformations of Other Alkanes -- Something Extra Gasoline -- 4. Organic Compounds: Cycloalkanes and Their Stereochemistry -- 4-1. Naming Cycloalkanes -- 4-2. Cis-Trans Isomerism in Cycloalkanes -- 4-3. Stability of Cycloalkanes: Ring Strain -- 4-4. Conformations of Cycloalkanes -- 4-5. Conformations of Cyclohexane -- 4-6. Axial and Equatorial Bonds in Cyclohexane -- 4-7. Conformations of Monosubstituted Cyclohexanes -- 4-8. Conformations of Disubstituted Cyclohexanes -- 4-9. Conformations of Polycyclic Molecules -- Something Extra Molecular Mechanics -- 5. Stereochemistry at Tetrahedral Centers -- 5-1. Enantiomers and the Tetrahedral Carbon -- 5-2. Reason for Handedness in Molecules: Chirality -- 5-3. Optical Activity -- 5-4. Pasteur's Discovery of Enantiomers -- 5-5. Sequence Rules for Specifying Configuration -- 5-6. Diastereomers -- 5-7. Meso Compounds -- 5-8. Racemic Mixtures and the Resolution of Enantiomers -- 5-9. Review of Isomerism -- 5-10. Chirality at Nitrogen, Phosphorus, and Sulfur -- 5-11. Prochirality -- 5-12. Chirality in Nature and Chiral Environments -- Something Extra Chiral Drugs -- 6. Overview of Organic Reactions -- 6-1. Kinds of Organic Reactions -- 6-2. How Organic Reactions Occur: Mechanisms -- 6-3. Radical Reactions -- 6-4. Polar Reactions -- 6-5. Example of a Polar Reaction: Addition of H2O to Ethylene -- 6-6. Using Curved Arrows in Polar Reaction Mechanisms -- 6-7. Describing a Reaction: Equilibria, Rates, and Energy Changes -- 6-8. Describing a Reaction: Bond Dissociation Energies -- 6-9. Describing a Reaction: Energy Diagrams and Transition States -- 6-10. Describing a Reaction: Intermediates -- 6-11. Comparison between Biological Reactions and Laboratory Reactions -- Something Extra Where Do Drugs Come From? -- 7. Alkenes and Alkynes -- 7-1. Calculating the Degree of Unsaturation -- 7-2. Naming Alkenes and Alkynes -- 7-3. Cis-Trans Isomerism in Alkenes -- 7-4. Alkene Stereochemistry and the E,Z Designation -- 7-5. Stability of Alkenes -- 7-6. Electrophilic Addition Reactions of Alkenes -- Writing Organic Reactions -- 7-7. Orientation of Electrophilic Addition: Markovnikov's Rule -- 7-8. Carbocation Structure and Stability -- 7-9. Hammond Postulate -- 7-10. Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements -- Something Extra Terpenes: Naturally Occurring Alkenes -- 8. Reactions of Alkenes and Alkynes j -- 8-1. Preparing Alkenes: A Preview of Elimination Reactions -- 8-2. Halogenation of Alkenes -- 8-3. Halohydrins from Alkenes -- 8-4. Hydration of Alkenes -- 8-5. Reduction of Alkenes: Hydrogenation -- 8-6. Oxidation of Alkenes: Epoxidation -- 8-7. Oxidation of Alkenes: Hydroxylation -- 8-8. Oxidation of Alkenes: Cleavage to Carbonyl Compounds -- 8-9. Addition of Carbenes to Alkenes: Cyclopropane Synthesis -- 8-10. Radical Additions to Alkenes: Chain-Growth Polymers -- 8-11. Biological Additions of Radicals to Alkenes -- 8-12. Conjugated Dienes -- 8-13. Reactions of Conjugated Dienes -- 8-14. Diels-Alder Cycloaddition Reaction -- 8-15. Reactions of Alkynes -- Something Extra--Natural Rubber -- Learning Reactions -- 9. Aromatic Compounds -- 9-1. Naming Aromatic Compounds -- 9-2. Structure and Stability of Benzene -- 9-3. Aromaticity and the Huckel 4n + 2 Rule -- 9-4. Aromatic Ions and Aromatic Heterocycles -- 9-5. Polycyclic Aromatic Compounds -- 9-6. Reactions of Aromatic Compounds: Electrophilic Substitution -- 9-7. Alkylation and Acylation of Aromatic Rings: The Friedel--Crafts Reaction -- 9-8. Substituent Effects in Electrophilic Substitutions -- 9-9. Nucleophilic Aromatic Substitution -- 9-10. Oxidation and Reduction of Aromatic Compounds -- 9-11. Introduction to Organic Synthesis: Polysubstituted Benzenes -- Something Extra Aspirin, NSAIDs, and COX-2 Inhibitors -- 10. Structure Determination: Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet Spectroscopy -- 10-1. Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments -- 10-2. Interpreting Mass Spectra -- 10-3. Mass Spectrometry of Some Common Functional Groups -- 10-4. Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments -- 10-5. Spectroscopy and the Electromagnetic Spectrum -- 10-6. Infrared Spectroscopy -- 10-7. Interpreting Infrared Spectra -- 10-8. Infrared Spectra of Some Common Functional Groups -- 10-9. Ultraviolet Spectroscopy -- 10-10. Interpreting Ultraviolet Spectra: The Effect of Conjugation -- 10-11. Conjugation, Color, and the Chemistry of Vision -- Something Extra X-Ray Crystallography -- Structure Determination: Nuclear Magnetic Resonance Spectroscopy -- 11-1. Nuclear Magnetic Resonance Spectroscopy -- 11-2. Nature of NMR Absorptions -- 11-3. Chemical Shifts -- 11-4. 13C NMR Spectroscopy: Signal Averaging and FT-NMR -- 11-5. Characteristics of 13C NMR Spectroscopy -- 11-6. DEPT13C NMR Spectroscopy -- 11-7. Uses of 13C NMR Spectroscopy -- 11-8. NMR Spectroscopy and Proton Equivalence -- 11-9. Chemical Shifts in 1H NMR Spectroscopy -- 11-10. Integration of 1H NMR Absorptions: Proton Counting -- 11-11. Spin-Spin Splitting in 1H NMR Spectra -- 11-12. More Complex Spin-Spin Splitting Patterns -- 11-13. Uses of 1H NMR Spectroscopy -- Something Extra Magnetic Resonance Imaging (MRI) -- 12. Organohalides: Nucleophilic Substitutions and Eliminations -- 12-1. Names and Structures of Alkyl Halides -- 12-2. Preparing Alkyl Halides from Alkenes: Allylic Bromination -- 12-3. Preparing Alkyl Halides from Alcohols -- 12-4. Reactions of Alkyl Halides: Crignard Reagents -- 12-5. Organometallic Coupling Reactions -- 12-6. Discovery of the Nucleophilic Substitution Reaction -- 12-7. SN2 Reaction -- 12-8. Characteristics of the SN2 Reaction -- 12-9. SN1 Reaction -- 12-10. Characteristics of the SN1 Reaction -- 12-11. Biological Substitution Reactions -- 12-12. Elimination Reactions: Zaitsev's Rule -- 12-13. E2 Reaction and the Deuterium Isotope Effect -- 12-14. E1 and E1cB Reactions -- 12-15. Biological Elimination Reactions -- 12-16. Summary of Reactivity: SN1, SN2, E1, E1cB, and E2 -- Something Extra Naturally Occurring Organohalides -- 13. Alcohols, Phenols, and Thiols; Ethers and Sulfides -- 13-1. Naming Alcohols, Phenols, and Thiols -- 13-2. Properties of Alcohols, Phenols, and Thiols -- 13-3. Preparing Alcohols from Carbonyl Compounds -- 13-4. Reactions of Alcohols -- 13-5. Oxidation of Alcohols and Phenols -- 13-6. Protection of Alcohols -- 13-7. Preparation and Reactions of Thiols -- 13-8. Ethers and Sulfides -- 13-9. Preparing Ethers -- 13-10. Reactions of Ethers -- 13-11. Crown Ethers and lonophores -- 13-12. Preparation and Reactions of Sulfides -- 13-13. Spectroscopy of Alcohols, Phenols, and Ethers -- Something Extra Ethanol: Chemical, Drug, Poison -- A. Preview of Carbonyl Chemistry -- I. Kinds of Carbonyl Compounds -- II. Nature of the Carbonyl Group -- III. General Reactions of Carbonyl Compounds -- IV. Summary -- 14. Aldehydes and Ketones: Nucleophilic Addition Reactions -- 14-1. Naming Aldehydes and Ketones -- 14-2. Preparing Aldehydes and Ketones -- 14-3. Oxidation of Aldehydes -- 14-4. Nucleophilic Addition Reactions of Aldehydes and Ketones -- 14-5. Nucleophilic Addition of H20: Hydration -- 14-6. Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation -- 14-7. Nucleophilic Addition of Amines: Imine and Enamine Formation -- 14-8. Nucleophilic Addition of Alcohols: Acetal Formation -- 14-9. Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction -- 14-10. Biological Reductions -- 14-11. Conjugate Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones -- 14-12. Spectroscopy of Aldehydes and Ketones -- Something Extra Enantioselective Synthesis -- 15. Carboxylic Acids and Nitriles -- 15-1. Naming Carboxylic Acids and Nitriles -- 15-2. Structure and Properties of Carboxylic Acids --

Contents note continued: 15-3. Biological Acids and the Henderson-Hasselbalch Equation -- 15-4. Substituent Effects on Acidity -- 15-5. Preparing Carboxylic Acids -- 15-6. Reactions of Carboxylic Acids: An Overview -- 15-7. Chemistry of Nitriles -- 15-8. Spectroscopy of Carboxylic Acids and Nitriles -- Something Extra Vitamin C -- 16. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions -- 16-1. Naming Carboxylic Acid Derivatives -- 16-2. Nucleophilic Acyl Substitution Reactions -- 16-3. Reactions of Carboxylic Acids -- 16-4. Reactions of Acid Halides -- 16-5. Reactions of Acid Anhydrides -- 16-6. Reactions of Esters -- 16-7. Reactions of Amides -- 16-8. Reactions ofThioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives -- 16-9. Polyamides and Polyesters: Step-Growth Polymers -- 16-10. Spectroscopy of Carboxylic Acid Derivatives -- Something Extra Lactam Antibiotics -- 17. Carbonyl Alpha-Substitution and Condensation Reactions -- 17-1. Keto-Enol Tautomerism -- 17-2. Reactivity of Enols: a-Substitution Reactions -- 17-3. Alpha Bromination of Carboxylic Acids -- 17-4. Acidity of a Hydrogen Atoms: Enolate Ion Formation -- 17-5. Alkylation of Enolate Ions -- 17-6. Carbonyl Condensations: The Aldol Reaction -- 17-7. Dehydration of Aldol Products -- 17-8. Intramolecular Aldol Reactions -- 17-9. Claisen Condensation Reaction -- 17-10. Intramolecular Claisen Condensations: The Dieckmann Cyclization -- 17-11. Conjugate Carbonyl Additions: The Michael Reaction -- 17-12. Carbonyl Condensations with Enamines: The Stork Reaction -- 17-13. Biological Carbonyl Condensation Reactions -- Something Extra Barbiturates -- 18. Amines and Heterocycles -- 18-1. Naming Amines -- 18-2. Properties of Amines -- 18-3. Basicity of Amines -- 18-4. Basicity of Arylamines -- 18-5. Biological Amines and the Henderson-Hasselbalch Equation -- 18-6. Synthesis of Amines -- 18-7. Reactions of Amines -- 18-8. Heterocyclic Amines -- 18-9. Fused-Ring Heterocycles -- 18-10. Spectroscopy of Amines -- Something Extra Green Chemistry -- 19. Biomolecules: Amino Acids. Peptides, and Proteins -- 19-1. Structures of Amino Acids -- 19-2. Amino Acids and the Henderson-Hasselbalch Equation: Isoelectric Points -- 19-3. Synthesis of Amino Acids -- 19-4. Peptides and Proteins -- 19-5. Amino Acid Analysis of Peptides -- 19-6. Peptide Sequencing: The Edman Degradation -- 19-7. Peptide Synthesis -- 