NITROGEN CONTAINING FUNCTIONAL GROUPS, NATURAL PRODUCTS AND DRUGS

Paper Code: 
CHY 412
Credits: 
3
Contact Hours: 
45.00
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-

CO101: describe some of the important methods of preparation and properties of aliphatic and aromatic nitro and amino compounds mechanistically.

CO102: classify different dyes on the basis of their applications, synthesize and correlate their structure and reactivity  

CO103: outline mechanisms for reactions involving heterocycles (five and six membered) as starting materials and propose syntheses of heterocycles from the major classes.

 CO104: classify different types of alkaloids, and terpenoids and discuss their chemistry & medicinal importance

CO105: describe the structure and medicinal importance of prescribed antipyretic, analgesics, antibiotics, antimalarials and sulpha drugs.
  • Class lectures
  • Tutorials
  • Group discussions
  • Use of models
  • Assertion and reasoning
  • Technology enabled learning
  • Peer learning

 
  • Oral and written examinations
  • Problem solving exercises
  • Assignments
  • Quiz
  • Efficient delivery using seminar presentations
  • Group activity
  • Multiple choice questions
  • Short answer type questions
  • Assertion and reasoning

 

 
 

 

9.00
Unit I: 
Nitrogen Containing Functional Groups

Preparation and important reactions of aliphatic and aromatic nitro compounds
Amines (aliphatic and aromatic)- effect of substituent and solvent on basicity, preparation and properties- Gabriel phthalimide synthesis, Hoffmann bromamide reaction, Carbylamine reaction, Mannich reaction, Hoffmann’s exhaustive methylation, Hofmann-elimination reaction, distinction between 1°, 2° and 3° amines with Hinsberg reagent and nitrous acid, amines as phase transfer catalyst.

 

9.00
Unit II: 
Synthetic Dyes

Diazonium Salts- preparation and their synthetic applications.
Colour and constitution (electronic concept), classification of dyes, chemistry and synthesis of methyl orange, congo red, malachite green, crystal violet, phenolphthalein, fluorescein, alizarin and indigo.

 

9.00
Unit III: 
Heterocyclic Compounds

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, indole (Fischer indole synthesis and Madelung synthesis), quinoline (Skraup synthesis, Friedlander’s synthesis, Knorr quinoline synthesis, Doebner-Miller synthesis) and isoquinoline (Bischler-Napieralski reaction, Pictet-Spengler reaction, Pomeranz-Fritsch reaction).

 

 

9.00
Unit IV: 
Alkaloids & Terpenoids

Alkaloids- natural occurrence, general structural features, isolation and their physiological action, Emde’s modification, structure elucidation and synthesis of nicotine, medicinal importance of nicotine, hygrine, quinine, morphine, cocaine and reserpine.
Terpenoids- occurrence, classification, isoprene rule, elucidation of structure and synthesis of citral and α- terpineol.

 

 

9.00
Unit V: 
Pharmaceutical Compounds: Structure and Importance

Mechanism of drug action (brief idea), classification, structure and therapeutic uses of-
Antipyretics- paracetamol (with synthesis)
Analgesics- ibuprofen (with synthesis), phenacetin, aspirin
Antimalarials- chloroquine (with synthesis)
Antibiotics- chloramphenicol (with synthesis)
Sulpha drugs (with synthesis)- sulpha pyrimidine, sulpha guanidine, sulphamethazine, sulpha pyridine.

 

Essential Readings: 
  • Organic Chemistry, Vol II, Sixth Edition; I. L. Finar; Pearson Education, New Delhi, 2016.
  • Heterocyclic Chemistry, Vol. II, First Edition; R. R. Gupta, M. Kumar; Springer (India) Pvt. Ltd., 2005.
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  • Medicinal Chemistry, Vol I, First Edition; A. Kar; New Age International (P) Ltd., New Delhi, 2020.

 

References: 

SUGGESTED READINGS

  • A Textbook of Synthetic Dyes, O.D. Tyagi, M. Yadav; Anmol Publications Pvt. Ltd, New Delhi, 2002.
  • Organic Chemistry, Twelfth Edition (Global Edition); T. W. Graham Solomons, C. B. Fryhle, S. A. Snyder; Wiley Publishers, United Kingdom, 2017.

e-RESOURCES

 

Academic Year: 
2022-2023
  • Printer-friendly version
  • PDF version