CH 223 : Structure and Stereochemistry


Frontier molecular orbitals and organic reactions: Introduction to HOMO and LUMO, classification of nucleophiles and electrophiles based on frontier orbitals, importance of antibonding orbitals; a brief introduction to pericyclic reactions, orbital symmetry considerations in Diels-Alder and electrocyclic reactions. [6 hrs]

Stereochemistry: Concept of chirality, center and axis of chirality, examples of compounds with one and two chiral centers, enatiomers and diastereomers, prochiral faces, enantio and diastereotopicity, absolute and relative configuration, configuration descriptors R/S and E/Z notations, optical purity, enantio/diastereomeric excess. [12 hrs]

Introduction to spectroscopic techniques: Ultraviolet and visible spectroscopy: electronic transitions, Beers law, interpretation of UV-VIS spectra, Woodward-Fieser rules.

Infrared Spectroscopy: molecular vibrations and Hooke’s law, IR active and IR inactive vibrations, characteristic IR absorptions of important functional groups.

Mass spectrometry: different methods of ionization (EI, CI, electrospray, laser desorption),
molecular ion and fragment peaks, common fragmentation pathways

Nuclear Magnetic Resonance (NMR) spectroscopy: brief introduction to theory behind NMR, magnetic shielding by electrons, measurement of 1H and 13C chemical shifts, characteristic values of chemical shifts for various functional groups,theory of spin-spin coupling, C13 spectra and proton-decoupling
Basic applications of these spectroscopic methods to problem solving. [12 hrs]

Reactions of aromatic compounds: Energy profile diagrams of electrophilic aromatic substitution reactions; Nucleophilic aromatic substitutions: addition-elimination mechanism, elimination-addition mechanism (benzynes) [5 hrs]

Text References

1) K. P. C. Volhardt and N. E. Schore “Organic Chemistry: Structure and Function”, 5th Ed., W. H. Freeman and Company, 2007.
2) L. G. Wade Jr. “Organic Chemistry”. 7th Ed., Prentice Hall, 2009
3) T. W. G. Solomons, C.G. Fryhle. “Organic Chemistry”, 9th Ed., Wiley-India, 2008.
4) J. Clayden, N. Greeves, S. Warren and P. Wothers, “Organic Chemistry”, 1st Ed., Oxford University Press, 2001.
5) F. A. Carey and R. J. Sundburg, “Advanced Organic Chemistry, Part A&B”, 5th Ed., Plenum Press, 2007.