This course would highlight the concepts and applications of molecular symmetry, isomerism, chirality, applications of stereochemistry in simple organic reactions etc. The students will be introduced to various symmetry elements and symmetry operations observed in various organic molecules, how to identify the symmetry elements and then determine the point groups etc. Then the students would learn the difference between conformation and configuration, various aspects of stereochemistry and will learn to visualize molecules in 3D. Then the course will deal with various organic reactions where stereochemistry plays a major role. This course is suitable for 1st and 2nd year B. Sc students studying Chemistry as one of the subjects in their curriculum. INTENDED AUDIENCE :1st and 2nd year B.Sc. studentsPREREQUISITES : Should have passed 10+2 with science INDUSTRIES SUPPORT :R&D section of Chemical, Pharmaceutical industry
Symmetry, Stereochemistry and Applications
Indian Institute of Science Education and Research, Mohali and NPTEL via Swayam
Overview
Syllabus
Week 1:Introduction, IUPAC nomenclature of organic compounds, Conformation and Configuration, Molecular symmetry elementsWeek 2:Molecular point groups, Conformational analysis of alkanes and substituted alkanes, Newman and Saw-horse projection Week 3:Conformation of cyclic molecules: cyclohexane, mono and disubstituted cyclohexane, cyclohexene, cis- and trans- decalene etcWeek 4:Isomerism: Stereoisomerism, topicity of ligands and faces, Enantiomers and Diastereomers, asymmetry and dissymmetry, Fisher Projection
Week 5:Stereoisomerism in chiral molecules- optical isomerism, Circular Dichroism (CD) and Optical Rotatory Dispersion (ORD) and their applications, racemization, D/L and R/S nomenclature, meso-compounds etc.Week 6:Pseudoasymmetry, Stereochemistry of Allenes, substituted Allenes, Atropeisomerism in Biphenyl and Spiro compounds, Geometrical isomerism (cis-/trans- and E/Z notations)Week 7:Diastereoisomerism in cyclic system- cyclopropane, cyclobutane, cyclohexane, compounds containing C=O, C=N, fused ring compoundsWeek 8:Application of stereochemistry in chemical reactions: Stereoselectivity, Stereospecificity, Regiospecific, Regioselective, Chemoselective reactions Introduction to rate of a reaction, rate determining step etc.
Week 9:Stereochemical aspects of basic organic reactions: SN1, SN2, SNi, NGP, E1 and E2 reaction mechanism, reactions of cyclohexane derivativesWeek 10:Cycloaddition reactions: Diels-Alder reactions, Hydroboration-Oxidation of alkenes,, Baeyer-Villiger Oxidation. Stereochemistry of Aldol condensation, Wittig reaction, Carbonyl addition reactionWeek 11:Stereochemistry of Molecular rearrangements: Pinacol rearrangement, Hoffman, Curtius, Schmidt and Lossen rearrangemnet, Beckmann, Wolff Rearrangement, Cope, Claisen rearrangementWeek 12:Introduction to crystallographic symmetry: 1D symmetry, Concept of 2D symmetry and lattices, notations of symmetry elements, space groups in 2D, 3D lattices, 32 point groups and their notations, crystal systems and Bravais lattices
Week 5:Stereoisomerism in chiral molecules- optical isomerism, Circular Dichroism (CD) and Optical Rotatory Dispersion (ORD) and their applications, racemization, D/L and R/S nomenclature, meso-compounds etc.Week 6:Pseudoasymmetry, Stereochemistry of Allenes, substituted Allenes, Atropeisomerism in Biphenyl and Spiro compounds, Geometrical isomerism (cis-/trans- and E/Z notations)Week 7:Diastereoisomerism in cyclic system- cyclopropane, cyclobutane, cyclohexane, compounds containing C=O, C=N, fused ring compoundsWeek 8:Application of stereochemistry in chemical reactions: Stereoselectivity, Stereospecificity, Regiospecific, Regioselective, Chemoselective reactions Introduction to rate of a reaction, rate determining step etc.
Week 9:Stereochemical aspects of basic organic reactions: SN1, SN2, SNi, NGP, E1 and E2 reaction mechanism, reactions of cyclohexane derivativesWeek 10:Cycloaddition reactions: Diels-Alder reactions, Hydroboration-Oxidation of alkenes,, Baeyer-Villiger Oxidation. Stereochemistry of Aldol condensation, Wittig reaction, Carbonyl addition reactionWeek 11:Stereochemistry of Molecular rearrangements: Pinacol rearrangement, Hoffman, Curtius, Schmidt and Lossen rearrangemnet, Beckmann, Wolff Rearrangement, Cope, Claisen rearrangementWeek 12:Introduction to crystallographic symmetry: 1D symmetry, Concept of 2D symmetry and lattices, notations of symmetry elements, space groups in 2D, 3D lattices, 32 point groups and their notations, crystal systems and Bravais lattices
Taught by
Prof. Angshuman Roy Choudhury
