Synthetic Strategies in Organic Chemistry

Paper Code: 
24CHY426B
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

This course will enable the students to

gain advanced knowledge in synthetic organic and green chemistry so that the learner can suggest alternative reagents and reactions for performing desired organic transformations.

 

Course Outcomes: 

Course

Learning outcome

(at course level)

Learning and Teaching Strategies

Assessment Strategies

Course Code

Course

Title

 

24CHY426B

 

Synthetic Strategies in Organic Chemistry (Theory)

CO185:                 Plan an organic synthesis using suitable reagents to understand a range of more sophisticated approaches to synthesis (building on the knowledge from previous years).

CO186:  Apply reduction methods  involving main group and transition metal reagents for the synthesis of complex organic compounds.

CO187:   Predict the newer synthetic tools for the selection of one type of reagent and reaction conditions over another in terms of efficacy in relation to a particular synthetic problem.

CO188:   Solve the mechanistic problems in a facile manner using the prescribed organocatalysts.

CO189:Analyze the environmental impacts of chemistry and apply the green chemical tools, for cleaner environment and energy.

CO190:Contribute effectively in course-specific interaction.

Approach in teaching:

Interactive lectures, tutorials, group discussions and e-learning.

 

Learning activities for the students:

Peer learning, e- learning, problem solving through tutorials and group discussions.

 

 

Written examinations,

Assignments, Quiz

 

 

14.00
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, Jacob-          Katsuki 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.
  5. Alcohols to carbonyls- Corey-Kim oxidation, Dess-Martin oxidation, Swern oxidation.        Manganese, aluminium, hypervalent iodine and TEMPO based reagents.

 

 

12.00
Unit II: 
Reduction Reactions
  1. Catalytic hydrogenation (Homogeneous hydrogenation: Wilkinson, Noyori asymmetric    hydrogenation, stereo and enantioselective hydroboration.
  2. Metal based reductions: 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,         Clemmensen and Wolff-Kishner reduction.

 

13.00
Unit III: 
Newer Synthetic Reactions-I
  1. Metal mediated C- C and C-X coupling reactions: Suzuki, Heck. Stille, Sonogashira cross   coupling, Buchwald-Hartwig amination and Negishi, Kumada coupling reactions. Umpolung.
  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.

 

 

10.00
Unit IV: 
Newer Synthetic Reactions-II
  1. Ring Formation Reactions: Pausan-Khand reaction, Bergman cyclisation, Nazarov     cyclisation.
  2. Click Chemistry: Criteria for Click reaction, Sharpless azide cycloadditions.
  3. 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.

 

11.00
Unit V: 
Organocatalysis

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.

 

Essential Readings: 
  1. Organic Chemistry, Second edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2012.
  2. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.

 

 

References: 
  1. Advanced Organic Chemistry Part A & B, Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
  2. A Guidebook to Mechanism in Organic Chemistry, Sixth Edition; P. Sykes; Pearson Education, Delhi, 2011.
  3. Reaction Mechanism in Organic Chemistry, Third Edition; S. M. Mukherjee and S. Singh; Macmillan India Ltd., New Delhi, 2003.
  4. Mechanism and Theory in Organic Chemistry; Third Edition; T.H. Lowry; Addison– Wesley Publishing Company, 1999.
  5. Organic Chemistry; Fifth Edition; S.H. Pine; Tata McGraw Hill Publishing Company,2007.
  6. Modern Methods of Organic Synthesis; Fourth Edition; W. Carruthers; Cambridge Univ. Press, UK, 2005.
  7. Principles of Asymmetric Synthesis; Second Edition; R. Gawley and J. Aube; New York: Pergamon Press, 2012.

 

e-Resources:

  1. https://hwpi.harvard.edu/files/myers/files/6-oxidation.pdf (Oxidation Reactions)
  2. https://www.vanderbilt.edu/AnS/Chemistry/Rizzo/chem223/Oxidations.pdf (Oxidation Reactions)
  3. https://hwpi.harvard.edu/files/myers/files/5-reduction.pdf (Reduction Reactions)
  4. https://nptel.ac.in/courses/104103067 (Organocatalysis)
  5. https://application.wiley-vch.de/books/sample/352730715X_c01.pdf (Green Chemistry)

 

Academic Year: 
2024-2025
  • Printer-friendly version
  • PDF version