National Institute of Technology Rourkela

राष्ट्रीय प्रौद्योगिकी संस्थान राउरकेला

ଜାତୀୟ ପ୍ରଯୁକ୍ତି ପ୍ରତିଷ୍ଠାନ ରାଉରକେଲା

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Syllabus

Course Details

Subject {L-T-P / C} : CY4102 : Reagents and Rearrangements in Organic Synthesis { 3-1-0 / 4}

Subject Nature : Theory

Coordinator : Niranjan Panda

Syllabus

Module 1 :

Reactive intermediates and name reactions: Generation, structure, stability and reactions involving the intermediates: Carbocation (Pinacol-Pinacolone Rearrangement, Wagner-Meerwein Rearrangement, Demjanov reaction, Favorski Rearrangement, Fries Rearrangement, Benzil-Benzilic Acid Rearrangement), carbanion (Alkylation, Aldol condensation (asymmetric reaction), Robbinson annulation, Claisen condensation, Dieckmann condensation Reaction, Perkin Reaction, Stobbe Condensation Reaction, Moritas-Baylis-Hilmann reaction, Bamford-Steven, Shapiro reaction), Free radicals (Allylic halogenations, acyloin condensation, McMurry coupling, Hunsdiecker reaction, Bouveault-Blanc reduction), carbenes (Wolff Rearrangement, Reimer-Tiemann), nitrenes (Hofmann, Beckmann, Curtius, Schmidt, Lossen Rearrangement), arynes, phosphorous ylides (Wittig Reaction), sulfur ylides.
Oxidizing reagents: Chromium reagents, manganese reagents, Ruthenium tetroxide, TPAP, Lead tetraacetate, Osmium tetroxide, Hypervalent Iodine reagents [Dess-Martin periodinane (DMP), o-iodoxybenzoicacid (IBX)], Cerric ammonium nitrate, DDQ, Selenium dioxide, DMSO based oxidizing reagents, Aluminiumalkoxides (Oppenauer Oxidation), peroxyacids.
Reducing reagents: Heterogeneous catalytic hydrogenation, Homogeneous Catalytic hydrogenation (Wilkinson’s Catalyst), Dissolving metal reduction (Clemmesen Reduction Reaction, Birch Reduction)Reduction with hydride-transfer reagents (Aluminiumalkoxides, Lithium aluminium hydride, sodium borohydride, DIBAL-H, Tinhydrides, Silanes, diimide, Borane and derivatives.

Course Objective

1 .

To make students familiar with the Generation of different reactive intermediates for organic synthesis

2 .

To understand the organic reactions involving reactive intermediates

3 .

To gain knowledge on reagents that are used in organic synthesis

4 .

To gain confidence in deriving the mechanism of an organic transformation.

Course Outcome

1 .

1)This course will give an understanding of reactive intermediates and their involvement in organic synthesis.
2)This course will give a detailed understanding of the reactivity and applications of important reagents used in organic synthesis.
3) It will provide knowledge on principles and mechanisms of different kinds of rearrangements in organic chemistry.
4) Helps students to derive synthetic strategies for simple organic molecules.
5) It provides an understanding of the oxidizing and reducing agents and their use in organic synthesis

Essential Reading

1 .

J. Clayden, N. Greeves, and S. warren, Organic Chemistry, Oxford University Press , Second edition, 2012.

2 .

R. K. Kar, Name Reactions and Rearrangements in Organic Chemistry, New India Book Agency

Supplementary Reading

1 .

W. carruthers, I. Coldham, Modern methods of organic synthesis, Cambridge University press , Fourth edition, 2004.

2 .

4. A. R. Parikh, H. Parikh and K. Parikh, Name reactions in Organic Synthesis, Foundation Books