CH 220 : Reactions of carbonyl compounds


Nucleophilic Addition to CO group: MO aspects, Hydration and cyanohydrin reaction, thermodynamic Vs. Kinetic control, Organometallic reagents for C-C bond formation (organo lithium, magnesium and cerium compounds), ortholithiation, transmetallation, metal halogen exchange, Stereochemistry of nucleophilic addition to carbonyl group, Conjugate addition reactions.

Nucleophilic substitution at C=O: nature of leaving group, carbonyl reactivity, hydrolysis of esters, amides and nitriles, esterification, transesterification, conversion of acid into acid derivatives, making ketones and aldehydes from esters.

Nucleophilic substitution at C=O with the loss of carbonyl oxygen: acetals, cyclic acetals, thioketal, imines, enamines, reductive amination, alternative methods for amines formation, LAH reduction of amides, Strecker synthesis of amino acids, Wittig reaction

Enols, enolates and reactions: Alkylation, kinetic and thermodynamic enolates, Aldol reaction, specific enol equivalents (lithium enolate, aza enolate, silyl enol ether, enamines, zinc enolates), Knoevenagel reaction, Perkin reaction, Reformatsky reactions, Cannizaro reaction, Mannich reaction, intramolecular aldol reaction, Acylation, Claisen condensation, Dieckman cyclization, Conjugate addition of enolates, Robinsons Annulation

Chemoselectivity: chemoselective oxidation of alcohols to carbonyl compounds, chemoselective reduction of carbonyl compounds.

Retrosynthesis : Introduction to retrosynthetic analysis

Text References

  1. J. Clayden, N. Greeves, S. Warren and P. Wothers, “Organic Chemistry”, First Ed., Oxford University Press, 2001.
  2. K. P. C. Volhardt and N. E. Schore “Organic Chemistry: Structure and Function”, 5th Ed., W. H. Freeman and Company, 2007.
  3. L. G. Wade Jr. “Organic Chemistry”. 7th Ed., Prentice Hall, 2009.
  4. T. W. G. Solomons, C.G. Fryhle. “Organic Chemistry”, 9th Ed., Wiley-India, 2008.
  5. F. A. Carey and R. J. Sundburg, “Advanced Organic Chemistry, Part A&B”, 5th Ed., Plenum Press, 2007.