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Course 8. Engineering Chemistry 2 (Web Course) Faculty Coordinator(s) : 1. Prof. H. M. Chawla Department of Chemistry Indian Institute of Technology Delhi Hauz Khas New Delhi -110 016 Email : [email protected] Telephone : (011) Off : 26596599, 2685517 26591854, Res : 2. 26851860 Prof. R. N. Ram Department of Chemistry Indian Institute of Technology Delhi Hauz Khas New Delhi -110 016 Email : [email protected] Telephone : (011) Off : Res : 2659 1508, 2659 6599, 2685 1517 2659 1990, 2659 1854, 2685 1860, 26561247 Detailed Syllabus : ORGANIC CHEMISTRY 1. INTRODUCTION TO MOLECULAR STRUCTURE AND STEREOSTRUCTURE OF ORGANIC COMPOUNDS Structural and stereoisomerism. Representation of three dimensional structures on a plane, Newman, Fischer and Sawhorse formulae. Optical isomerism. Configuration, optical activity. Enantiomers, diastereomers, meso form, racemic modification. D&L, R&S and threo & erythro systems of naming stereoisomers. Determination of relative and absolute configurations. . Simple concepts in dynamic stereochemistry (inversion, retention, racemization and resolution). Geometrical isomerism. Cis & trans and E&Z nomenclature of geometrical isomers. Conformation conformational analysis of ethane, propane, butane and cyclohexane. Concepts of axial and equatorial bonds. Stability of different conformers of mono- and disubstituted cyclohexanes. Optical and geometrical isomerism of cyclohexane derivatives and simple bicyclic compounds. (Lectures 1-7) 2.REACTIVITY OF MOLECULES Electronic displacements, concepts of conjugation ,electron delocalization and resonance. Nature of reactions (polar and non-polar reactions). Factors affecting electron availability in a molecule. Strengths of organic acids and bases. Quantitative structure- reactivity relationship-Hammett eqution and its applications. Thermodynamic and kinetic requirements for a reaction to go to completion. Importance of kinetic parameters to establish mechanism of reaction- rates of reactions, steady state approximation, energy of activation, reaction coordinate-potential energy profiles, transition state, Hammond’s postulate. Concept of thermodynamic and kinetic control of reactions. (Lectures 8-12) (a) NUCLOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS Homolytic and heterolytic fission of bonds, formation and stability of carbanions, carbocations and free radicals. Nucleophiles and electrophiles. Substitution and elimination reactions, SN1, SN2, SNi, El and E2 mechanisms. Stereochemistry of E2 elimination. Effect of attacking and leaving groups and that of solvent polarity on mechanims. Neighbouring group participation. Hoffman and Saytzeff elimination. Substitution vs. elimination as a function of structure and strength of the base used. (Lectures 13-18) (b) ADDITION TO MULTIPLE BONDS Electrophilic addition to C=C bonds. Stereochemistry of electrophilic addition. 1,2 and 1,4-addition to conjugated dienes. Nucleophilic addition to carbonyl compounds – stereochemistry, Cram;s rule. Some important name reactions involving carbanion addition to carbonyl groups ( Aldol, Perkin, Michael reactions, Claisen ester condensation, etc.). Synthetic applications of active methylene compounds (malonic and acetoacetic esters). (Lectures 19-23) (c) ELECTROPHLIC AROMATIC SUBSTITUTION Aromatic character, Huckel’s rule. Electrophilic aromatic substitution (only upto disubstitution reactions), halogenation, sulphonation, nitration, Friedel Crafts Reactions. Nucleophilic aromatic substitution. (Lectures 20-23) (d) HETEROCYCLIC COMPOUNDS Nomenclature of simple heterocyclic compounds. Preparation, and properties of furan, pyrrole, thiophene and pyridine derivatives. (Lecture 24-27) 3. BIOMOLECULES Carbohydrates: Mono-, di-, and poly-saccharides (starch and cellulose). Proteins: Amino acids, peptides and proteins. Structure and function of proteins. Nucleic acids: Nucleosides, nucleotides and nucleic acids. Lipids: triglycerides, phospholipids and sterols. Waxes (Lectures 28-36) 4. POLYMERS Classification of polymers and polymerization. Addition and condensation polymerization, chain growth and step growth polymerisation. Free radical, cationic and anionic polymerization and their mechanisms. Initiators, inhibitors and chain transfer reagents. Coordination polymerization. Copolymers. Tacticity of polymers. Fibres, plastics and elastomers. Thermoplastic and thermosetting polymers. Some commercially important polymers. (Lectures 37-42) RECOMMENDED TEXT BOOKS 1. Text Book of Organic Chemistry, R. T. Morrison and R. N. Boyd, Prentice Hall ofIndia, New Delhi. 2. Guide book to Reaction Mechanism in Organic Chemistry, Peter Sykes, Longman, London. 3. Organic Chemistry: Vol I, I. L.Finar, Longrnan, London. 4. Organic Chemistry, S. N. Ege, AlTBS Publishers, Delhi. 5. Organic Chemistry, T. W.G. Solomons, John wiley & Sons, New York.