1. Covalent Bonding and Shapes of Molecules.

Things You Should Know I: General Conclusions from Quantum Mechanics.

2. Alkanes and Cycloalkanes.

3. Stereochemistry and Chirality.

4. Acids and Bases.

5. Alkenes.

Things You Should Know II: Nucleophiles and Electrophiles.

Things You Should Know III: Reaction Mechanisms.

6. Reactions of Alkenes.

7. Alkynes.

8. Haloalkanes, Halogenation, and Radical Reactions.

Things You Should Know IV: Common Mistakes in Arrow Pushing.

9. Nucleophilic Substitution and β -Elimination.

10. Alcohols.

11. Ethers, Epoxides, and Sulfides.

12. Infrared Spectroscopy.

13. Nuclear Magnetic Resonance Spectroscopy.

14. Mass Spectrometry.

15. Introduction to Organometallic Compounds.

16. Aldehydes and Ketones.

17. Carboxylic Acids.

Things You Should Know V: Carboxylic Acid Derivative Reaction Mechanisms.

18. Functional Derivatives of Carboxylic Acids.

19. Enolate Anions and Enamines.

20. Dienes, Conjugated Systems, and Pericyclic Reactions.

21. Benzene and the Concept of Aromaticity.

22. Reactions of Benzene and Its Derivatives.

23. Amines.

24. Catalytic Carbon–Carbon Bond Formation.

25. Carbohydrates.

26: Lipids.

27. Amino Acids and Proteins.

28. Nucleic Acids.

29. Organic Polymer Chemistry.

Appendices:

1. Thermodynamics and the Equilibrium Constant.

2. Major Classes of Organic Acids.

3. Bond Dissociation Enthalpies.

4. Characteristic 1H-NMR Chemical Shifts.

5. Characteristic 13C Chemical Shifts.

6. Characteristic Infrared Absorption Frequencies.

7. Electrostatic Potential Maps.

8. Summary of Stereochemical Terms.

9. Summary of the Rules of Nomenclature.

10. Organic Chemistry Reaction Roadmaps.