PHARMACEUTICAL ORGANIC CHEMISTRY

SYLLABUS OF FIRST YEAR PHARM D 

PHARMACEUTICAL ORGANIC CHEMISTRY

CHAPTERS-16

Structures and Physical properties: 

      a. Polarity of bonds, polarity of molecules, M.P, Inter molecular forces, B.P, Solubility, non ionic solutes and ionic solutes, protic and aprotic Solvents, ion pairs, 

      b. Acids and bases, Lowry Bronsted and Lewis theories

      c. Isomerism 

Nomenclature of organic compound belonging to the following classes

      Alkanes, 

      Alkenes, 

      Dienes,

      Alkynes,

      Alcohols,

      Aldehydes, 

      Ketones,

       Amides,

       Amines, 

       Phenols, 

       Alkyl Halides,

       Carboxylic Acid, 

       Esters, 

       Acid Chlorides

       Cycloalkanes. 

 Free radicals chain reactions of alkane 

     Mechanism, 

     Relative reactivity 

     Stability

 Alicyclic compounds 

     Preparations of cyclo alkanes, 

     Bayer strain theory 

     Orbital picture of angle strain.

Nucleophilic aliphatic substitution mechanism

      Nucleophiles and leaving groups,

      Kinetics of second and first order reaction, 

      Mechanism and kinetics of SN2 reactions.

      Stereochemistry and steric hindrance,

      Role of solvents,

      Phase transfer catalysis, 

     Mechanism and kinetics of SN1 reactions, 

     Stereochemistry, carbocation and their stability, 

     Rearrangement of carbocation, 

     Role of solvents in SN1 reaction, 

     Ion dipole bonds, 

      SN2 versus SN1 solvolyses, 

     Nucleophilic assistance by the solvents.

Dehydro halogenation of alkyl halides

     1,2 elimination,

     Kinetics of E2 and E1 mechanism,

     Elimination via carbocation, 

     Evidence for E2 mechanism, 

     Absence of rearrangement isotope effect, 

     Absence hydrogen exchange, 

     The element effect, 

     Orientation and reactivity,

      E2 versus E1, 

      Elimination versus substitution, 

      Dehydration of alcohol, 

      Ease of dehydration, 

      Acid catalysis, 

      Reversibility, orientation. 

Electrophilic and free radicals addition

     Reactions at carbon-carbon, double bond, electrophile, hydrogenation, heat of hydrogenation and stability of alkenes, 

     Markownikoff rule,

      Addition of hydrogen halides, 

      Addition of hydrogen bromides, 

      Peroxide effect, 

       Electrophilic addition, mechanism, rearrangement, absence ofhydrogen exchange, orientation and reactivity, addition of halogen, mechanism,halohydin formation, 

       Mechanism of free radicals addition, 

      Mechanism of peroxide initiated addition of hydrogen bromide,

      Orientation of free addition, 

      Additions of carbene to alkene, 

     Cyclo addition reactions. 

Carbon-carbon double bond as substituents

        Free radical halogenations of alkenes, 

        Comparison of free radical substitution with free radical addition, 

        Free radical substitution in alkenes, 

        Orientation and reactivity, 

        Allylic rearrangements. 

Theory of resonance

        Allyl radical as a resonance hybrid, Stability, orbital picture, resonance stabilisation of allyl radicals, 

        Hyper conjugation,

        Allyl cation as a resonance hybrid, 

        Nucleophilic substitution in allylic substrate, 

        SN1 reactivity, 

        Allylic rearrangement, 

        Resonance stabilization of allyl cation, 

        Nucleophilic substitution in allylic substrate,

       SN2 nucleophilic substitution in vinylic substrate, vinylic cation, stability of conjugated dienes, resonance in alkenes, ease of formation of conjugated dienes, orientation of elimination, 

        Electrophilic addition to conjugated dienes, 

       1,4- addition, 

       1 ,2-versus 1,4-addition, 

        rate versus equilibrium, orientation and reactivity of free radical addition to conjugated dienes. 

Electrophilic aromatic substitution

       Effect of substituent groups, 

       Determination of orientation, 

       Determination of relative reactivity, 

       Classification of substituent group,

       Nitration,

       Sulphonation, 

       Halogenation, 

       Friedel craft alkylation,

       Friedel craft acylation, 

       Reactivity and orientation, 

       Activating and deactivating O,P,M directing groups,

       Electron release via resonance, 

       Effect of halogen on electrophilic aromatic substitution in alkyl benzene, 

       Side chain halogenation of alkyl benzene, 

       Resonance stabilization of benzyl radical. 

Nucleophilic addition reaction

      Mechanism,

      Ionisation of carboxylic acids, 

      Acidity constants, 

      Acidity of acids, 

      Structure of carboxylate ions, 

      Effect of substituent on acidity, 

      Nucleophilic acyl substitution reaction, 

      Conversion of acid to acid chloride, esters, amide and anhydride. 

       Role of caboxyl group, 

       Comparison of alkyl nucleophilic substitution with acyl nucleophilic substitution. 

Name Reactions- Aldehydes and Ketones (Mechanism)

       Aldol condensation,

      Claisen condensation, 

      Cannizzaro reaction, 

      Crossed aldol condensation, 

      Crossed Cannizzaro reaction,

      Benzoin condensation,

      Perkin condensation.

      Knoevenagel reaction, 

      Reformatsky reaction, 

      Wittig reaction, 

      Michael addition.

Name reactions-Phenols and Amines(Mechanism)

      Hoffman rearrangement, 

      Migration to electron deficient nitrogen, 

      Sandmeyer’s reaction, 

      Basicity of amines, 

      Diazotization and coupling,

      Acidity of phenols, 

      Williamson synthesis, 

      Fries rearrangement, 

      Kolbe reaction, 

      Reimer tieman’s reactions. 

Nucleophilic aromatic substitution

 Bimolecular displacement mechanisms, orientation, comparison of aliphatic nucleophilic substitution with that of aromatic. 

Oxidation reduction reaction. 

 Study of the following official compounds

     Preparation, test for purity, assay and medicinal uses of 

         Chlorbutol, 

         Dimercaprol, 

         Glyceryl trinitrate, 

          Urea,  

          Ethylene diamine dihyrate,  

          Vanillin, 

          Paraldehyde, 

          Ethylene chloride,

          Lactic acid, 

          Tartaric acid, 

          Citric acid, 

          Salicylic acid, 

          Aspirin, 

          Methyl salicylate, 

          Ethyl benzoate, 

          Benzyl benzoate,    

          Dimethyl pthalate,  

          Sodium lauryl sulphate,  

          Saccharin sodium, 

         Mephensin.