Bachler of Science Syllabus Detail
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B.SC I Year
Paper II CH-102 Organic Chemistry
I:Structure and Bonding
Hybridization, bond length and bond angles, bond energy, localized and delocalized chemical bond, Van der Waals interactions, clatherates, charge transfer complexes, resonance, hyperconjugation, aromaticity, inductive and field effects, hydrogen bonding.
II Mechanism of Organic Reactions
Curved arrow notation, drawing electron movements with arrows, half-headed and doubleheaded arrows, homolytic and heterolytic bond breaking. Types of reagents-electrophiles
and nucleophiles. Types of organic reactions, Energy considerations.
Reactive intermediates - carbocations, carbanions, free radicals, carbenes, arynes and nitrenes (with examples). Assigning formal charges on intermediates and other ionic species.
Methods of determination of reaction mechanism (product analysis, intermediates, isotope effects, kinetic and stereochemical studies).
III Stereochemistry of Organic Compounds
Concept of isomerism, types of isomerism.
Optical isomerism - elements of symmetry, molecular chirality, enantiomers, stereogenic centre, optical activity, properties of enantiomers, chiral and achiral molecules with two stereogenic centres, diastereomers, threo and erythro diastereomers, meso compounds, resolution of enantiomers, inversion, retention and racemization.
Relative and absolute configuration, sequence rules, D & L and R & S systems of nomenclature.
Geometric isomerism - determination of configuration of geometric isomers E & Z system of nomenclature, geometric isomerism in oximes and alicyclic compounds.
Conformational isomerism - conformational analysis of ethans and n-butane, conformations of cyclohexane, axial and equatorial bonds, conformation of mono substituted cyclohexane derivatives. Newman projection and Sawhorse formulae, Fischer and Flying wedge formulae. Difference between configuration and conformation.
IV Alkanes and Cycloalkanes
IUPAC nomenclature of branched and unbranched alkanes, the alkyl group, classification of carbon atoms in alkanes. Isomerism in alkanes, sources, methods of formation (with
special reference to Wurtz reaction, Kolbe's reaction, Corey-House reaction and decarboxylation of carboxylic acids), physical properties and chemical reactions of alkanes.
Mechanism of free radical halogenation of alkanes: orientation, reactivity and selectivity. Cycloalkanes- nomenclature, methods of formation, chemical reactions, Baeyer's strain theory and its limitations. Ring strain in small rings (cyclopropane and cyclobutane), theory of strainless rings. The case of cyclopropane ring: banana bonds.
V Alkenes, Cycloalkenes, Dienes and Alkynes
Nomenclature of alkenes, methods of formation, mechanisms of dehydration of alcohols and dehydrohalogenation of alkyl halides, regioselectivity in alcohol dehydration. The
Saytzeff rule, Hofmann elimination, physical properties and relative stabilities of alkenes.
Chemical reactions of alkenes -- mechanisms involved in hydrogenation. electrophilic and free radical additions. Markownikoff's rule, hydroboration-oxidation, oxymercurationreduction. Epoxidation, ozonolysis, hydration, hydroxylation and oxidation with KMnO4 Polymerization of alkenes. Substitution at the allylic and vinylic positions of alkenes. Industrial applications of ethylene and propene.
Methods of formation, conformation and chemical reactions of cycloalkenes.
Nomenclature and classification of dienes : isolated, conjugated and cumulated dienes. Structure of allenes and butadiene, methods of formation, polymerization. Chemical reaction --1, 2 and 1, 4 additions, Diels-Alder reaction.
Nomenclature, structure and bonding in alkynes. Methods of formation. Chemical reactions of alkynes, acidity of alkynes. Mechanism of electrophilic and nucleophilic addition reactions, hydroboration - oxidation, metal-ammonia reductions, oxidation and polymerization.
VI Arenes and Aromaticity
Nomenclature of benzene derivatives. Aryl group. Aromatic nucleus and side chain. Structure of benzene: molecular formula and Kekule structure. Stability and carbon-carbon
bond lengths of benzene, resonance structure, MO picture.
Aromaticity the Huckel rule, aromatic ions.
Aromatic electrophilic substitution--general pattern of the mechanism, role of σ - and π - complexes. Mechansim of nitration, halogenation, sulphonation, mercuration and Friedel-Crafts reaction. Energy profile diagrams. Activating and deactivating substituents, orientation and ortho/para ratio. Side chain reactions of benzene derivatives. Birch reduction.
Methods of formation and chemical reactions of alkylbenzenes, alkynylbenzenes and biphenyl.
VII Alkyl and Aryl Halides
Nomenclature and classes of alkyl halides, methods of formation, chemical reactions. Mechanisms of nucleophilic substitution reactions of alkyl halides, SN2 and SN1 reactions
with energy profile diagrams.
Polyhalogen compounds: chloroform, carbon tetrachloride.
Methods of formation of aryl halides, nuclear and side chain reactions.
The addition-elimination and the elimination-addition mechanisms of nucleophilic aromatic substitution reactions.
Relative reactivities of alkyl halides vs allyl, vinyl and aryl halides. Synthesis and uses of DDT and BHC.