Selected Topics in Organic Chemistry

Paper Code: 
CHY 144B
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
12.00
Unit I: 
Stereochemistry –I

Configuration, chirality and asymmetry, molecules with one, two or more chiral centres, configuration nomenclature, Prelog’s rule, D/L and R/S types of racemates and methods of resolution.
Prochirality, topicity of ligands and faces and their nomenclature, stereogenicity, pseudoasymmetry, planar chirality, axial chirality, optical purity, chirogenicity, stereogenic and prochiral centres.
Optical activity in the absence of chiral carbons, biphenyls, allenes, alkyldienes, cycloalkyldienes, spiranes, ansa compounds, adamantanes, and cyclophanes, chirality due to helical shape (P & M), chirality in the compounds containing N, S and P.

 

12.00
Unit II: 
Stereochemistry – II

Conformation and stability of cyclohexanes (mono-, di-, and trisubstituted), cyclohexenes, cyclohexanones, halocyclohexanones, decalins, decalols and decalones, effect of conformation on reactivity, strain in cycloalkanes.
Chiral synthesis, stereoselective and stereospecific synthesis, Felkin-anh rule, CD, ORD, octant rule, Cotton effect and their application in determination of absolute and relative configuration and conformation, the axial haloketone rule.
Chiral auxiliary and chiral pool.

 

12.00
Unit III: 
Disconnection approach of synthesis

An introduction to synthons and synthetic equivalents, disconnection approach, functional group inter-conversions, the importance of the order of events in organic synthesis, chemoselectivity, reversal of polarity, one group C-X and two group C-X and C-C disconnections, Diels- Alder reaction, 1, 3 and 1, 5difunctionalised compounds, a,ß-unsaturated carbony1 compounds, cyclisation reactions, amine synthesis; Principle of protection of alcohol, amine, carbonyl and carboxyl groups. 

 

12.00
Unit IV: 
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. 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.
  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 V: 
Green Chemistry

Basic principles of green chemistry, applications of non-conventional techniques in organic synthesis and natural products (ultrasonic, microwave and electro synthesis). Solid state synthesis and synthesis under solvent free conditions. Use of ionic solvents, biocatalysts, nanoparticles etc.

 

Essential Readings: 
  • Stereochemistry: Conformation and Mechanism, Tenth Edition; P.S. Kalsi; New Age International Publishers Pvt. Ltd, New Delhi, 2019.
  • Stereochemistry of Organic Compounds, Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  • Designing Organic Synthesis; First Edition; S. Warren; John Wiley and Sons, Great Britain, 2002.
  • Organic Chemistry, Second edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2012.
  • Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
  • Green Chemistry: Introductory Text, Third Edition; M. Lancaster; Royal Society of Chemistry (London), 2016.

 

Academic Year: