CH 401 : Organic Reactions
Syllabus
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 derivatives
Oxidation: 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
- Jerry March, “Advanced Organic Chemistry”, Fifth Ed., Wiley, 2007.
- F. A. Carey and R. J. Sundburg, “Advanced Organic Chemistry, Part B”, Fifth Ed., Plenum Press, 2007.
- J. Clayden, N. Greeves, S. Warren and P. Wothers, “Organic Chemistry”, First Ed., Oxford University Press, 2001.
- W. Carruthers, “Some Methods of Organic Synthesis”, Cambridge University Press,
- K. Peter C. Vollhardt and Neil E. Schore “Organic Chemistry” W. H. Freeman and Company, 1999.