CH 401 (C) : Organic Reactions


Classification of reactions :

A brief introduction to substitution, elimination, addition, oxidation, reduction, rearrangement and pericyclic reactions.Functional group transformations:alcohols to alkylating agents, Mitsunobu and related reactions, introduction of functional groups by nucleophilic substitution at saturated carbon, nucleophilic cleavage of C-O bonds in ethers and esters and inter-conversion of carboxylic acid derivativesOxidation:Metal based oxidizing reagents: A review and detailed discussion of chromium, manganese, ruthenium, silver and other metal based reagents. Non-metal based oxidizing reagents: DMSO, peroxide, peracid and oxygen based oxidation. Miscellaneous oxidizing reagents like IBX, DMP, CAN, DDQ, periodate etc.Reduction:Homogeneous and heterogeneous; Discussion on borane based racemic and chiral reagents, hydrogenations aluminium, tin, silicon based reducing agents. Dissolving metal reductions.Selectivity and protecting groups:Illustration of chemoselectivity, regioselectivity and stereoselectivity with examples; protecting groups for alcohols, amines, acids, ketones and aldehydes.Cycloaddition reactions:Diels-Alder reaction; general features, dienes, dienophiles, selectivity, intramolecular and intermolecular reactions, hetero-Diels Alder reaction. 1,3-dipolar cycloaddition reactions; general features, dipoles, dipolarophiles. [2+2] cycloaddition reactions; general features, selected examples.Molecular rearrangements:Illustration of electron deficient and electron rich skeletal rearrangements with examples; Sigmatropic rearrangements-Claisen and related rearrangments, Cope and oxy-Cope rearrangements; 2,3-sigmatropic rearrangements and ene reaction.

Text References

  1.  Jerry March, “Advanced Organic Chemistry”, Fifth Ed., Wiley, 2007.
  2.  F. A. Carey and R. J. Sundburg, “Advanced Organic Chemistry, Part B”, Fifth Ed., Plenum Press, 2007.
  3.  J. Clayden, N. Greeves, S. Warren and P. Wothers, “Organic Chemistry”, First Ed., Oxford University Press, 2001.
  4. W. Carruthers, “Some Methods of Organic Synthesis”, Cambridge University Press,
  5. K. Peter C. Vollhardt and Neil E. Schore “Organic Chemistry” W. H. Freeman and Company, 1999.