Advanced Course in Organic Chemistry

Paper Code: 
CHY 144 A
Credits: 
4
Contact Hours: 
60.00
Unit I: 
Stereochemistry I

Prerequisite: Basic concepts of stereochemistry, naming absolute configuration, prochirality,  enantiotopic and diastereotopic faces.

Introduction, stereospecific and regiospecific synthesis- Cram’s rule, chiral auxiliary, asymmetric induction, principles & examples of asymmetric synthesis (Michael addition, Diels-Alder reaction, epoxidation, reductions and hydroboration)

Concept of dynamic enantiomerism. Role of enzymes in chiral synthesis.

 

12.00
Unit II: 
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, carbony1 and carboxy1 groups. 

 

12.00
Unit III: 
Reagents and Reactions

Application of the following reagents with specific examples.

Organoboron  reagents (IBBN, CATB, IpC2BH, PINB). Organosilicon compounds, Triflates. Trimethylsilyl iodide, Baker’s yeast. Hypervalent iodine, Phase transfer catalysts, Lithium dimethycuprate, Lithium disopropylamide (LDA), dicyclohexy1 carbodiimide (DCC) 1,3-dithiane, DDQ, Heck, Vilsmayer, Mukaiyama and McMurray reaction and Suzuki and Sonogashira coupling.

12.00
Unit IV: 
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.

 

12.00
Unit V: 
Spectroscopic Techniques

UV: Visible molecular absorption spectrometry (instrumentation and application).

NMR Spectroscopy: Theory and applications of 1H and 13C  NMR spectroscopy.

Mass & IR Spectroscopy: Theory and applications.

Structural elucidation by UV, IR, NMR & Mass Spectra.

 

References: 
  1. Designing Organic Synthesis; First Edition; S. Warren; John Wiley and Sons, Great Britain, 2002.
  2. Advanced Organic Chemistry: Reactions, Mechanisms and Structure; Fourth Edition; Jerry March; John Wiley and Sons Asia Private Limited, New Delhi, 2007
  3. Spectral Analysis of Organic Compounds; Creswell and Campbell; Longman.
  4. Spectrometric Identification of Organic Compounds, Sixth Edition; R.M. Silverstein and F.X. Webster; John Wiley and Sons, Inc., Singapore, 1991.
Academic Year: 
2018-2019
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