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 16
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Lecture 16 - Recognizing Functional Groups
This lecture continues the discussion of the HOMO/LUMO view of chemical reactivity by focusing on ways of recognizing whether a particular HOMO should be unusually high in energy (basic), or a particular LUMO should be unusually low (acidic). The approach is illustrated with BH3, which is both acidic and basic and thus dimerizes by forming unusual "Y" bonds. The low LUMOs that make both HF and CH3F acidic are analyzed and compared underlining the distinction between MO nodes that derive from atomic orbitals nodes (AON) and those that are antibonding (ABN). Reaction of HF as an acid with OH- is shown to involve simultaneous bond-making and bond-breaking.
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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Supplementary lecture material is listed below.1. Orbitals of HF an acid (substitution at H)
2. Orbitals of CH3F substitution at C (an acid)
3. Orbitals of O=CH2 the carbonyl group (an acid)
