Heterocyclic Chemistry

Paper Code: 
24CCHY512
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

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: 

Course

Learning Outcome

(at course level)

Learning and Teaching Strategies

Assessment Strategies

Course Code

Course

Title

 

24CCHY512

 

Organic Chemistry III: Heterocyclic Chemistry

(Theory)

 

 

 

CO95: Describe some of the important methods of preparation and properties of aliphatic and aromatic nitro and amino compounds mechanistically. Discuss the mechanism of diazotization and their applications.

CO96: Discuss the preparation and properties of some prescribed poly-nuclear hydrocarbons and their important derivatives.

CO97:Outline mechanisms for reactions involving heterocycles (five and six membered) as starting materials and propose syntheses of heterocycles from the major classes.

CO98: Explain the structure, preparation and properties of some fused ring heterocycles.

CO99: Classify different types of alkaloids, and terpenoids and discuss their chemistry & medicinal importance. 

CO100: 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 and 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: 
  1. Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  2. Organic Chemistry, Vol. I and II, Sixth Edition; I.L. Finar; Pearson Education, New Delhi, 2002.

 

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

e-Resources:

  1. https://www.egyankosh.ac.in/handle/123456789/15709 (Unit III and IV)
  2. http://www.chem.gla.ac.uk/staff/stephenc/teaching/Heterocycle Lectures2011_2C12.pdf (Unit III and IV)
  3. http://oms.bdu.ac.in/ec/admin/contents/1_16SCCCH8_2020051904202312.pdf (Unit V)

 

Academic Year: