Organic Reaction Mechanisms
- To understand the basic concepts about organic reaction mechanisms.
- To learn the involvement of reactive intermediates, their structure and reactivity through various organic reactions, the orbital interactions (Woodward Hoffmann rules) in concerted reactions and apply knowledge for solving problems.
The student will
- got an idea about mechanisms involved in organic reactions.
- obtain knowledge about reaction intermediates.
- able to apply the concepts in solving and predicting the products of reactions.
Module 1: Review of Organic Reaction Mechanisms
1.1 Review of organic reaction mechanisms with special reference to nucleophilic and electrophilic substitution at aliphatic carbon (SN1, SN2, SNi, SE1, SE2), elimination (E1 and E2) and addition reactions (regioselectivity: Markovnikov’s additioncarbocation mechanism, anti-Markovnikov’s addition-radical mechanism). Elimination vs substitution.
1.2 A comprehensive study on the effect of substrate, reagent, leaving group, solvent and neighbouring group on nucleophilic substitution(SN2 and SN1) and elimination (E1and E2) reactions.
Module 2: Chemistry of Carbocations
3.1 Formation, structure and stability of carbocations. Classical and non-classicalcarbocations.
3.2 C-X bond (X = C, O, N) formations through the intermediary of carbocations. Molecular rearrangements including Wagner-Meerwein, Pinacol-pinacolone, Semipinacol, Dienone-phenol and Benzilic acid rearrangements, Noyori annulation, Prins reaction.
3.3 C-C bond formation involving carbocations: Oxymercuration, Halolactonisation.
Module 3 : Carbenes, Carbenoids, Nitrenes and Arynes
4.1 Structure of carbenes (singlet and triplet), generation of carbenes, addition and insertion reactions.
4.2 Reactions of carbenes such as Wolff rearrangement, Reimer-Tiemannreaction. Reactions of ylides by carbenoid decomposition
4.3 Structure, generation and reactions of nitrene and related electron deficient nitrene
4.4 Hoffmann, Curtius, Lossen, Schmidt and Beckmann rearrangement reactions.
4.5 Arynes: Generation, structure, stability and reactions. Orientation effect – amination