Synthetic Strategies in Organic Chemistry

Paper Code: 
CHY- 421
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

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):

                                                                                                                                  

COURSE

Learning outcomes (at course level)

Learning and teaching strategies

Assessment Strategies

Paper Code

Paper Title

CHY  421

Strategies in Organic Synthesis

The students will be able to-

 

CO131-plan an organic synthesis using suitable reagents to understand a range of more sophisticated approaches to synthesis (building on the knowledge from previous years) that exploit the properties of other elements (particularly phosphorous, sulphur, silicon, boron, lithium, lanthanides and certain transition metals)

CO132-apply chemistry involving main group and transition metallic reagents to the synthesis of complex organic compounds.

CO133-justify the selection of one type of reagent and reaction conditions over another in terms of efficacy in relation to a particular synthetic problem.

CO134-analyze the environmental impacts of chemistry and discover the importance of Green Chemistry.

CO135-apply the green chemical sustainable tools for cleaner environment & energy.

 Interactive Lectures

 

Discussions

 

Tutorials

 

Quiz

 

Problem solving

 

Written test

 

Google Quiz

 

Assignment

 

Semester End Exam
 

 

12.00
Unit I: 
Oxidation Reactions
Metal-based and non-metal based oxidations of:
 
  1. alkenes to alcohols/carbonyls -hydroboration-oxidation,chiral boranes, Wacker oxidation,    SeO2/ selenium oxidants, chromium based oxidation.
  2. alkenes to epoxides (peroxides/per acids based):sharpless asymmetric epoxidation,        Jacobse  epoxidation, Shi epoxidation.
  3. alkenes to diols (manganese, osmium based): sharpless asymmetric dihydroxylation, Prevost reaction and Woodward modification.
  4. ketones to ester/lactones(Baeyer-Villiger), Corey-Kim oxidation, Dess-Martin oxidation,           Swern oxidation.
  5. alcohols to carbonyls (manganese, aluminium, hypervalent iodine and TEMPO based       reagents).              
 
10.00
Unit II: 
Reduction Reactions
  1. Catalytic hydrogenation (Homogeneous hydrogenation: Wilkinson, Noyori asymmetric     hydrogenation, stereo and enantioselective hydroboration.
  2. Metal based reductions using Li and Na in liquid ammonia, Birch reduction,Mc Murry, acyloin formation.
  3. Hydride transfer reagents.
  4. 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
  1. Metal  mediated  C- C and  C-X coupling reactions: Suzuki, Heck.  Stille, Sonogashira   cross coupling, Buchwald-Hartwig amination and Negishi, Kumada coupling reactions.     Umploung
  2. 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
  3. Multicomponent Reactions: Mannich. Biginelli, Hantzsch, Passerini. Ugi reaction.
  4. Ring Formation Reactions: Pausan-Khand reaction. Bergman cyclisation. Nazarov   cyclisation.
  5. Click Chemistry: Criteria for Click reaction, Sharpless azide cycloadditions.
  6. 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.

 

 

References: 
  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;KluwerAcademic/Plenum Publishers, New York, 2000-01.
  4. A Guide book to Mechanism in Organic Chemistry;SixthEdition;P. Sykes; Pearson Education, Delhi, 2011.
  5. Reaction Mechanism in Organic Chemistry;ThirdEdition;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;TataMcGraw 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: 
2019-2020
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