19-8. Protein Structure -- 19-9. Enzymes and Coenzymes -- 19-10. How Do Enzymes Work? Citrate Synthase -- Something Extra The Protein Data Bank -- 20. Amino Acid Metabolism -- 20-1. Overview of Metabolism and Biochemical Energy -- 20-2. Catabolism of Amino Acids: Deamination -- 20-3. Urea Cycle -- 20-4. Catabolism of Amino Acids: The Carbon Chains -- 20-5. Biosynthesis of Amino Acids -- Something Extra Visualizing Enzyme Structures -- 21. Biomolecules: Carbohydrates -- 21-1. Classifying Carbohydrates -- 21-2. Representing Carbohydrate Stereochemistry: Fischer Projections -- 21-3. D, L Sugars -- 21-4. Configurations of the Aldoses -- 21-5. Cyclic Structures of Monosaccharides: Anomers -- 21-6. Reactions of Monosaccharides -- 21-7. Eight Essential Monosaccharides -- 21-8. Disaccharides -- 21-9. Polysaccharides and Their Synthesis -- 21-10. Some Other Important Carbohydrates -- Something Extra Sweetness -- 22. Carbohydrate Metabolism -- 22-1. Hydrolysis of Complex Carbohydrates -- 22-2. Catabolism of Glucose: Glycolysis -- 22-3. Conversion of Pyruvate to Acetyl CoA -- 22-4. Citric Acid Cycle -- 22-5. Biosynthesis of Glucose: Gluconeogenesis -- Something Extra Influenza Pandemics -- 23. Biomolecules: Lipids and Their Metabolism -- 23-1. Waxes, Fats, and Oils -- 23-2. Soap -- 23-3. Phospholipids -- 23-4. Catabolism of Triacylglycerols: The Fate of Glycerol -- 23-5. Catabolism of Triacylglycerols: β-Oxidation -- 23-6. Biosynthesis of Fatty Acids -- 23-7. Prostaglandins and Other Eicosanoids -- 23-8. Terpenoids -- 23-9. Steroids -- 23-10. Biosynthesis of Steroids -- 23-11. Some Final Comments on Metabolism -- Something Extra Statin Drugs -- 24. Biomolecules: Nucleic Acids and Their Metabolism j -- 24-1. Nucleotides and Nucleic Acids -- 24-2. Base Pairing in DNA: The Watson-Crick Model -- 24-3. Replication of DNA -- 24-4. Transcription of DNA -- 24-5. Translation of RNA: Protein Biosynthesis -- 24-6. DNA Sequencing -- 24-7. DNA Synthesis -- 24-8. Polymerase Chain Reaction -- 24-9. Catabolism of Nucleotides -- 24-10. Biosynthesis of Nucleotides -- Something Extra DNA Fingerprinting -- e25. Secondary Metabolites: An Introduction to Natural Products Chemistry -- 25-1. Classifying Natural Products -- 25-2. Biosynthesis of Pyridoxal Phosphate -- 25-3. Biosynthesis of Morphine -- 25-4. Biosynthesis of Erythromycin -- Something Extra Bioprospecting: Hunting for Natural Products -- e26. Orbitals and Organic Chemistry: Pericyclic Reactions -- 26-1. Molecular Orbitals of Conjugated Pi Systems -- 26-2. Electrocyclic Reactions -- 26-3. Stereochemistry of Thermal Electrocyclic Reactions -- 26-4. Photochemical Electrocyclic Reactions -- 26-5. Cycloaddition Reactions -- 26-6. Stereochemistry of Cycloadditions -- 26-7. Sigmatropic Rearrangements -- 26-8. Some Examples of Sigmatropic Rearrangements -- 26-9. Summary of Rules for Pericyclic Reactions -- Something Extra Vitamin P. the Sunshine Vitamin -- e27. Synthetic Polymers -- 27-1. Chain-Growth Polymers -- 27-2. Stereochemistry of Polymerization: Ziegler-Natta Catalysts -- 27-3. Copolymers -- 27-4. Step-Growth Polymers -- 27-5. Olefin Metathesis Polymerization -- 27-6. Polymer Structure and Physical Properties -- Biodegradable Polymers -- Appendices -- A. Nomenclature of Polyfunctional Organic Compounds -- B. Acidity Constants for Some Organic Compounds -- C. Glossary -- D. Answers to In-Text Problems.