Synthetic Strategies in Organic Chemistry

Paper Code: 
CHY 421
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
12.00
Unit I: 
Oxidation Reactions

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,           Jacobse  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), Corey-Kim oxidation, Dess-Martin oxidation, Swern oxidation.

(e)        alcohols to carbonyls (manganese, aluminium, hypervalent iodine and TEMPO based       reagents). 

 

10.00
Unit II: 
Reduction Reactions

(a) Catalytic hydrogenation (Homogeneous hydrogenation: Wilkinson, Noyori asymmetric     hydrogenation, stereo and enantioselective hydroboration.

(b)        Metal based reductions using 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.

 

16.00
Unit III: 
Newer Synthetic Reactions

(a) Metal  mediated  C- C and  C-X coupling reactions: Suzuki, Heck.  Stille, Sonogashira      cross coupling, Buchwald-Hartwig amination and Negishi, Kumada coupling reactions.           Umploung

(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,

 

12.00
Unit IV: 
Organocatalysis

Introduction to organocatalysis, phosphorus based catalysts eg., phosphagenes, triphenyl phosphenes, phosphonates etc., amidines, guanidines. Thiourea based catalysis . Lewis base catalysis, iminium catalysis, enamine catalysis. Jacobson catalyst.

Carbenes as organocatalysts, N-hetrocyclic carbenes (N-HCs) - synthesis, umpolung, transesterification reactions, homo and cross benzoin type coupling, Stetter reaction,

10.00
Unit V: 
Green Chemistry

Green Chemistry & sustainability , twelve principles of green chemistry, atom economy, E-factor, carbon foot-print, carbon credit and carbon trading.

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 , C 1 chemistry.

Green catalysts: Types , advantages and disadvantages ,applications in organic synthesis.

 

Essential Readings: 
  1. Organic Chemistry; First Edition; J. Clayden, N. Greeves, S. Warren and P. Wothers; Oxford University Press, 2009.
  2. Advanced Organic Chemistry: Reactions, Mechanism and Structure; Seventh Edition; M.B. Smith & J. March, USA: Wilet Publishing Inc., 2013.
  3. Advanced Organic Chemistry; Part A and Part B; Fourth and Fifth Edition; F.A. Carey and R. J. Sundberg;  Kluwer Academic/Plenum Publishers, New York, 2000-01.
  4. A Guide book to Mechanism in Organic Chemistry; Sixth Edition; P. Sykes; Pearson Education, Delhi, 2011.
  5. Reaction Mechanism in Organic Chemistry; Third Edition; S. M. Mukherjee and S. Singh; Macmillan India Ltd., New Delhi, 2003.
  6. Mechanism and Theory in Organic Chemistry; Third Edition; T.H. Lowry; Addison– Wesley Publishing Company, 1999.
  7. Organic Chemistry; Fifth Edition; S.H. Pine; Tata McGraw Hill Publishing Company, 2007.
  8.       Modern Methods of Organic Synthesis; Fourth Edition; W. Carruther; Cambridge             University Press, 1971.
  9. Principles of Asymmetric Synthesis; Second Edition; R. Gawley and J. Aube; New York:             Pergamon Press, 2012.
Academic Year: 
2018-2019
  • Printer-friendly version
  • PDF version