Course Details
Subject {L-T-P / C} : CY4101 : Stereochemistry and Reaction Mechanism { 3-1-0 / 4}
Subject Nature : Theory
Coordinator : Prof. Gokarneswar Sahoo
Syllabus
Dynamic stereochemistry: Stereoselective Reactions, Asymmetric Induction in synthetic reactions, Acyclic Stereoselection – Considerations to Carbonyl additions- 4membered and 6-membered transition states, Cram, Karabatsos, Felkin and Cieplak Models, Stereoelctronic Use of Chiral Auxilliaries in Carbonyl additions and enolate alkylation- Evans auxilliary, asymmetric induction, Enantioselective Hydroboration, Chiral Metalloenamines. Addition to enolates, Zimmermann-Traxler transition state.
Reaction Mechanism: Methods of determining reaction mechanisms, Prediction of Probable Products – Kinetic vs Thermodynamic Control, Hammond postulate, Curtin Hammett principle, Kinetic isotope effect, Baldwin rules for ring closure. Effect of structure and medium on reactivity, Substituent Effects, Hammett Plots and Linear Free Energy Relationships, Other Linear Free Energy Relationship, Acid-Base Related Effects, Substitution Reactions: SN1, SN2, SNi, SN1’, SN2’ reactions, reactivity, solvent effect, nature of bases, effects of leaving groups. Neighboring Group participation, Nonclassicalcarbocations, Phase transfer catalysis. Ring expansion and ring Contraction reactions, Aromatic electrophilic substitution reaction, Aromatic nucleophilic substitution reaction, Addition Reactions: Addition to carbon-carbon multiple bonds, addition to carbon-hetero multiple bonds Elimination reactions: E2, E1 E1cB, regioselectivity and stereoselectivity of the double bond, Reactivity in elimination reactions, Pyrolytic eliminations (Chugaev Elimination, Hoffmann degradation, cope reaction).
Course Objectives
- To understand and focus on the dependency of reaction outcomes on stereochemical relationship of the molecules
- To be able to visualize complex molecules three dimensionally
Course Outcomes
1)This course gives the understanding about the three dimensional arrangement of organic molecules and and their reactivity profile. <br />2) This course also delivers the understanding how and which organic molecules react with each other to give a different product(s).
Essential Reading
- D. Nasipuri, Stereochemistry of Organic Compounds, New Age International Publishers
- E.L.Eliel, Stereochemistry of Organic Compounds, Wiley
Supplementary Reading
- Subrata Sengupta, Stereochemistry of Organic Molecules, Book Syndicate Pvt. Ltd
- M M Smith, Organic Synthesis, Mc Graw Hill