Professor James Nowick |
CHEM 125: Advanced Organic Chemistry The course builds upon the concepts and skills learned in a typical yearlong sophomore-level organic chemistry class. Topics include: The Chemical Literature and Databases; Stereochemistry and Structural Organic Chemistry; Synthetic Organic Chemistry; Mechanistic and Physical Organic Chemistry; NMR Spectroscopy. |
Lecture 2. Chapter 1. Nomenclature: Spirocyclic Compounds, Polycyclic Hydrocarbons, and Heterocyclic Compounds
Lecture 3. Chapter 2. Databases and the Chemical Literature
Lecture 4. Chapter 3. Stereochemistry: Properties of Stereoisomers
Lecture 5. Chapter 3. Concepts in Stereochemistry
Lecture 6. Chapter 3. Stereoselectivity in the Aldol Reaction
Lecture 8. Chapter 4. Reaction Kinetics
Lecture 9. Chapter 4. Effect of Activation Energies and Temperature on Reaction Rates: The Eyring Equation
Lecture 10. Chapter 4. Linear Free-Energy Relationships. The Kinetic Isotope Effect
Lecture 11. Chapter 5. Molecular Orbitals and Aromaticity
Lecture 12. Chapter 5. Introduction to Pericyclic Reactions. Electrocyclic Reactions
Lecture 13. Chapter 5. Pericyclic Reactions: Cycloadditions and Sigmatropic Rearrangments
Lecture 14. Chapter 6. Functional Group Transformations, Part 1. The Importance of Oxidation State
Lecture 15. Chapter 6. Functional Group Transformations, Part 2. Oxidation and Reduction of Alcohols and Carbonyl Compounds
Lecture 16. Chapter 6. Functional Group Transformations, Part 3. Some Stereochemically and Mechanistically Interesting Reactions: Stereoselective Reduction; Mitsunobu Reaction; Barton-McCombie Deoxygenation
Lecture 17. Chapter 7. Carbon-Carbon Bond Forming Reactions, Part 1. The Importance of the Carbonyl Group
Lecture 18. Chapter 7. Carbon-Carbon Bond Forming Reactions, Part 2. Claisen Condensation and Michael Addition
Lecture 19. Chapter 7. Carbon-Carbon Bond Forming Reactions, Part 3. Acid-Catalyzed Aldol Reactions and the Mannich Reaction
Lecture 20. Chapter 7. Carbon-Carbon Bond Forming Reactions, Part 4. Enamines, the Wittig Reaction, and Cyclopropanation
Lecture 21. Chapter 8. Concepts in Multistep Synthesis. Umpolung: Benzoin Condensation, Acyl Anion Equivalents, and the Acyloin Condensation
Lecture 22. Chapter 8. Concepts in Multistep Synthesis. Retrosynthetic Analysis. The Diels-Alder Reaction and the Robinson Annulation
Lecture 23. Chapter 9. Physical Influences on Reactions. Effects of Concentration, Stoichiometry, and Other Reaction Conditions
Lecture 24. Chapter 9. Physical Influences on Reactions, continued. Effects of Temperature, Phase-Transfer Catalysis, Ring Size, Solid-Supported Reactions and Reagents
Lecture 25. Chapter 10. Organic Spectroscopy. NMR Spectroscopy: How NMR Works. Chemical Shifts
Lecture 27. Chapter 10. Organic Spectroscopy. 1H NMR Coupling Constants in Determining Sterochemistry and Regiochemistry
Lecture 28. Chapter 10. Organic Spectroscopy. 13C NMR Spectroscopy. Introduction to 2D NMR. COSY and HMQC