CH 839 : Physical Organic and Stereochemistry

Autumn elective .CH 805 : Stereochemistry and Reactivity of Organic Compounds has been renamed as  CH 839 : Physical Organic and Stereochemistry

Syllabus

Structure and bonding. Orbital symmetry and orbital mixing rules.  Steric and electronic effects. Structure and properties of charged and neutral reactive intermediates. Structure and energetics. Inter- and intramolecular non-covalent interactions. Reactivity, kinetics and mechanisms, energy surfaces and transition states: Hammond Postulate, Curtin-Hammett principle. Linear free energy relationship: Hammett and Taft equations. Isotope effects. Acids and bases. Aromaticity. General principles of organo, metal (including photoredox) and enzyme catalysis. Study of organic reaction mechanisms: electrophilic, nucleophilic, radical and pericyclic reactions.

Structure and stereochemistry. Chirality. Symmetry elements and point groups. Relative and absolute configuration. Chiral molecules without chiral centers. Conformation of open chain and cyclic compounds, atropisomerism. Properties and separation of stereoisomers. Topicity of ligands and faces. Stereochemistry of ring systems: fused, bridged and caged. Different types of strain, modes of ring formation, Baldwin rule. Stereoselective and stereospecific synthesis. Stereochemistry and mechanism of reactions.

Text References

1. E. V. Anslyn and D. A. Dougherty, Modern Physical Organic Chemistry, University Science, 2005.

2. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, Springer, 2006.

3. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, John Wiley and Sons, Singapore, 2003.

4. C. Wolf, Dynamic Stereochemistry of Chiral Compounds: Principles and Applications, Royal Society of Chemistry, Cambridge, UK, 2008.

5. D. Nasipuri, Stereochemistry of Organic Compounds: Principles and Applications, 2nd Ed, New Age International, New Delhi, 2007.

6. P. Vogel and K.N. Houk, Organic Chemistry-Theory, Reactivity and Mechanism in Modern Synthesis, Wiley-VCH, 2019.