Syllabus

Syllabus (52-54 hours)
Substitution Reactions: SN1, SN2, SNi, SN1’, SN2’ reactions, reactivity, solvent effect, nature of bases, effects of leaving groups (4 hours)
Neighbouring Group participation, Nonclassical carbocations, Phase transfer catalysis. Ring expansion and ring Contraction reactions (5 hours)
Aromatic electrophilic substitution reaction, Aromatic nucleophilic substitution reaction (2 hours)
Addition Reactions: Addition to carbon-carbon multiple bonds (3 hours)
Addition to carbon-hetero multiple bonds (5 hours)
Elimination reactions: E2, E1 E1cB, regioselectivity and stereoselectivity of the double bond, Reactivity in elimination reactions, Pyrolytic eliminations (Chugaev Elimination, Hoffmann degradation, cope reaction) (6 hours)
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 (5 hours)
Stereoelectronic Use of Chiral Auxiliaries in Carbonyl additions and enolate alkylation- Evans auxilliary, asymmetric induction (2 hours)
Enantioselective Hydroboration, Chiral Metalloenamines. Addition to enolates, Zimmermann-Traxler transition state (2 hours)
Reaction Mechanism: Methods of determining reaction mechanisms, Prediction of Probable Products – Kinetic vs Thermodynamic Control, Hammond postulate, Curtin Hammett principle (3 hours)
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 (5 hours)
Problem (TA, GATE & NET) Discussion: (10-12 hours)

To understand and focus on the dependency of reaction outcomes on stereochemical relationship of the molecules

To be able to visualize complex molecules in three dimension.

To learn different aspects of stereoselective and stereospecific reactions

Study of reaction mechanism and nature of transition states.

1) This course gives the understanding about the three dimensional arrangement of organic molecules and and their reactivity profile.
2) This course also delivers the understanding how and which organic molecules react with each other to give different product(s).
3) The students would gain knowledge of devising reactions in regards to the stereochemical aspect of the reaction.
4) The course delivers information regarding the controlling factors in a reaction towards stereo-selectivity.
5) The students would learn comparing energy of different transition states/intermediates, towards a selective product formation.

D. Nasipuri, Stereochemistry of Organic Compounds, New Age International Publishers

E.L.Eliel, Stereochemistry of Organic Compounds, Wiley

Subrata Sengupta, Stereochemistry of Organic Molecules, Book Syndicate Pvt. Ltd

M M Smith, Organic Synthesis, Mc Graw Hill