PART ONE: An Introduction to the Study of Organic Chemistry 1. Remembering General Chemistry: Electronic Structure and Bonding 2. Acids and Bases: Central to Understanding Organic Chemistry TUTORIAL: Acids and Bases 3. An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure PART TWO: Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization TUTORIAL: Using Molecular Models 4. Isomers: The Arrangement of Atoms in Space TUTORIAL: Interconverting Structural Representations 5. Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics TUTORIAL: Drawing Curved Arrows 6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions 7. The Reactions of Alkynes • An Introduction to Multistep Synthesis 8. Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction the Reactions of Benzene TUTORIAL: Drawing Resonance Contributors PART THREE: Substitution and Elimination Reactions 9. Substitution and Elimination Reactions of Alkyl Halides 10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds 11. Organometallic Compounds 12. Radicals TUTORIAL: Drawing Curved Arrows in Radical Systems PART FOUR: Identification of Organic Compounds 13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy 14. NMR Spectroscopy PART FIVE: Carbonyl Compounds 15. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives 16. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives 17. Reactions at the α-Carbon TUTORIAL: Synthesis and Retrosynthetic Analysis PART SIX: Aromatic Compounds 18. Reactions of Benzene And Substituted Benzenes 19. More About Amines • Reactions of Heterocyclic Compounds PART SEVEN: Bioorganic Compounds 20. The Organic Chemistry Of Carbohydrates 21. Amino Acids, Peptides, and Proteins 22. Catalysis in Organic Reactions and in Enzymatic Reactions 23. The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins 24. The Organic Chemistry of the Metabolic Pathways 25. The Organic Chemistry of Lipids 26. The Chemistry of the Nucleic Acids PART EIGHT: Special Topics in Organic Chemistry 27. Synthetic Polymers 28. Pericyclic Reactions Appendix I – pKa Values Appendix II – Kinetics Appendix III – Summary of Methods Used to Synthesize a Particular Functional Group Appendix IV – Summary of Methods Employed to Form Carbon-Carbon Bonds Appendix V – Spectroscopy Tables Appendix VI – Physical Properties of Organic Compounds Appendix VII – Answers to Selected Problems
