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Indian Institute of Science Education and Research Bhopal

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 (A^1,2 and A^1,3) 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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