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Available courses

Organic Chemistry II

SEMESTER V

CORE VII ORGANIC CHEMISTRY II

Course Objectives

Ø  The primary objectives of this course are to

Ø  Learn about stereochemistry and conformational analysis

Ø  Study amino acids and carbohydrates

Ø  Understand aromaticity and study reactions of aromatic compounds

Ø  Gain Knowledge on Heterocyclic compounds

UNIT I OPTICAL ISOMERISM

Representation of molecules in saw horse, Fischer, flying-wedge and Newman formulae and their inter translations.

Symmetry elements - chirality – asymmetric molecules and molecular dissymmetry-pseudo asymmetry.

Optical rotation – specific rotation –optical purity – racemisation (through cationic and anionic and radical intermediates), resolution of acids, bases and alcohols via diastereomeric salt formation.

Optical isomers - enantiomers – diastereomers – epimers - notation of optical isomers - Cahn-Ingold-Prelog rules, R and S notations for optical isomers with one and two asymmetric carbon atoms - erythro and threo representations - D and L representations

Optical activity in compounds without asymmetric carbon atoms namely biphenyls, allenes and spiranes. Stereo selectivity – stereo specificity – partial asymmetric synthesis. point,dipole moment – chemical method – dehydration and cyclisation.

UNIT II GEOMENTRICAL ISOMERISM AND CONFORMATIONAL ANALYSIS

Geometrical isomerism – nomenclature of geometrical isomers – cis – trans ,E-Z notation and syn-anti for C=C,C=N compounds. Methods to assign configurations.

Stability of geometrical isomers and heats of hydrogenation.

Tautomerism: Keto – enol Tautomerism, Amido – imido Tautomerism, Amino – imino Tautomerism.

Conformational analysis of ethane, propane, n-butane, haloethane, 1,2-dihaloethane,

1,2-glycol and 1,2-halohydrin, cyclopentane. Relative stability of conformers on the basis of steric effect, dipole-dipole interaction, H-bonding.

UNIT III AMINOACIDS AND CARBOHYDRATES

Amino acids - classification, general methods of preparation and reactions of amino acids, zwitter ion - isoelectric point, action of heat.

Classification-Monosaccharides- constitution of glucose and fructose. Reactions of glucose and fructose – Osazone formation, Mutarotation, cyclic structure, pyronose and furanose forms. Epimerisation- Interconversions of aldoses and ketoses.

Disaccharides- sucrose- reactions ( elucidation of structure not necessary).

Polysaccharides – starch and cellulose ( elucidation of structure not necessary).

UNIT IV AROMATICITY AND AROMATIC SUBSTITUTION

Aromaticity – definition – Huckel‟s rule– stability, carbon-carbon bond lengths of benzene, resonance energy Benzenoid and Non-benzenoid aromatic compounds

Aromatic electrophilic substitution – Mechanism of nitration, halogenation, sulphonation and Friedel-Crafts reaction. Activating and deactivating substituents, orientation in mono substituted benzenes, ortho/para ratio- Orientation- Korner‟s absolute method, dipole moment method – direct influence of substituents – rules of orientation - Aromatic Nucleophilic substitutions- unimolecular, bimolecular and benzyne mechanisms

UNIT V HETEROCYLIC COMPOUNDS

Molecular orbital picture and aromatic characteristics of pyrrole,furan, thiophene and pyridine. Comparison of basicity of pyridine, piperidine and pyrrole.

Methods of synthesis and chemical reactions with particular emphasis on the mechanism of electrophilic substitution and nucleophilic substitution reaction in pyridine derivatives.

Preparation and reactions of indole, quinoline and isoquinoline with special reference to Fisher indole synthesis, Skraup synthesis and Bischler-Nepieralski synthesis, mechanism of electrophilc substitution reactions of indole, quinoline and isoquinoline.

Text Books

1.K.S. Tewari, N.K. Vishnoi, S.N. Mehrotra. A Text Book of Organic Chemistry, Vikas publishing house (P) Ltd. 2002.

2.Arun Bahl and B. S. Bahl Advanced Organic chemistry, S. Chand and Company Ltd.,

Reprint2005

3. P.L. Soni, Text Book of Organic chemistry, Sultans chand, New Delhi, 1991

Reference Books

1. Ernest l. Eliel, Stereochemistry of Organic compounds,Tata McGraw –Hill Publication company Ltd., New Delhi,1975

2. D. Nasipuri, Stereochemistry of Organic Compounds - Principles and Applications, New Age International Publishers,1994

3. P. S. Kalsi, Stereochemistry -Conformation and Mechanism, New Age International Publishers,1994

4. R. T. Morrison and R. N. Boyd, Organic Chemistry, 6th Edition, PHI Limited, New Delhi, 1992.

5. Bhupinder Mehta, Manju Mehta, Organic chemistry, PHI Learning pvt. Ltd.,2005.