Organic Chemistry, 9th edition

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 Rotation About Single Bonds

PART 2: ELECTROPHILIC ADDITION REACTIONS, STEREOCHEMISTRY, AND ELECTRON DELOCALIZATION

• TUTORIAL: Using Molecular Models to Understand Structure
• 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
• TUTORIAL: Kinetics
• 6. The Reactions of Alkenes • The Stereochemistry of Addition Reactions
• TUTORIAL: An Overview of Functional Groups and How They React
• 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 • Electronic Effects
• TUTORIAL: Drawing Resonance Contributors

PART 3: SUBSTITUTION AND ELIMINATION REACTIONS

• 9. Substitution and Elimination Reactions
• 10. Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds • An Introduction to Organometallic Compounds
• 11. Radicals
• TUTORIAL: Drawing Curved Arrows in Radical Systems
• TUTORIAL: Synthesizing Organic Compounds I

PART 4: IDENTIFICATION OF ORGANIC COMPOUNDS

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

PART 5: CARBONYL COMPOUNDS

• 14. Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
• 15. Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
• TUTORIAL: Predicting Mechanisms
• 16. Reactions at the alpha-Carbon
• TUTORIAL: Synthesizing Organic Compounds II

PART 6: AROMATIC COMPOUNDS

• 17. Reactions of Benzene and Substituted Benzenes
• 18. More About Amines • Reactions of Heterocyclic Aromatic Compounds
• 19. Coupling Reactions and Metathesis

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

MATH AND CHEMISTRY-BASED GLOSSARY

USEFUL REFERENCES

• Organizing What We Know About the Reactions of Organic Chemistry
• Periodic Table of the Elements
• Common Functional Groups
• Approximate pKa Values
• Common Symbols and Abbreviations