MSCCH 502

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Syllabus

M.Sc. (Chemistry) Programme


( SEMESTER – I )
Organic Chemistry – I
Programme Code- (MSCCH -21)
Course Code – (MSCCH -502 )

Block 1 Nature of Bonding in Organic Molecules


Unit 1: Nature of Bonding in Organic Molecules
Delocalized chemical bonding: conjugation, cross-conjugation, resonance, hyper conjugation,
tautomerism, Energy levels of 𝜋 orbitals, Huckel’s rule, aromaticity, anti-aromaticity and homo-
aromaticity, benzenoid and non-benzonoid aromatic compounds, alteranant and non-alteranant
hydrocarbons. Annulenes. Non-covalent bonding – addition compounds, crown ether complexes,
cryptands, inclusion compounds, catenanes, rotaxanes and ionic liquids.

Unit 2: Structure and Reactivity


Types of reaction mechanisms, types of reactions, kinetic and thermodynamic control,
Hammond’s postulate, Curtin-Hammond principle. Reaction co – ordinate, potential energy
diagrams, transition states and intermediates. Methods of determining mechanisms, isotopes
effects.
Unit 3: Reactive Intermediates
Generation, structure, stability and reactivity of carbocations, carbanions, carbon radicals, singlet
and triplet carbenes and nitrenes. Effect of structure on reactivity: resonance and field effects,
steric effects and quantitative treatment. The Hammett equation and linear free energy
relationships, substituent and reaction constants, Taft equation.
Block 2: Stereochemistry
Unit 4: Stereochemistry 1
Stereogenicity, chirality and prochirality, Enantiomerism, Diastereomerism and meso isomerism
and racemic modification. Configuration and conformation. Stereochemical descriptors: D, L; R,
S; E, Z; syn, anti, etc. Axial, planar and helical chirality. Steroprojections – Fischer, Sawhorse,
Newman and wedge projections and their interconversions. Absolute and relative configurations
and their determination; molecules with one, two or more chiral centres. Simple chemical
correlation of configurations with examples, quasiracemates. Stereochemistry and configurations
of allenes, spiranes, alkylidine cycloalkanes, adamantanes, catenanes, bbiphenyls
(atropisomerism), bridged biphenyls, ansa compounds and cyclophanes.
Unit 5: Stereochemistry 2
Topocity and prochirality: Topocity of ligands and faces and their nomenclature. Cram’s, and
Prelog’s. Stereoselectivty and stereospecificity and enatiomeric diastereomeric excess,
Asymmetric induction. Configuration, conformation and stability of cyclohexanes, cyclohexene
(mono and disubstituted), cyclohexanones, halocyclohexanones, decalins. Qualitative correlation
between conformation and reactivity, Stereochemistry of Compounds having P, N and S.

Book Suggested:
1. Carey, F.A. & Sundberg, R. J. Advanced Organic Chemistry, Parts A & B, Plenum: U.S.
(2007).
2. Eliel, E.L. Stereochemistry of Carbon Compounds Textbook Publishers (2003).
3. Finar, I. L. Organic Chemistry Vol. 1, Longman (1998).
4. Lowry, T. H. & Richardson, K.S. Mechanism and Theory in Organic Chemistry Addison –
Wesley Educational Publishers, Inc. (1981).
5. Nasipuri. D. N. Stereochemistry of Organic Compounds: Principles & Applications South
Asia Books (1994).
6. March, J. Advanced Organic Chemistry John Wiley & Sons (2004).
7. Kalsi, P.S. Stereochemistry: Conformation and Mechanism, 7th Edition New Age
International, Delhi (2008).
8. Sengupta.

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