SYLLABUS

B.Sc. Paper II ORGANIC CHEMISTRY

Unit-I

1. Structure and Bonding:

Hybridization, bond lengths and bond angles, bond energy, localized and delocalized chemical bonding, van der Waals interaction, inclusion compounds, clatherates, charge transfer complex, resonances, hyperconjugation, aromaticity, inductive and field effects, hydrogen bonding.

2. Mechanism of Organic Reactions

Curvedarrow notation, drawing electron movements with allows, halfheaded and double headed arrows, homolytic and heterolytic bond fission, types of reagents-electrophiles and nucleophiles, Type 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 anaysis, intermediates, isotope effects, kinetic and stcreochemical studies.)

3. Alkanes and Cycloalkanes

IUPAC nomenclature of branched and unbranched alkanes. the alkyl group, classification of carbon atom in alkanes, isomerism in alkanes, sources methods of formacion (with pocial reference to Wurtz reaction, Kolbe reaction Corey-House reaction and decarboxviation of carboxylic acids), physical properties and chemical reactions of alkanes, Mechanism of true radical halogenation of alkanes orientation, reactivity and selectivity Cyclcalkanes - Nomenclature inethods of formation, chemical reactions, Bacyer's strain theory and its limitations Ring strain in sınall rings (cyclopropane and cyclobutane), theor of strain less rings. The case of cyclopropane ring, banana bonds

Unit-II

4. Stereochemistry of Organic Compounds :

Concept of isomerism. Types of isomerism, Optical isomierism - clements of symmetrymolecular chirality, enantiomers. stercogenic center optical activity properties of enantiomers, chiral and achiral molecules with two stereogenic centers, disasteromers, thrco and erythro diastereomets, meso compounds. resolution of enantionmer, inversion, retention and recemization Relative and absolute configuration, sequence rules, D & I. and R&S systems of nomenclature Geometric isomerism - determination of configuration of geometric isomers. E & 2 system of nomenclature, geometric isomerism in oximes and alicyclic compounds Conformational isomerism - conformational analysis of ethane and n-butane, conformations of cyclohexanc, axial and cquatorial bonds, conformation of mono substituted cuclohexane derivatives, Ncwman projection and Sawhorse formulac Fischer and flying wedge formulac. Difference between configuration and conformatın

Unit-III

5. Alkenis, Cycloalkenes, Dienes and Alkynes:

Nomenclature of alkenes, methods of formation. mechanisms of dehydration of alcohols and dchydrohalogenation of alkyl halids, regioselectivity in alcohol dehydration. The Saytzeff rule, Holmann elimination, physical properties and relative stabilities of alkenes. Chemical reactions of alkenes - mechanism involved in hydrogenation, electrophilic and free radical additions. Markownikofl's rule, hydroborationoxidation, Oxymcrcuration: reduction. Epoxidation, ozonolysis, hydration, inydroxylation and oxidation with KMnO₂ Polymerization of alkencs, 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 dicnes: isolated, conjugated and cumulated dicnes. Structure of allenes and butadiene, inethods 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, hydroborationoxidation, metal-aminonia reductions, oxidation and polymerization.

Unit-IV

6. Arenes and Aromaticity :

Nomenclature of benzene derivatives. The aryl group, Aromatic nucleus and side chain. Structure of benzene: molecular formula and kekule structure, stability and carbon-carbon bond lengths of benzene, resonance s.ructure. MO picture.

Aromaticity : The Hucklc rule, aroinatic ions.

Aromatic clectrophilic substitution - general pattern of the mechanism, role of o and complexes, Mechanism of nitration, halogenation, sulphonation, mercuration and FriedelCrafts reaction Energy profile diagrams. Activating and deactivating substituents, orientation and ortho/para ratio, Sidc chain reactions of benzene derivatives. Birch reduction. Methods of formation and chemical reactions of alkylbenzenes. alkynylbenzenes and biphenyl, naphthalene and Anthracene:

7. Alkyl and Aryl Ilalides :

Nomenclature and classes of alkyl halides, methods of formation, chemical reactions, Mechanisms of nucleophilic substitution rcactions of alkyl hallides, S, 2 and I reactions with energy profilc 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 nuclcophilc aromatic substitution reactions:

Relative reactivities of alkyl halides vs allyl, vingl and aryl halides, Synthesis and uses of DDT and BHC.

CONTENTS

1. Structure and Bonding ... 1-41

2. Organic Reactions ... 42-88

3. Stereo Chemistry of Organic Compounds ... 89-146

4. Alkenes ... 147-177

5. Cycloalkanes ... 178-194

6. Alkenes or Olefins ... 195–250

7. Alkynes ... 251-274

8. Cycloalkanes and Alkadienes ... 277–299

9. Alkyl Halides and Polyhalogen Compounds ... 300-332

10. Aromatic Hydrocarbon ... 333-371

11. Aromatic Substitution ... 372-406

12. Polynuclear Hydrocarbons ... 407-435

13. Aryl Halides ... 436-458