Chemistry
CHM 411: Physical Organic Chemistry (4)
Prerequisites: CHM 311, CHM 312
Learning Objectives:
This course gives an in-depth understanding of a broad range of organic reactions from physical organic chemistry perspective. The topics include thermodynamic & kinetic control of organic reactions, Curtin-Hammett Principle, probing the reaction mechanisms by kinetic isotope effects, stereoelectronic effects in conformations, allylic strain and various selected reactions. Also, a detailed study and application of the theories/rules governing various pericyclic reactions will be carried.
Course Contents:
Chemical Equilibria and Chemical Reactivity:
- Thermodynamic and kinetic control of reactions
- Correlation of reactivity with structure, linear free energy relationships, Hammond’s postulate, Curtin-Hammett principle, substituent constants and reaction constants
- Various types of catalysis and isotope effects, importance in the elucidation of organic reaction mechanisms
- Role of stereoelectronic effects in the reactivity of acetals, esters, amides and related functional groups
- Reactions at sp3, sp2, and sp carbons, Cram, Felkin-Ahn, Zimmerman-Traxler, Houk, Cieplak, exterior frontier orbital extension (EFOE) and cation-complexation models as applied to p-facial stereoselectivity
- Allylic strain (A1,2 and A1,3) and other strains
Pericyclic Reactions:
- Conservation of orbital symmetry, Woodward-Hoffmann rules, frontier molecular orbital (FMO) theory
- Orbital overlap effects in cycloadditions, electrocyclizations, sigmatropic rearrangements and chelotropic reactions
- Paterno-Buchi, Norrish type I and II reactions
Suggested Readings :
- Isaacs, N. S. Physical Organic Chemistry, Prentice Hall, 1996.
- Deslongchamps, P. Stereolectronic Effects in Organic Chemistry, Elsevier Science, 1983.
- Carey, F. A., Sundberg, R. J. Advanced Organic Chemistry, Part A and B, Springer, 2007.
- Turro, N. J. Modern Molecular Photochemistry, University Science Books, 1991.
- Anslyn, E. V., Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, 2005.
- Woodward, R. B., Hoffmann, R. The Conservation of Orbital Symmetry, Verlag Chemie, 1970.
- Lehr, R. E., Marchand, A. P. Orbital Symmetry: A Problem Solving Approach, Academic Press, 1972.
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