Lectures (Video)
- 1. How Do You Know?
- 2. Force Laws, Lewis Structures and Resonance
- 3. Double Minima, Earnshaw's Theorem and Plum-Puddings
- 4. Coping with Smallness and Scanning Probe Microscopy
- 5. X-Ray Diffraction
- 6. Seeing Bonds by Electron Difference Density
- 7. Quantum Mechanical Kinetic Energy
- 8. One-Dimensional Wave Functions
- 9. Chladni Figures and One-Electron Atoms
- 10. Reality and the Orbital Approximation
- 11. Orbital Correction and Plum-Pudding Molecules
- 12. Overlap and Atom-Pair Bonds
- 13. Overlap and Energy-Match
- 14. Checking Hybridization Theory with XH3
- 15. Chemical Reactivity: SOMO, HOMO, and LUMO
- 16. Recognizing Functional Groups
- 17. Reaction Analogies and Carbonyl Reactivity
- 18. Amide, Carboxylic Acid and Alkyl Lithium
- 19. Oxygen and the Chemical Revolution (Beginning to 1789)
- 20. Rise of the Atomic Theory (1790-1805)
- 21. Berzelius to Liebig and Wöhler (1805-1832)
- 22. Radical and Type Theories (1832-1850)
- 23. Valence Theory and Constitutional Structure (1858)
- 24. Determining Chemical Structure by Isomer Counting (1869)
- 25. Models in 3D Space (1869-1877); Optical Isomers
- 26. Van't Hoff's Tetrahedral Carbon and Chirality
- 27. Communicating Molecular Structure in Diagrams and Words
- 28. Stereochemical Nomenclature; Racemization and Resolution
- 29. Preparing Single Enantiomers and the Mechanism of Optical Rotation
- 30. Esomeprazole as an Example of Drug Testing and Usage
- 31. Preparing Single Enantiomers and Conformational Energy
- 32. Stereotopicity and Baeyer Strain Theory
- 33. Conformational Energy and Molecular Mechanics
- 34. Sharpless Oxidation Catalysts and the Conformation of Cycloalkanes
- 35. Understanding Molecular Structure and Energy through Standard Bonds
- 36. Bond Energies, the Boltzmann Factor and Entropy
- 37. Potential Energy Surfaces, Transition State Theory
Introductory Organic Chemistry - Lecture 17
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Lecture 17 - Reaction Analogies and Carbonyl Reactivity
Continuing the examination of molecular orbital theory as a predictor of chemical reactivity, this lecture focuses on the close analogy among seemingly disparate organic chemistry reactions: acid-base, SN2 substitution, and E2 elimination. All these reactions involve breaking existing bonds where LUMOs have antibonding nodes while new bonds are being formed. The three-stage oxidation of ammonia by elemental chlorine is analyzed in the same terms. The analysis is extended to the reactivity of the carbonyl group and predicts the trajectory for attack by a high HOMO. This predicted trajectory was validated experimentally by Bürgi and Dunitz, who compared numerous crystal structures determined by X-ray diffraction.
Prof. J. Michael McBride
CHEM 125: Freshman Organic Chemistry, Fall 2008 (Yale University: Open Yale) http://oyc.yale.edu Date accessed: 2009-11-11 License: Creative Commons BY-NC-SA |
Lecture Material
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