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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