PART 1: 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 2: 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 3: 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 4: IDENTIFICATION OF ORGANIC COMPOUNDS

• 13. Mass Spectrometry; Infrared Spectroscopy; and UV/Vis Spectroscopy
• 14. NMR Spectroscopy

PART 5: 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 6: AROMATIC COMPOUNDS

• 18. Reactions of Benzene And Substituted Benzenes
• 19. More About Amines • Reactions of Heterocyclic Compounds

PART 7: 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 8: SPECIAL TOPICS IN ORGANIC CHEMISTRY

• 27. Synthetic Polymers
• 28. Pericyclic Reactions

Appendices

• I. pK_a Values
• II. Kinetics
• III. Summary of Methods Used to Synthesize a Particular Functional Group
• IV. Summary of Methods Employed to Form Carbon-Carbon Bonds
• V. Spectroscopy Tables
• VI. Physical Properties of Organic Compounds
• VII. Answers to Selected Problems