JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY HYDERABAD

Course Objectives

The course structure is designed to give the knowledge of organic chemistry at

an advanced level and mainly aimed at the stereochemistry and different organic named reactions including preparations of reactive intermediates.

Course Outcome

The student would be in position to design a stereoselective synthesis of new

chemical entities (NCE) for the treatment of different diseases in new drug discovery Program.

UNIT - I

• a. Stereochemistry: a. Elements of symmetry, simple axis of symmetry. Notation, relative configuration and absolute configuration. Compounds with a chiral carbon atom, compounds with other quadrivalent chiral atoms. Optical isomerism in compounds containing no chiral atom, biphenyl, allenes, compounds with exocylic double bonds and spirans.
• b. Chirality due to helical shape.cis / trans, E – Z isomerism resulting from double bonds, monocyclic compounds, fused ring system. Racemic modifications and methods for resolution of racemic mixtures. Asymmetric synthesis and stereo – selective synthesis.

UNIT - II

• a. Reactive Intermediates: Definitions, generation, stability, structure and reactivity of free radicals carbocations, carbanions, carbenes, Nitrenes/Nitrenium ions.
• b. Concepts of aromaticity and antiaromaticity, non-benzenoid aromatic compounds.

UNIT - III

Mechanisms of organic reactions: Free radical, Electrophilic, Nucleophilic reactions of aliphatic and aromatic compounds

UNIT - IV

Elimination Reactions: E1, E2, E1CB and E2CB mechanisms, Mechanisms and orientation in pyrolytic eliminations, effect of substrate structure, attacking base, leaving group and reaction bond, medium and reactivity addition to carbon – carbon multiple bond reactions. Mechanisms, Orientation and reactivity.

UNIT - V

Electrocyclic, pericyclic and sigmotropic reactions: Introduction, terminology and mechanism, with suitable examples.

TEXT BOOKS:

• 1. Francis A. Carey & Richard J. Sunberg, Advanced Org. Chemistry, III rd Edition, Par B; Reactions and synthesis, Plenum Press, New York, London, Latest Edition.
• 2. Eliel I. Ernest and Samuel h, Stereochemistry of Org. Compounds, John Wiley and sons,.
• 3. Organic Chemistry, V Algarsamy, Pharmamed Press.
• 4. Roland E. Lehr & Alan P Marchard, Orbital Symmetry: A Problem-Solving approach, Academic Press, New York Latest Edition.
• 5. J. March, Advanced Org. Chemistry, Reactions Mechanisms and Structure, 4th
• 6. Edition, John Wiley & Sons, New York Latest Edition
• 7. I. L. Finar, Organic Chemistry, ELBS
• 8. Herbert O. Modern Synthesis Reactions IInd Edition W.A. Beenamis Inc. Menco Park California
• 9. W. Carruthers, Some Modern Methods of Org. Synthesis, III rd Edition, Cambridge University Press, Cambridge. M.Pharm I Year I Sem (Pharmaceutical Chemistry)