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ADVANCED PHARMACEUTICAL ORGANIC CHEMISTRY – I



Stereochemistry: Elements of symmetry-plane of symmetry, center of symmetry, alternating axis of symmetry and simple axis of symmetry. Nomenclature – D, L and R, S- nomenclature, sequence rules, kinds of molecules displaying optical activity. Stereochemistry of biphenyls, allenes and spiranes. Cis/Trans, E-Z isomerism resulting from double bonds, monocyclic compounds, fused ring systems. Racemic modifications and methods of resolution of racemic mixtures. Asymmetric Synthesis and stereoselective synthesis.


Reactive Intermediates: Definition, generation, stability, structure and reactivity of free radicals, carbocations, carbanions, carbenes, nitrenes/ nitrenium ions.

Mechanisms of Organic Reactions: Electrophilic (addition and substitution), Nucleophilic (addition and substitution), elimination and free radical (addition and substitution) reactions.

Pericyclic Reactions: Electrocyclic, cycloaddition and sigmatropic reactions-introduction, terminology and mechanism with suitable examples.


Molecular Rearrangements: 
            1. Carbon to carbon migration: Wagner- Meerwin rearrangement, Claisen rearrangement, Pinacol-pinacolone rearrangement and Benzil- benzilic acid rearrangement. 
            2. Carbon to nitrogen migration: Hoffmann rearrangement, Curtius rearrangement, Beckmann rearrangement and Lossen rearrangement. 
            3. Carbon to oxygen migration: Bayer- Villager rearrangement and rearrangement of hydroperoxides.

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