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Alder reaction, regioselectivity, periselectivity, torque selectivity, site selectivity and effect of
substituents in Diels-Alder reactions. Other Cycloaddition Reactions- [4+6] Cycloadditions,
Allene Cycloadditions
UNIT-II Pericyclic Reactions-II (11 Hours)

Electrocyclic reactions – controtatory and disrotatory motions, 4n, 4n+2, allyl systems secondary
effects. Electrocyclic rearrangement of cyclobutenes and 1,3 cyclohexadienes. Sigmatropic
Rearrangements: H-shifts and C-shifts, supra and antarafacial migrations, retention and inversion
of configurations, detailed treatment of Claisen and Cope rearrangements, fluxional tautomerism,
aza-cope rearrangements, introductions to Ene reactions. Formation of Vitamin D from 7-
dehydrocholesterol, synthesis of citral using pericyclic reaction, conversion of Endiandric acid E
to Endiandric acid A.

UNIT-III Asymmetric synthesis (12 Hours)
Asymmetric synthesis and its need. Basis, principles and strategiesof asymmetric synthesis,
Sources of chiral compounds and methods (I-IV generations) of asymmetric synthesis,
Enantiomeric excess, Analytical methods for enantiomeric excess determination, Asymmetric
synthesis using chiral starting materials: addition to carbonyl compounds (face blocking/
diastereofacial bias, chiral sulfoxides, organometallics, chiral amplification), α-substitution using
chiral enolatesand chiral auxiliaries (SAMP, RAMP, SULTAM, EVANS, MASAMUNE).
UNIT-IV Asymmetric synthesis-II (11 Hours)

Enantioselective and diastereoslective aldol reactions, Asymmetric addition to C-C double bond:
Asymmetric hydrogenation, Enantioselective epoxidation, Enantioselective hydroxylation,
Asymmetric Diels-Alder reaction (use of chiral dienes and dienophiles), Asymmetric
hydroboration of alkenes, Asymmetric enzymatic transformations, oxidation, reduction and
hydrolysis.

PRACTICAL (30 Hours)

1. Qualitative Analysis: Separation, purification, and identification of binary mixture of
organic compounds, TLC, column chromatography and IR spectroscopy.
2. Organic Synthesis: Sandmeyer reaction: p-chlorotoluene from p-toluidine. Acetoacetic ester
condensation: Synthesis of ethyl-n-butylacetoacetate by A.E.E
Condensation. Preparation of iodoform from acetone (Haloform reaction).
Preparation of polystyrene, anthranilic acid, fluorosceine-eosin, and methyl orange

SUGGUESTED READINGS:

1. Fleming, I., Pericyclic Reactions, Pubs: Oxford Science Publications (2015).
2. Sankararaman, S. Pericyclic reactions a textbook: reactions, applications and theory, Pubs:
Wiley India, New Delhi (2016).
3. Gill, G.B.; Willis, M.R. Pericyclic Reactions, Pubs: London, Chapman & Hall. (1974).
4. Morrison J. D. (eds) Asymmetric Synthesis, Vol. 1 to 5, Pubs: Academic Press.(1992).
5. Aitken R.A. and Kilenyi S.N., Asymmetric Synthesis, Pubs: Academic Press. (1994).
6. Proctor Garry, Asymmetric Synthesis, Pubs: Academic Press (1996)

Chem.423 Surfaces and Macromolecules 3+1

LEARNING OBJECTIVES:

Objectives of this course are:
 To teach the fundamental concepts of surface chemistry and their applications.

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