Pharm.D- PHARMACEUTICAL ORGANIC CHEMISTRY (THEORY)
Theory : 3 Hrs. /Week
1. Scope
and objectives:
This
course is designed to impart a very good knowledge about
a.
IUPAC/Common systems of nomenclature of simple organic compounds belonging to different
classes of organic compounds
b.
Some important physical properties of organic compounds
c.
Free radical/ nucleophylic [alkyl/ acyl/ aryl] /electrophylic- substitution,
free radical/ nucleophylic / electrophylic- addition, elimination, oxidation
and reduction reactions with mechanism, orientation, order of reactivity,
stability of compounds
d.
Some named organic reactions with mechanisms
e. Uses of organic compounds in pharmacy.
At the end of the course the student
should be able to
1.
name , write the structure of organic compound
2.
name the type of isomerism
3.
compare physical properties
4.
tell the name, class of reaction
5.
tell the method of conversion of
compounds
6.
account for reactivity, orientation of reactions
7.
prepare organic compounds
8.
identify, confirm the identification of organic compound
2.
Course materials:
Text books
a. Organic chemistry- T.R.Morrison and R. Boyd
b. Text book of
Pharmaceutical chemistry - Bentley and Driver
c. Organic chemistry, the
fundamentals of chemistry - I.L.Finar
d. Organic chemistry - P.L.Soni
e. Text book of organic
chemistry - B.S.Bahl and Arun Bahl
Reference books
a. Organic chemistry –
J.M.Cram and D.J.Cram
b. Organic chemistry-
Brown
c. Advanced organic
chemistry- Jerry March, Wiley
d. Organic chemistry-
Cram and Hammered, Pine Hendrickson
3. Lecture wise programme :
Note: To emphasise also
on definition, examples, uses in pharmacy, mechanisms of reactions
.
I. Classification and
Nomenclature
10 Hrs
Different types of
classification of organic compounds
i.
Common- IUPAC systems of nomenclature of
following classes of open chain compounds. Hydrocarbons, halohydrocarbons,
alcohols, aldehydes, ketones, carboxylic acids, carboxylic acid halides,
carboxylic acid amides, carboxylic acid esters, acid anhydrides, amines, ethers
ii.
Nomenclature of alicyclic compounds and
aromatic compounds (non heterocyclic)
II. Isomerism 04
Hrs
a. Structural
isomerism, chain isomerism, positional isomerism, functional isomerism,
metamerism, tautomerism
b. Stereo
isomerism, optical isomerism, geometrical isomerism, specification of
configuration, conformational isomerism
III. Structure and
Properties 05
Hrs
a.
Polar molecules, nonpolar molecules,
protic molecules, aprotic molecules
b.
Inter molecular forces
c.
Melting point, boiling point of organic
compounds, solubility of organic compounds
IV. Alkanes 03
Hrs
Free radical substitution reactions of
alkanes- reactivity, inhibition. Reaction between methane, ethane, propane and
halogens
V. Alkenes 08
Hrs
a.
i. Dehydrohalogenation reactions of alkyl halides- kinetics, rearrangement of
carbo cations, reactivity, orientation
ii.
Dehydration of alcohols reactions- kinetics, rearrangement of carbo cations,
reactivity, orientation
iii.
E1 versus E2 reactions
b. Electrophilic addition
reactions of alkenes- orientation, rearrangement of carbo cations, reactivity
c. Free radical addition
reactions of alkenes- orientation, reactivity
VI. Alkyl halides 03
Hrs
Preparation of alkyl halides from alcohols by
Nucleophylic substitution reactions, Nucleophylic substitution reactions of
alkyl halides- kinetics, reactivity, rearrangement of carbocations, solvent
effect, stereochemistry.
SN1 versus SN2 reactions
VII.
Alicyclic compounds 03 Hrs
a. Baeyer’s strain
theory, Sachse Mohr theory
b. General methods of
preparation
VIII. Dienes 03 Hrs
Classification,
stability, ease of formation of conjugated dienes, electrophilic and free
radical addition reactions of conjugated dienes
IX. Aromatic compounds 08 Hrs
a. Evidences
in the derivation of structure of Benzene, aromatic characters
b.
i. Electrophilic substitution reactions
of Benzene- nitration, sulfonation, halogenations, reactivity of halogens,
Friedel craft’s alkylation, reactivity of alkyl halides and limitation of
Friedel crafts alkylation reactions, Friedel crafts acylation reactions.
ii. Classification of substituents
iii. Orientation of mono substituted
Benzene compounds towards electrophylic substitution reactions.
c. Nucleophilic
aromatic substitution reactions- reactivity, comparison with aliphatic nucleophilic
substitution reactions
X. Carbonyl compounds 05 Hrs
a).
