ORGANIC CHEMISTRY III: HETEROCYCLIC CHEMISTRY

Paper Code: 
C-CHY512
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

Course Objective(s):

This course will enable the students to-

develop an insight on presence of nitrogen in functional groups or as a heteroatom in organic compounds   and their applications in various avenues of our day-to-day life.

 

Course Outcomes(COs):

Course Outcomes

Teaching Learning

Strategies

Assessment

Strategies

On completion of this course, the students will be able to-

CO70: describe some of the important methods of preparation and properties of aliphatic and aromatic nitro and amino compounds mechanistically.

CO71: discuss the mechanism of diazotization and their applications.

CO72:outline mechanisms for reactions involving heterocycles (five and six membered) as starting materials and propose syntheses of heterocycles from the major classes.

CO73: classify different types of alkaloids, and terpenoids and discuss their chemistry & medicinal importance.

CO74: describe the structure and reactions of polynuclear hydrocarbons and their derivatives.
  • Interactive lectures
  • Digital learning
  • Tutorials
  • Problem solving sessions
  • Oral and written examinations
  • Assignments
  • Quiz

 

12.00
Unit I: 
Nitrogen Containing Functional Groups

Preparation and important reactions of nitro and nitro compounds, nitriles and isonitriles. Amines: effect of substituent and solvent on basicity, preparation and properties: Gabriel phthalimide synthesis, Carbylamine reaction, Mannich reaction, Hoffmann’s exhaustive methylation, Hofmann-elimination reaction, distinction between 1°, 2° and 3° amines with Hinsberg reagent and nitrous acid.

Diazonium salts: preparation and their synthetic applications.

12.00
Unit II: 
Polynuclear Hydrocarbons

Structure and reactions of naphthalene, phenanthrene and anthracene, preparation, structure elucidation and important derivatives of naphthalene and anthracene.

12.00
Unit III: 
Heterocyclic Compounds I

Classification and nomenclature, structure, aromaticity in 5-numbered and 6-membered rings containing one heteroatom, synthesis, reactions and mechanism of substitution reactions of: furan, pyrrole (Paal-Knorr synthesis, Knorr pyrrole synthesis, Hantzsch synthesis), thiophene, pyridine (Hantzsch synthesis), pyrimidine.

12.00
Unit IV: 
Heterocyclic Compounds II

Structure elucidation of indole, Fischer indole synthesis and Madelung synthesis, structure elucidation of quinoline and isoquinoline, Skraup synthesis, Friedlander’s synthesis, Knorr synthesis, Doebner-Miller synthesis, Bischler-Napieralski reaction, Pictet-Spengler reaction, Pomeranz-Fritsch reaction, derivatives of furan: furfural and furoic acid.

12.00
Unit V: 
Alkaloids and Terpenes

Alkaloids: Natural occurrence, general structural features, isolation and their physiological action, Hoffmann’s exhaustive methylation, Emde’s modification, structure elucidation and synthesis of hygrine and nicotine,medicinal importance of nicotine, hygrine, quinine, morphine, cocaine, and reserpine.

Terpenes: Occurrence, classification, isoprene rule, elucidation of stucture and synthesis of citral, neral and α-terpineol.

Essential Readings: 
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  • Organic Chemistry, Vol. I and II, Sixth Edition; I.L. Finar; Pearson Education, New Delhi, 2002.

 

References: 

SUGGESTED READINGS

  • Organic Chemistry, Second Edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, USA, 2014.
  • Organic Chemistry, Fourth Edition (Indian Edition); G. Marc Loudon, J. Parise; WH Freeman, Oxford University Press, New Delhi, 2008.
  • Introduction to the Chemistry of Heterocyclic compounds;Acheson, R.M. John Welly & Sons, 2008.

e-RESOURCES

 

Academic Year: 
2023-2024
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