Course

Unit I

Synthetic Strategies
Synthetic strategies: Functional group inter-conversion conversion of one functional group to other. Nitrogen, oxygen, sulphur protection and deprotection utilization of protection groups in organic synthesis. Retro synthetic analysis, functional group equivalents, use of retrosynthesis in organic synthesis. Reversal of reactivity (Umpolung), Introduction to combinatorial chemistry. Application of phase transfer catalysts.

Unit II

Oxidation and Reduction:PCC, DDQ, DMSO, Dess-Martin Reagent, TEMPO, osmium tetroxide, ruthenium tetroxide, selenium dioxide, peracids, hydrogen peroxide, singlet oxygen, aluminum isopropoxide, periodic acid, lead tetraacetate. Swern, Jones, Oppeneur oxidation, Woodward and Prevost hydroxylation, Sharpless asymmetric epoxidation, catalytic hydrogenations (heterogeneous and homogeneous), Clemmenson, Wolff Kishner, Rosenmund and MPVreductions, metal hydrides as reagents (aluminium/boron hydrides and hydroboration reaction), Birch reduction, Borche Reduction, hydrazine and diimide reduction.

Unit III

Organometallic Reagents
Preparation, properties and reactions of organolithium, organosilicon, organozinc (Reformatsky reaction) and organomagnesium reagents (Barbier and Grignard), organocadmium, organomercury reagents based organometallic reactions involving C-C bond formation. Selected functional group transformations in organic synthesis. Preparation and reactions of organocopper, organopalladium,- Wacker process Heck reaction, cross coupling, carbonylation reaction, organonickel, organocobalt and organorhodium reagents olefin metathesis reaction. Reactions and applications of organoboron, organosilicon and organotin compounds.

Unit IV

C-C Bond Formation
C-C bond formation aldol, Arndt-Eistert, Bardhan-Sengupta, Baker-Venkataraman,Barbier, Baylis-Hillman, Benzoin, Heck, Fukuyama, Dieckmann, FriedelCrafts, Michael, Perkin, Claisen, Robinson annulations, Vilsmeier, Wittig, Knoevenagel, Michael additions.

Unit V

C-N, C-O Bond Formations
C-O bond formation Barton, Fischer esterification, Prins, Darzen, Baeyer-Villiger, Mitsunobu, Williamsons ether synthesis, Ullman Coupling with Boronic Acids.C-N bond formation Mannich, Fukuyama, Mitsunobu, Ritter, Gabriel Synthesis, Ugi, Doebner Reaction, Buchwald-Hartwig, Stork-enamine, formation of azides and hydrazines, formation of amides and peptides, coupling reactions.

• CO1: Analyze the mechanisms involved in different types of organic processes
• CO2: Evaluate the chemical and physical properties of oxygen and nitrogen containing organic compounds
• CO3: Apply the knowledge of basic reaction mechanisms to synthesize wide range of important aromatic and aliphatic compounds including alcohols, phenol, ethers, etc.
• CO4: Elucidate the structure and reactivity of various organic compounds containing carbonyl functional groups
• CO5: Design synthesis of various common organic compounds.

Textbooks

1. Modern Organic Synthesis, Dale L. Boger, The Scripps Research Institute, Rush Press, San Diego, California, 2001
2. Francis A. Carey and Richard J. Sundberg, “Advanced Organic Chemistry – Part B: Reactions and Synthesis”, 5^th Edition, Springer, 2008.
3. O.C. Norman and J. M. Coxon, “Principles of organic synthesis”, CRC press, 2014

References

1. Stuart Warren, Designing Organic Synthesis: A programmed introduction to the synthon approach, JOHN WILEY & SONS, 2^ndedition, 2008
2. Name Reactions: A collection of detailed Mechanisms and synthetic applications, Jie Jack Li, Springer, fourth edition (expanded edition), 2009.
3. Michael B Smith, “March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure”, 7^th edition, Wiley (2015).
4. Francis A. Carey and Richard J. Sundberg, “Advanced Organic Chemistry-Part A: Structure and Mechanisms”, 5^th Edition, Springer, 2008