1.4 Pharmaceutical Organic Chemistry Pharm D Syllabus, Notes, PDF, Books, Downloads
Pharmaceutical Organic Chemistry Theory
1 Structure and Physical properties:
a. Polarity of bonds, the polarity of molecules, M.P, Intermolecular 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
2 Nomenclature of organic compounds belonging to the following classes
Alkanes, Alkenes, Dienes, Alkynes, Alcohols, Aldehydes, Ketones, Amides, Amines, Phenols, Alkyl Halides, Carboxylic Acid, Esters, Acid Chlorides And Cycloalkanes.
3 Free radicals chain reactions of alkane: Mechanism, relative reactivity, and stability
4 Alicyclic compounds: Preparations of cyclo alkanes, Bayer strain theory, and orbital picture of angle strain.
5 Nucleophilic aliphatic substitution mechanism:
Nucleophiles and leaving groups, the kinetics of the second and first-order reaction, mechanism, and kinetics of SN2 reactions. Stereochemistry and steric hindrance, the role of solvents, phase transfer catalysis, mechanism and kinetics of SN1 reactions, stereochemistry, carbocation and their stability, rearrangement of carbocation, the role of solvents in an SN1 reaction, Ion dipole bonds, SN2 versus SN1 solvolyses, nucleophilic assistance by the solvents.
6 Dehydro halogenation of alkyl halides:
1,2 elimination, kinetics, E2 and E1 mechanism, elimination via carbocation, evidence for E2 mechanism, absence of rearrangement isotope effect, absence of hydrogen exchange, the element effect, orientation and reactivity, E2 versus E1, elimination versus substitution, dehydration of an alcohol, ease of dehydration, acid catalysis, reversibility, orientation.
7 Electrophilic and free radicals addition:
Reactions at carbon-carbon, double bond, electrophile, hydrogenation, the heat of hydrogenation and stability of alkenes, markownikoff rule, the addition of hydrogen halides, the addition of hydrogen bromides, peroxide effect, electrophilic addition, mechanism, rearrangement, absence of hydrogen exchange, orientation and reactivity, the addition of halogen, mechanism, halohydin formation, mechanism of free radicals addition, mechanism of peroxide initiated the addition of hydrogen bromide, the orientation of free addition, additions of carbene to an alkene, cyclo addition reactions.
8 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.
9 Theory of resonance:
Allyl radical as a resonance hybrid, stability, orbital picture, resonance stabilization of allyl radicals, hyperconjugation, allyl cation as a resonance hybrid, nucleophilic substitution in an allylic substrate, SN1 reactivity, allylic rearrangement, resonance stabilization of allyl cation, hyperconjugation, nucleophilic substitution in an allylic substrate, SN2 nucleophilic substitution in a vinylic substrate, vinylic cation, stability of conjugated dienes, resonance in alkenes, hyperconjugation, ease of formation of conjugated dienes, the 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.
10 Electrophilic aromatic substitution:
Effect of substituent groups, determination of orientation, determination of relative reactivity, classification of a substituent group, mechanism of nitration, sulphonation, halogenation, Friedel craft alkylation, Friedel craft acylation, reactivity, and orientation, activating and deactivating O, P, M directing groups, electron release via resonance, the effect of halogen on electrophilic aromatic substitution in alkyl benzene, side chain halogenation of alkyl benzene, resonance stabilization of benzyl radical.
11 Nucleophilic addition reaction:
Mechanism, ionization of carboxylic acids, acidity constants, the acidity of acids, the structure of carboxylate ions, the effect of substituent on acidity, nucleophilic acyl substitution reaction, conversion of acid to acid chloride, esters, amide, and anhydride. Role of the carboxyl group, comparison of alkyl nucleophilic substitution with acyl nucleophilic substitution.
12 Mechanism of aldol condensation, claisen condensation, Cannizzaro reaction, crossed aldol condensation, crossed Cannizzaro reaction, benzoin condensation, perkin condensation. Knoevenagel, Reformatsky reaction, Wittig reaction, Michael addition.
13 Hoffman rearrangement:
Migration to electron-deficient nitrogen, Sandmeyer’s reaction, the basicity of amines, diazotization and coupling, the acidity of phenols, Williamson synthesis, Fries rearrangement, Kolbe reaction, Reimer Tieman’s reactions.
14 Nucleophilic aromatic substitution:
Bimolecular displacement mechanisms, orientation, comparison of aliphatic nucleophilic substitution with that of aromatic.
15 Oxidation-reduction reaction.
16 Study of the following official compounds– preparation, test for purity, assay, and medicinal uses of Chlorbutol, Dimercaprol, Glyceryl trinitrate, Urea, Ethylene diamine dihydrate, Vanillin, Paraldehyde, Ethylene chloride, Lactic acid, Tartaric acid, citric acid, salicylic acid, aspirin, methyl salicylate, ethyl benzoate, benzyl benzoate, dimethyl phthalate, sodium lauryl sulfate, saccharin sodium, mephensin.
Pharmaceutical Organic Chemistry Practical
I. Introduction to the various laboratory techniques through demonstration involving synthesis of the following compounds (at least 8 compounds to be synthesized):
- Acetanilide / aspirin (Acetylation)
- Benzanilide / Phenyl benzoate (Benzoylation)
- P-bromo acetanilide / 2,4,6 – tribromo aniline (Bromination)
- Dibenzylidene acetone (Condensation)
- 1-Phenylazo-2-naphthol (Diazotisation and coupling)
- Benzoic acid / salicylic acid (Hydrolysis of ester)
- M-dinitro benzene (Nitration)
- 9, 10 – Antharaquinone (Oxidation of anthracene) / preparation of benzoic acid from toluene or benzaldehyde
- M-phenylene diamine (Reduction of M-dinitrobenzene) / Aniline from nitrobenzene
- Benzophenone oxime
- Nitration of salicylic acid
- Preparation of picric acid
- Preparation of O-chlorobenzoic acid from O-chlorotolune
- Preparation of cyclohexanone from cyclohexanol
II. Identification of organic compounds belonging to the following classes by Systematic qualitative organic analysis including the preparation of derivatives Phenols, amides, carbohydrates, amines, carboxylic acids, aldehyde and ketones, Alcohols, esters, hydrocarbons, anilides, nitro compounds.
III. Introduction to the use of stereo models:
Methane, Ethane, Ethylene, Acetylene, Cis alkene, Trans alkene, inversion of configuration.
First Year Pharm D Subjects Syllabus, Notes, PDF Books, MCQ
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