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Strategies in Organic Synthesis
Course Objectives :
The aim of the course is to give advanced knowledge in synthetic organic chemistry so that the learner can suggest alternative reagents and reactions for performing desired organic transformations. It is also aimed at making students aware of the basic principles and applications of green chemistry so that they acquire the competence to think, design and develop sustainable chemistry.
Course Outcomes (COs):
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COURSE |
Learning outcomes (at course level) |
Learning and teaching strategies |
Assessment Strategies |
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Paper Code |
Paper Title |
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CHY 421 |
Strategies in Organic Synthesis |
The students will be able to-
CO131- appraise the metal and non-metal-based oxidation and reduction reactions from the mechanistic, stereochemistry and regiochemistry point of view. CO132- appraise the newly reported organic reactions along with the mechanisms involved in the formation of C-C, C-X, C=C bonds. CO133-demonstrate the use of organocatalysts specifically, Covalent, Noncovalent and Phosphorus containing organocatalysts in the synthesis of a diverse range of organic compounds CO134-justify the use of a specific organic reagent and catalyst in a particular reaction via the mechanism of the reaction CO135- analyze the environmental impacts of chemistry and highlight the use and significance of 12 basic principles of Green Chemistry and hypothesise novel organic compounds using the newer greener sustainable technologies and methods for cleaner environment & energy.
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Interactive Lectures
Discussions
Tutorials
Quiz
Problem solving
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Written test
Google Quiz
Assignment
Semester End Exam |
Metal-based and non-metal based oxidations of:
(a) Alkenes to alcohols/carbonyls-hydroboration-oxidation, chiral boranes, Wacker oxidation, SeO2/ selenium oxidants, chromium based oxidation.
(b) Alkenes to epoxides (peroxides/per acids based)-Sharpless asymmetric epoxidation, Jacob-Katsuki epoxidation, Shi epoxidation.
(c) Alkenes to diols ( manganese, osmium based)- Sharpless asymmetric dihydroxylation, Prevost reaction and Woodward modification.
(d) Ketones to ester/lactones- Baeyer- Villiger.
(e) Alcohols to carbonyls- Corey-Kim oxidation, Dess-Martin oxidation, Swern oxidation.Manganese, aluminium, hypervalent iodine and TEMPO based reagents.
(a) Catalytic hydrogenation (Homogeneous hydrogenation: Wilkinson, Noyori asymmetric hydrogenation, stereo and enantioselective hydroboration.
(b) Metal based reductions : Li and Na in liquid ammonia, Birch reduction, Mc Murry, acyloin formation
(c) Hydride transfer reagents.
(d) NaBH4, triacetoxyborohydride, L-selectride, K-selectride, Luche reduction; LiAlH4, DIBAL-H, and Red-Al, trialkylsilanes and trialkylstannane, Meerwein-Pondorff-Verley reduction. Clemmenson and Wolff-Kishner reduction.
(a) Metal mediated C- C and C-X coupling reactions: Suzuki, Heck. Stille, Sonogashira cross coupling, Buchwald-Hartwig amination and Negishi, Kumada coupling reactions. Umpolung.
(b) C=C Formation Reactions: Wittig reactions and its modifications, Shapiro, Bamford-Stevens. Julia-Lythgoe olefination and Peterson’s stereoselective olefination, phosphorus, sulphur and nitrogen ylides, Stork-enamine reaction.
(c) Multicomponent Reactions: Mannich, Biginelli, Hantzsch, Passerini. Ugi reaction.
(d) Ring Formation Reactions: Pausan-Khand reaction, Bergman cyclisation,Nazarov cyclisation.
(e) Click Chemistry: Criteria for Click reaction, Sharpless azide cycloadditions.
(f) Olefin metathesis: Shrock’s, Grubb’s 1st and 2nd generation catalyst. Grubb-Hoveyda catalyst. Olefin cross metathesis (OCM), ring closing metathesis (RCM), ring opening metathesis (ROM) and applications.
Definition, generic modes, classification.
Covalent organocatalysis: Secondary amines via enamine, imine, imim ion, Amidines, guanidines , Lewis base catalysis, Nitrogen Heterocyclic Carbenes (NHC), synthesis, structure, catalysis-homo-and cross-benzoin condensation, Stetter reaction, hydrosilylation of styrenes, transesterification.
Noncovalent organocatalysis: Hydrogen bonding catalysis, thiourea based catalysts, Diols: TADDOL.
Phosphorus containing organocatalysts: Triphenylphosphine, Binol-derived phosphoric acids, cyclic diphosphazanes, phosphonates.
Green Chemistry & sustainability, twelve principles of green chemistry, atom economy, E-factor.
Green chemistry tools:
Solvents: Types based on hazards, applications, green solvents-supercritical fluids, ionic liquids, water, solvent free solid phase reaction.
Alternative energy sources: Ultrasound, microwave, reactions at high pressure in constrained media.
Renewable sources, C1 chemistry.
Green catalysts: Types, advantages and disadvantages, applications in organic synthesis.
- Organic Chemistry; First Edition; J. Clayden, N. Greeves, S. Warren and P. Wothers; Oxford University Press, 2009.
- Advanced Organic Chemistry: Reactions, Mechanisms and Structure; Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
- Advanced Organic Chemistry Part A & B; Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
- A Guidebook to Mechanism in Organic Chemistry;SixthEdition;P. Sykes; Pearson Education, Delhi, 2011.
- Reaction Mechanism in Organic Chemistry;ThirdEdition;S. M. Mukherjee and S. Singh; Macmillan India Ltd., New Delhi, 2003.
- Mechanism and Theory in Organic Chemistry; Third Edition; T.H. Lowry; Addison– Wesley Publishing Company, 1999.
- Organic Chemistry; Fifth Edition; S.H. Pine;TataMcGraw Hill Publishing Company,2007.
- Modern Methods of Organic Synthesis; Fourth Edition; W. Carruthers; Cambridge Univ. Press, UK, 2005.
- Principles of Asymmetric Synthesis; Second Edition; R. Gawley and J. Aube; New York: Pergamon Press, 2012.
