Course Title: 
Organic Reaction Mechanisms
Course Code: 
Year Taught: 
Undergraduate (UG)
School of Engineering

'Organic Reaction Mechanisms' is a course offered for the B. Tech. programs at the School of Engineering, Amrita Vishwa Vidyapeetham.

Unit 1

Introduction to organic chemistry: Lewis structure and formal charges of organic compounds - electro negativities and dipoles, resonances, aromaticity and anti aromaticity - equilibrium, tautomerism and hyper conjugation - acidity and basicity - pKa, nucleophiles and electrophiles - hydrogen bonding - different types of organic reaction - addition, substitution, elimination and rearrangement - oxidations and reductions - general principles of writing organic reaction mechanism - reactive intermediates.
Reaction of nucleophiles and bases: Nucleophilic substitution - SN1 and SN2 reactions, nucleophilic substitution at aliphatic sp2 carbon and aromatic carbon - nucleophilic addition to carbonyl compounds - addition of grignard and organo lithium reagents - reactions of nitrogen containing nucleophiles with aldehyde and ketones - aldol condensation.

Unit 2

Michael and 1,4-addition reaction - Favorskii rearrangement - benzilic acid rearrangement - reaction mechanism in basic media - Mannich reaction - enols and enolates.

Reaction involving acids and other eletrophiles: Carbocations - formation and rearrangements - cationic rearrangement involving electron deficient nitrogen atom - Beckmann rearrangement - Curtius, Lossen and Schmidt rearrangement - electrophilic additions - acid catalyzed reaction of carbonyl compounds - hydrolysis of carbocyclic acid derivatives - electrophilic aromatic substitution - carbenes and benzynes - Baeyer-Villeger reactions - Dienone-phenol rearrangement - pinacol rearrangement.

Unit 3

Radical and radical ions: Formation of radicals, radical chain processes, radical addition, reaction with and without cyclisation - fragmentation reaction - rearrangement of radicals - SRN 1 reaction - radical ions - Birch reduction - Hofmann-Loffler-Freytag reaction - Barton reaction - McMurry reaction.

Pericyclic reaction: Representative of molecular orbitals of ethylene, butadiene and hexatriene molecules - Woodward - Hofmann rules of symmetry - electrocyclic reaction, cycloadditions - diels-Alder reaction - other thermal cycloadditions - photochemical [2+2] cycloaddition - 1,3-dipolar cycloadditions - Sigmatropic reactions, notations and directions of [3,3] sigmatropic rearrangements - Cope and oxy-Cope rearrangement [2,3] sigmatropic reaction - ene reaction.

  • Jerry March, “Advanced Organic Chemistry”, 4th edition, John Wiley & Sons, (1992).
  • Carey F and Sundberg R, “Advanced Organic Chemistry - Part A & B”, Kluwer, (2000).
  • Peter Sykes, “Organic reaction mechanism”, 6th edition, Pearson education (Singapore) Pte. Ltd., (2005).
  • Michael B.Smith, “Organic Synthesis”, 2nd edition, McGraw Hill, (2004).