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Indian Institute of Science Education and Research Bhopal

CHM 311: Organic Chemistry I (4)

Prerequisites: CHM 101, CHM 211

Learning Objectives:

This is a fundamental course where student initially can learn stereochemistry of organic molecules such as conformational analysis of cyclic and acyclic compounds. Further, dynamic stereochemistry and reactivity of simple molecules will be discussed. In the second part, various rearrangement (electrophillic, nucleophillic, sigmatropic, etc) reactions would be covered. In the third part of this course, the functional group inter-conversion based on oxidation and reduction protocols would be covered.

Course Contents:

Stereochemistry:

• Conformational analysis, conformation of acyclic, cyclic, fused and bridged systems
• Strain in cyclic and acyclic molecules including allylic strain (A1,2 and A1,3)
• Dynamic stereochemistry: Conformation and reactivity, Curtin-Hammett principle

Rearrangement Reactions:     

• Electrophilic (Beckmann, Hofmann, Lossen, Curtius, Wolff, Schmidt, Baeyer-Villiger, Pinacol-pinacolone, Wagner-Meerwein etc.), nucleophilic (benzilic acid, Favorskii), and radical rearrangements (Wittig, aza-Wittig)
• Sigmatropic rearrangements (Cope, aza-Cope, Oxy-Cope, Claisen, aza-Claisen, Eschenmoser-Claisen, vinyl cyclopropane-cyclopentene)
• Miscellaneous (Brook, Pummerer)

 Oxidations:                                                                 

• Oxidation of alcohols, ketones and aldehydes (transition metal oxidants, hypervalent iodine based, sulphur based, peroxide and peracid, etc.)
• Oxidation of C-C double bonds (Ozone, KMnO4, Pb(OAc)4, Dimethyldioxirane, OsO4, 2-sulfonyl oxaziridine etc.)
• Oxidation at unfunctionalized carbon

Reductions:                                         

• Reduction of carbonyl compounds (hydrogenation, reductions using group III, IV hydride donors, reductive deoxygenation), carbon-carbon multiple bonds (catalytic hydrogenation, diimide reduction) and other selected functional groups
• Dissolving metal reductions

Heterocyclic Chemistry:                                             

• General overview and nomenclature of heterocyclic compounds (structure of 3 to 7 membered saturated and 5,6 membered aromatic heterocycles)
• Synthesis and reactions of heterocyclic compounds (in brief)

Suggested Books:

• Clayden, J., Greeves, N., Warren, S., Wothers, S. Organic Chemistry, Oxford University Press, 2001.
• Eliel, E. L., Wilen, S. H., Doyle, M. P. Basic Organic Stereochemistry, John Wiley and Sons, 2001.
• Smith, M. B. and March, J. Advanced Organic Chemistry, Wiley Interscience, 2007.
• Carey, F. A, Sundberg, R. J. Advanced Organic Chemistry, Part A and B, Springer, 2007.
• Anslyn, E. V., Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, 2005.
• Hornback, J. M. Organic Chemistry, Cengage Learning, 2006.

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