Details of CH3104 (Autumn 2019)

Level: 3 Type: Theory Credits: 4.0

Course CodeCourse NameInstructor(s)
CH3104 Stereochemistry and asymmetric synthesis Suman De Sarkar,
Sureshkumar Devarajulu

Stereochemistry of Acyclic Compounds (10 Lectures)
Representation of molecules in Fischer, saw horse, flying-wedge and Newman formulae and their inter translations, symmetry elements, molecular chirality.
Configuration: stereogenic units
i) Stereocentres: stereogenicity, chirotopicity, systems involving 1,2,3 centres
D/L and R/S descriptor, threo/erythro and syn/anti nomenclatures
ii) Stereoaxis: chiral axis in allenes and biphenyls, R/S descriptor; cis/trans, syn/anti, E/Z descriptors (for C=C, C=N).

Optical Activity, Topicity and Conformation (10 Lectures)
Specific rotation, optical purity (enantiomeric excess)
Topicity of ligands and faces (elementary idea): Pro-R, Pro-S and Re/Si descriptors. Conformation: Conformational nomenclature, eclipsed, staggered, gauche and anti; dihedral angle, torsion angle, energy barrier of rotation, relative stability of conformers on the basis of steric effect, dipole-dipole interaction, H-bonding etc.

Stereochemistry of Cyclic Compounds (10 Lectures)
Conformational analysis: monocyclic compounds, fused and bridged ring compounds
Dynamic stereochemistry: conformation and reactivity
Elimination (E2), rearrangement, nucleophilic substitution (SN1, SN2, NGP)

Asymmetric Synthesis (10 Lectures)
Introduction to asymmetric synthesis
Basic principles and examples of stereospecific, stereoselective, enantioselective and diastereoselective reactions

1. Stereochemistry of Organic Compounds: Principles and Applications by D. Nasipuri.
2. Stereochemistry of Carbon Compounds by E. L. Eliel and S. H. Wilen.
3. Advanced Organic Chemistry: Reaction Mechanism by R. Bruckner.
4. Organic Chemistry by J. Clayden, N. Greeves and S. Warren.

Course Credit Options

Sl. No.ProgrammeSemester NoCourse Choice
1 IP 1 Core
2 IP 3 Not Allowed
3 IP 5 Not Allowed
4 MR 1 Not Allowed
5 MR 3 Not Allowed
6 MS 5 Core
7 RS 1 Not Allowed
8 RS 2 Not Allowed