Stereochemistry

Course Code2873Marks: 100Credits: 4Class Hours: 60Course TitleStereochemistry 1. Fundamentals of Stereochemistry: Stereochemistry and stereoisomerism. 2.Isomerism: Cis-trans isomerism, interconversion of cis-trans isomers; Determination of configuration of geometrical isomers by chemical and physical methods, conformation of acyclic and cyclic molecules. Physical and spectral properties of diastereoisomers and conformers, conformation and reactivity. 3.Configuration: D & L, threo erythro, R & S configurations. Absolute and relative configurations and their correlation. Relative and absolute configurations, determination of R-S configuration and their Chemical interconversion; Chiral, Prochiral and pseudochiral molecules. Chirality in molecules devoid of chiral centre; atropisomerism, biphenyl, allenes and spiranes; Conformational analysis of biopolymers; conformation of glycosides, starch, cellulose and their physical properties; Conformation of proteins, nucleic acids; 4.Optical Activity and Optical Isomerism:Cause of optical activity. Chirality (Dissymmetry and asymmetry), prochirality, pseudo chirality. Symmetry elements. Optical isomers, diasterecoisomers, enantiomers, epimeners, anomers, meso and racemic compounds. Racemic modification and their resolution. Atropisomerism: biphenyls, allenes and spiranes. 5.Geometrical Isomerism:Conditions, Configurations of geometrical isomers: cis-trans. E/Zsystem, Syn-anti. Physical properties and configurational ssignment of geometrical isomers. Geometrical isomerism of polyenes, carbon-nitrogen, nitrogen-nitiogen double bonds and cyclic compounds (cis-trans isomerism in disubstituted cyclohexanes). 6.Stereochemistry of Fused Ring:Stereochemistry of decalines, perhydroanthrancene, perhydrophenanthrene, their optical activity and relative stability. Fused rings and bridgedring systems. Bredt’s rule and its exceptions in flexible ring systems. 7.Conformation:Conformation and conformers. Conformation of propane, butane, ethanediol, dihydroxystyrene, dichlorostyrene, their physical properties and stability. Stability of threo and crythro, meso and d1 compounds, Conformation of cyclobutane, cyclopentane and cyclohexane and their stability. Conformation of mono and disubstituted cyclohexanes (1,3 –diaxial interactions, butaneguache interactions etc)8.Optical Rotation and Rotatory Power:Factors leading to chirality. Molecular dissymmetry. Atomic dissymmetry and conformational asymmetry, Circular bifringence and circular dichroism (CD). Cotton effect, Dependance of optical rotation on wavelength –optical rotatory dispersion (ORD) Books Recommended:1.I.L. Eliel, Stereochemistry of Carbon Compounds, Tata Mc Graw-Hill, 19792.R.T. Morrison and R.N. Boyd, Organic Chemistry, Fifth edition, Prentice-Hall of India, New Delhi, 1989.3.Handrickson and Pyne, Organic Chemistry, McGraw-Hill. 4.I.L. Finar, Organic Chemistry Vol. II, ELBS, Fifty edication, 1985