PHARMACEUTICAL ORGANIC CHEMISTRY-I
SYLLABUS FOR I YEAR B.PHARMACY
STUDENTS FOR THE YEAR 2009-10

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JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY
ANANTAPUR.

PHARMACEUTICAL ORGANIC CHEMISTRY-I

UNIT – I
Structure and Activity of Organic Molecules: Shapes of organic molecules, bond lengths, bond angles and bond dissociation energies. Electronic effects in organic molecules: inductive effect, electromeric or mesomeric effect, hyperconjugation, concept of resonance; types of organic reagents and reactions.

UNIT – II
Study of Hydrocarbons:
Aliphatic/Alicyclic Hydrocarbons: Nomenclature, isomerism (chain, conformational and geometrical) relative stabilities (heats of combustion and hydrogenation), ring stabilities of cyclohexane, chair-boat conformation, Bayer’s strain theory and sachse-mohr theory. Free radical substitution reactions (halogenation) of alkanes, selectivity of halogens.
Alkenes: Electrophilic addition reactions of alkenes, Markovnikov’s rule, Anti-Markovnikov,s rule, Kharasch effect, Bayer’s oxidation (cis-hydroxylation, polymerisation).
Alkadienes: Stability & 1,4 addition reactions of conjugated alkadienes.
Alkynes: Acidity of 1-alkynes, formation of metal acetylides. Stereo specific reduction of alkynes. Addition of hydrogen halide (HCl) addition of water and keto-enol tautomerism.

UNIT – III
Aromatic Hydrocarbons: Kekule’s structure of benzene, bond lengths, heats of hydrogenation and stability, molecular orbital picture of benzene, aromaticity, Huckel’s rule, nomenclature of benzene derivatives, characteristic reactions of benzene, theory of reactivity and orientation in monosubstituted benzenes.

Polynuclear aromatic hydrocarbons: Nomenclature, structure and aromatic character of naphthalene, anthracene, phenanthrene and naphthacene resonance structures, electron density and reactivity. Electrophilic substitution, oxidation and reduction reactions.

UNIT – IV
Halogen Compounds-Aliphatic: Nomenclature, general methods of preparation, characteristic nucleophilic substitution reactions, factors that play role in SN1 and SN2, Walden inversion, elimination reaction and Saytzeff’s rule.
Halogen Compounds-Aromatic: Nomenclature, low reactivity of halo benzenes towards nucleophilic substitution, arenas, Benzyne ion concept..

UNIT – V
Alcohols: Nomenclature, classification, general methods of preparation, physical properties, hydrogen bonding, characteristic nucleophilic substitution reactions (replacement of -OH by -Cl), elimination reactions, and relative reactivities of 1o, 2o and 3o alcohols, Meerwein Pondorff Verley reduction.

Ethers: Nomenclature, Williamson’s synthesis, action of hydro iodic acid on ethers (Ziesel’s method).

Phenols: Nomenclature, general methods of preparation, physical properties, acidity of phenols, stability of phenoxide ion, reactions of phenols, Kolbe-schmidt reaction stability of conjugated dienes, and Fries rearrangement, Reamer-Tiemann Reaction.



UNIT – VI
Carbonyl Compounds: Nomenclature, two important methods of preparation, polarity of carbonyl group, relative reactivities of carbonyl compounds, nucleophilic addition and addition-elimination reactions, oxidation-reduction reactions, aldol condensation, Cannizzaro reaction, benzoin condensation, Perkins reactions, Reformatsky reaction, Oppenauer oxidation.

UNIT – VII
Carboxylic acids and their derivatives:
Carboxylic acids: Nomenclature, intermolecular association, stability of carboxylate anion, two important methods of preparation, decarboxylation, functional groups reactions, reduction of carboxylic acids.
Acid derivatives: (acid chlorides, anhydrides, esters and amides). Nomenclature, reactions like hydrolysis, reduction of esters and amides, Hofmann’s degradation of amides. Brief account of preparation and properties of malonic and acetoacetic esters, their importance in organic syntheses.

UNIT – VIII
Nitrogen Compounds:
Nitro compounds: Nomenclature, acidity of nitro compounds containing - hydrogens, reductive reactions of aromatic nitro compounds.
Amines: Nomenclature, basicity of amines, classification, relative reactivity, Hinsberg method of separation, acylation reactions. Diazotisation and reactions of diazonium salts.
Nitriles and isonitriles: Nomenclature, two methods of synthesis, reactivity and functional reactions.

TEXT BOOKS

1. Advanced pharmaceutical organic chemistry, Bahl & Bahl, S.Chand
2. Organic chemistry, T.R.Morrison and R.N.Boyd, Pearson Education India , New Delhi.

REFERENCES
1. Organic chemistry, Bruce,
2. Reactions and Mechanism, Jerry March, 4th ed
3. oragranic chemistry, Carey
4. oraganic chemistry, Pillai
5. The Fundamentals Principles of Organic Chemistry Vol.I & Vol. II, I.L. Finar, ELBS/Longman.