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Course 8. Engineering Chemistry 2 (Web Course)
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Prof. H. M. Chawla
Department of Chemistry
Indian Institute of Technology Delhi
Hauz Khas New Delhi -110 016
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Prof. R. N. Ram
Department of Chemistry
Indian Institute of Technology Delhi
Hauz Khas New Delhi -110 016
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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.