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Review of Atomic and Molecular Structure Introduction Atomic and Molecular Structure Bonding Review Problems Alkanes and Friends: Structure, Bonding, Properties, and Nomenclature Introduction Hybridization in Methane, Ammonia, and Water Drawing Molecules Introduction to Alkanes Stability, Strain, and Properties of Alkanes and Cycloalkanes Review Problems Alkenes, Alkynes, and Aromatic Compounds Alkenes Aromatic Hydrocarbons Alkynes: Hydrocarbons Containing Triple Bonds Resonance Review Problems Heteroatom-Containing Functional Groups Compounds Containing sp3 Nitrogen Atoms Molecules Containing sp2 Nitrogen Atoms Molecules with sp-Hybridized Nitrogen Compounds Containing sp3 Oxygen Compounds Containing sp2 Oxygen Priorities in Nomenclature Structure and Bonding in Some Highly Reactive Species More Resonance Review Problems More Challenging Problems Purification and Identification of Organic Compounds 1 Introduction Purification of Organic Compounds Mass Spectrometry UV/Visible Spectroscopy Infrared Spectroscopy Review Problems More Challenging Problems Identification of Organic Compounds 2: Nuclear Magnetic Resonance Spectroscopy Introduction Chemical Shifts Spin-Spin Coupling Protons Attached to Oxygen and Nitrogen 13C NMR Spectroscopy Review Problems More Challenging Problems Stereochemistry Introduction Conformations of Alkanes Cycloalkanes Chirality Fischer Projections Review Problems More Challenging Problems Introduction to Mechanism Introduction Studying Organic Reaction Mechanisms Classification of Reactions Acids and Bases Tautomers: A Slight Digression Writing Mechanisms Using Curly Arrows Review Problems More Challenging Problems Nucleophilic Substitution at Saturated Carbon Introduction Mechanistic Types Stereochemical Implications Effect of Nucleophile Effect of the Leaving Group Effect of Substrate Structure Effect of Solvents Competing Reactions Competition between SN1 and SN2 Processes Applications and Scope of the Reaction Neighboring Group Participation and Intramolecular Reactions Review Problems More Challenging Problems Elimination Reactions Introduction Mechanisms Stereochemistry Regiochemistry Effect of Substrate Substitution versus Elimination Carbocation Rearrangements Examples and Applications Elimination to Give Alkynes Other Elimination Reactions Review Problems More Challenging Problems Addition Reactions Introduction Electrophilic Reactions Radical Addition Reactions Multicenter Processes Hydrogenation Review Problems More Challenging Problems Electrophilic Aromatic Substitution Introduction Electrophiles Orientation Effects Reactions of Polycyclic Aromatic Compounds Heterocyclic Aromatic Compounds Review Problems More Challenging Problems Nucleophilic Aromatic Substitution and Synthesis of Aromatic Compounds Introduction Unimolecular Nucleophilic Substitution of Aromatic Compounds: The Reactions of Diazonium Salts with Simple Nucleophiles Azo Coupling Reactions Nucleophilic Substitution of Aryl Halides, SN2Ar Substitution of Haloheterocycles Substitution via Benzyne and Related Intermediates Reactions in Side Chains of Aromatic Compounds Reduction of Benzene Rings Carbon-Aryl Bond Formation Aromatic Synthesis Review Problems More Challenging Problems Addition to Carbon-Heteroatom Double Bonds Introduction and Review Mechanism of Addition Reactions Reversible Addition Reactions Irreversible Addition Reactions Review Problems More Challenging Problems Substitution of Carbonyl Compounds: Carboxylic Acids and Their Derivatives Introduction: Review of Nomenclature Substitution Reaction Oxygen Nucleophiles Nitrogen Nucleophiles Synthesis of Acid Chlorides Hydride as Nucleophile Carbon Nucleophiles Review Problems More Challenging Problems Lipids and Carbohydrates Introduction Lipids Carbohydrates Review Problems More Challenging Problems Substitution alpha and ss to Carbonyl Groups Introduction Formation of Enols and Enolates Isomerizations Involving Enols and Enolates Reactions of Enols and Enolates with Electrophiles Two Useful Reactions of Nonenolizable Carbonyl Compounds Reactions at the ss-Position of alpha,ss-Unsaturated Carbonyl Compounds and Other Electron-Poor Alkenes Review Problems More Challenging Problems Rearrangement Reactions Introduction Migration to Electron-Deficient Carbon Migration to Electron-Deficient Nitrogen Migration to Electron-Deficient Oxygen: The Baeyer-Villiger Oxidation Anionic Rearrangements Neutral Rearrangements Review Problems More Challenging Problems Synthesis 1: One-Group Disconnections Introduction Simple Disconnections and the Retrosynthetic Approach One-Group Disconnections Review Problems More Challenging Problems Synthesis 2: Two-Group Disconnections and Protecting Groups Introduction to Two-Group Disconnections 1,2-Difunctionalized Compounds 1,3-Difunctionalized Compounds 1,4-Difunctionalized Compounds 1,5-Difunctionalized Compounds Robinson Annulation 1,6-Difunctionalized Compounds Pericyclic Disconnections Protecting Group Further Reading Review Problems More Challenging Problems More Challenging Problems Polymeric Materials Introduction Polymer Structures Preparation of Addition or Chain-Growth Polymers Preparation of Step-Reaction Polymers Unusual Biopolymers Review Problems More Challenging Problems Amines, Alkaloids, Amino Acids, Peptides, and Nucleic Acids Synthesis of Amines Alkaloids Amino Acids Peptides Nucleic Acids Review Problems More Challenging Problems Catalysis of Organic Reactions Introduction Catalysis by Acids and Bases Lewis Acid Catalysis Phase-Transfer Catalysis Reactions Catalyzed by Metal Surfaces Reactions Catalyzed by Transition Metal Complexes Organocatalysis Enzyme Catalysis Review Problems More Challenging Problems Organic Chemistry in Industry Introduction Process Chemistry versus Research Chemistry Pharmaceutical Industry Agrochemicals Dyes and Colorants Review Problems Further Reading Organic Chemistry and the Environment Introduction Pesticides Endocrine Disruptors Chlorofluorocarbons and Their Replacements Polycyclic Aromatic Hydrocarbons Plastics: Recycle, Degrade, or Burn? Is "Green Chemistry" the Future? Review Problems Further Reading Organic Chemistry in Forensic Science Introduction Drugs of Abuse Poisons and Poisoning Testing for Blood Dyes, Inks, and Paper Trace Evidence Visualization of Fingerprints Review Problems Appendix A: Glossary of Abbreviations and Acronyms Appendix B: Some Common/Trivial Names You Need to Know |