Nucleophilic addition reactions, reactions between carbonyl compounds and
hydrogen cyanide, Sodium bisulphite, hydroxyl amine, hydrazine, phenyl
hydrazine, 2,4- dinitro phenyl hydrazine, alcohol
b).
Aldol, crossed aldol, Cannizaro, crossed Cannizaro, Benzoin, Perkin reactions
XI. Carboxylic acids and
derivatives
05 Hrs
a).
Acidity of carboxylic acids and effect of substituents on it.
b).
Nucleophilic acyl substitution reactions, esterification.
c).
Comparison of alkyl nucleophilic substitution with nucleophilic acyl
substitution reactions
XII. Amines
03
Hrs
a.
Basicity of amines
b.
Hoffmanns degradation of amides, diazotization reactions, coupling reactions,
replacement reactions of aromatic diazonium salts
XIII. Phenols 03 Hrs
a.
Acidity of phenols
b.
Kolbe’s synthesis, Riemer tiemann reactions, pthalein reaction, Schotten Bauman
reaction, Libermann’s nitrosation reaction
XIV. Heterocyclic
compounds 04
Hrs
Classification,
nomenclature of mono and bicyclic compounds, medicinal uses of some important
heterocyclic compounds
XV. Carbohydrates 03 Hrs
Classification,
qualitative tests
XVI. Amino acids and
proteins 03 Hrs
a) Classification of
amino acids, qualitative tests for amino acids
b) Classification,
structure, colour reactions of proteins. Qualitative tests for proteins
1.4 PHARMACEUTICAL ORGANIC CHEMISTRY (PRACTICAL)
Practical: 3 Hours/week
1. Recrystallization
of organic compounds (1 exp)
2. Preparation
of simple non hetero cyclic organic compounds and recrystallisation of
compounds prepared. (Minimum
of 08 compounds)
i.
Aspirin/Benzanilide/Phenyl
benzoate/Acetanilide by acylation
ii.
2,4,6-Tribromo aniline/Para bromo
acetanilide by halogenation
iii.
5-Nitro salicylic acid/Meta di nitro
benzene by nitration
iv.
Dibenzal acetone from benzaldehyde by
Claisen Schmidt
v.
Benzoic acid from benzyl chloride by
oxidation
vi.
Benzoic acid/Salicylic acid by hydrolysis
vii.
1-Phenyl azo -2- napthol from aniline by
diazotization and coupling
viii.
Benzophenone oxime from benzophenone
3. Systematic
qualitative analysis of unknown organic compounds for preliminary and Lassaigns
tests. (
2 exp )
4. Systematic
qualitative analysis of unknown organic compounds for functional groups (for
preliminary / Lassaigns / solubility /
functional group tests )
Ø Following
classes of compounds may be analysed
Ø Phenols,
amide/ urea, carbohydrate, amine, carboxylic acid, aldehyde, ketone,
alcohol, carboxylic acid ester,
hydrocarbon, halohydrocarbon, nitrocompound, anilide 11
5. Determination
of melting and boiling points of organic compounds 1
6. Preparation
of suitable solid derivatives from organic compounds 1
7. Introduction
to the use of stereomodels – Methane,Ethane, Ethene, Acetylene, Cyclo
hexane, Benzene (Students to prepare the
ball and stick stereomodels using china clay, plastic sticks individually and
to explain the formation of bonds& bond angles, bond lengths)
Course Materials :
a. Practical
organic chemistry – Mann and Saunders
b. Introduction
to organic laboratory techniques – Pavia, Lampman, Kriz
c. Text
book of Practical Organic Chemistry - Vogel
Scheme of Practical Examination:
Sessional Annual
Synopsis 04
15
Major Experiment 12 25
Minor Experiment - 15
Viva 04 15
Max Marks 20 70
Duration 03hrs 04hrs
Note : Total sessional marks is 30 (20 for
practical sessional plus 10 marks for regularity, promptness, viva-voce and
record maintenance).
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