Organic Chemistry-I (CHEM-372)

This course is designed to provide an understanding of the concepts that will be used in advanced organic chemistry courses. The course will be based upon a problem-solving approach in order to develop the ability to interpret and apply these concepts in advanced organic chemistry.

LEARNING OUTCOMES

This course will enable the students

to develop skills in naming organic compounds as per IUPAC rules.
to apply concepts of structure & reactivity in order to solve organic reactions/mechanisms problems.
to have an understanding of three-dimensional arrangement of atoms leading to the origin of different types of stereoisomerism in organic compounds.
to visualize and analyze the stereochemistry of organic molecules in organic reactions/mechanisms..

READINGS/BOOKS

Smith, M. and March, J., Advanced Organic Chemistry, Sixth Edition, John Wiley, New York (2007).
Pine, S. H., Organic Chemistry, McGraw-Hill, New York. (1980).
Clayden, Greeves, Warren and Wothers, Organic Chemistry, Oxford, London. (2001).
Gould, E. S., Mechanism and Structure in Organic Chemistry, Holt, Rinehart & Winston, New York. (1959).
House, H. O., Modern Synthetic Reactions, Benjamin, California. (1972).
Sykes, P., A Guide Book to Mechanism in Organic Chemistry, Longman Scientific and Technical, co-published with John Wiley, New York, (1985)
Solomons, T.W.G., Fryhle, C.B., Snyder, S.A., Organic Chemistry, 11th Edition, John Wiley, New York, (2014)

CONTENTS

Nomenclature: IUPAC nomenclature of polyfunctional aliphatic, alicyclic, aromatic, heterocyclic, multicyclic organic compounds, spiro and allenes.
Structure and reactivity: Inductive effect, resonance, hyperconjugation, aromaticity & tautomerism. The effect of structure, medium and steric factor on the strength of acids, bases and on acid-base equilibria. Introductory linear free energy relationship.
Stereochemistry of organic compounds: Configuration vs conformation. Wedge-head, Saw-horse, Newman & Fischer projections. Baeyer’s Strain theory, conformational isomerism in acyclic, alicyclic compounds (cyclobutane, cyclopentane, cyclohexane), mono / di-substituted cyclohexanes and condensed rings. Locking groups. Geometrical Isomerism: cis/trans, E/Z & syn/anti conventions. Optical Isomerism: Chirality and symmetry. Optical isomerism of compounds upto three asymmetric centers, Relative and absolute configuration (CIP rule & D/L, R/S, r/s, aR/aS conventions), Optical isomerism in biphenyls, allenes and spiro compounds. Racemization, resolution of racemic modification and introductory asymmertric synthesis. Stererospecificity vs stereoselectivity. Determination of configuration.

LESSON PLAN

Week 01	IUPAC nomenclature of polyfunctional aliphatic and alicyclic organic compounds.
Week 02	IUPAC nomenclature of polyfunctional aromatic, multicyclic, spiro organic compounds and allenes.
Week 03	IUPAC nomenclature of heterocyclic organic compounds..
Week 04	Inductive effect, Resonance, Hyperconjugation, Tautomerism.
Week 05	Aromaticity. The effect of structure on the strength of acids, bases and on acid-base equilibria.
Week 06	The effect of structure on the strength of acids, bases and on acid-base equilibria.
Week 07	The effect of medium and steric factor on the strength of acids, bases and on acid-base equilibria.
Week 08	Introduction to linear free energy relationships.
Week 09	MID TERM EXAMINATION
Week 10	Linear free energy relationships.
Week 11	Configuration vs conformation. Wedge-head, Saw-horse, Newman & Fischer projections. Baeyer’s Strain theory.
Week 12	conformational isomerism in acyclic, alicyclic compounds (cyclobutane, cyclopentane, cyclohexane), mono / di-substituted cyclohexanes and condensed rings. Locking groups.
Week 13	Geometrical Isomerism: cis/trans, E/Z & syn/anti conventions.
Week 14	Optical Isomerism: Chirality and symmetry. Optical isomerism of compounds upto three asymmetric centers, Relative and absolute configuration (CIP rule & D/L, R/S, r/s, aR/aS conventions)
Week 15	Optical isomerism in biphenyls, allenes and spiro compounds. Racemization, resolution of racemic modification
Week 16	Introductory asymmertric synthesis, Stererospecificity vs stereoselectivity
Week 17	Determination of configuration..
Week 18	FINAL TERM EXAMINATION