Heterocyclic Chemistry

Teacher

Dr. Rosy Mallik

Category

Core Courses

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Course Name : Heterocyclic Chemistry

Code(Credit) : CUTM1477 (3-2-1)

Course Objectives

  • To introduce students to Nitrogen containing functional groups and their application in organic conversions and related mechanisms.
  • Students are also expected to learn about structure, synthesis, reactivity of important heterocyclic compounds and polycyclic aromatic hydrocarbons.
  • To familiarize students about different classes of N-based naturally occurring important alkaloid and terpenoid compounds, their structures, synthesis and reactivity.

Course Outcomes

  • COs Course outcomes Mapping COs with POs (High-3, Medium-2, Low-1)
    CO1 Able to gain knowledge in understanding the properties and synthesis of heterocyclic compounds and basic knowledge in bio-organic chemistry PO1(3)
    CO3 Able to enhance the ability to understand the organic chemistry and it will help in trouble shooting of organic reaction PO4(2), PO3(1)
    CO4 Able to get skill on extraction, purification and separation techniques and can be applied to organic synthesis. PO4(3)

Course Syllabus

Module-I (5 Hrs.)

Nitrogen Containing Functional Groups:Nitro compounds, nitriles and isonitriles
1.1 Structure and Preparation of nitroalkanes and nitroarenes
1.2 Properties and reactions of nitroalkanes
1.3 Properties and reactions of nitroarenes
1.4 Structure, Preparation and properties of nitriles and isonitriles

Assignment 1/Flip class: Important Nitro aromatic compounds and their uses

Module-II (8 Hrs.)

Nitrogen Containing Functional Groups:Amines
2.1 Preparation of primary amines: Reduction of nitro compounds, Hofmann ammonolysis, Hofmann degradation, Gabriel phthalimide synthesis.
2.2 Preparation of secondary and tertiary amines: Aminolysis of alkyl halides, Reductive amination of aldehydes and ketones, Ullmann reaction
2.3 Properties of amines, Basicity, Effect of substituent and solvent on basicity.
2.4 Important reactions of amines: Alkylation, acylation, Carbylamine reaction
2.5 Important reactions of amines: Mannich reaction, Hoffmann’s exhaustive methylation, Hofmann-elimination reaction
2.6 Diazonium Salts: Structure, Preparation and reactions/applications

Assignment 2/Flip class:Electrophilic substitution reactions of aryl amines

Assignment 3/Flip class:Distinction between 1°, 2° and 3°amines with Hinsberg reagent and nitrous acid.

Laboratory Practices (Module I and II): (13.30 hrs.)

1. Detection of extra elements (Nitrogen)

2. Detection of extra elements (Sulphur)

3. Detection of extra elements (Halogens)

4. Functional group test for: Nitro groups
5. Functional group test for: Amine groups
6. Functional group test for: Amide groups

Module-III (8 Hrs.)
Five membered Heterocyclic Compounds containing one heteroatom:
3.1 Classification, nomenclature and structure of pyrrole, furan and thiophene (5-numbered) and pyridine (6-membered)
3.2 Molecular orbital pictures and aromaticity in of pyrrole, furan and thiophene and pyridine
3.3 Synthesis, reactions and mechanism of substitution reactions of: Furan
3.4 Synthesis of Pyrrole: Knorr pyrrole synthesis, Paal-Knorr synthesis, Hantzsch synthesis.
3.5 Reactions and mechanism of substitution reactions of Pyrrole
3.6 Derivatives of furan: Furfural and furoic acid.

Assignment 4/Flip class:Synthesis and Properties of thiophene

Assignment 5/Flip class:Acidic and basic character of Pyrrole, Furan and Thiophene

Module-IV (6 Hrs.)
Six membered and condensed Heterocyclic Compounds:
4.1 Structure, synthesis and properties of Pyridine (Hantzsch synthesis), Pyrimidine
4.2 Structure elucidation of indole, Fischer indole synthesis and Madelung synthesis)
4.3 Structure elucidation of quinoline and isoquinoline
4.4 Skraup synthesis, Friedlander’s synthesis

Assignment 6/Flip class: Knorr quinoline synthesis, Doebner- Miller synthesis

Assignment 7/Flip class:Bischler-Napieralski reaction, Pictet-Spengler reaction, Pomeranz-Fritsch Reaction.

Module-V (5 Hrs.)
Polynuclear Hydrocarbons:
5.1 Preparation and structure elucidation of naphthalene
5.2 Reactions of naphthalene
5.3 Important derivatives of naphthalene
5.4 Preparation, structure elucidation and important derivatives of anthracene.

Assignment 8/Flip class:Preparation, structure elucidation and properties of phenanthrene

Module-VI (6 Hrs.)
Alkaloids
6.1 Natural occurrence, Isolation and their physiological action
6.2 General structural features, experimental determination
6.3 Hoffmann’s exhaustive methylation, Emde’s modification.
6.4 Structure elucidation and synthesis of Hygrine
6.5 Structure elucidation and synthesis of Nicotine.

Assignment 9/Flip class;Medicinal importance of Nicotine, Hygrine, Quinine, Morphine, Cocaine, and Reserpine

Laboratory Practices: (11.30 Hrs.)
7. Qualitative analysis of unknown organic compounds containing simple functional groups: Alcohol

8. Qualitative analysis of unknown organic compounds containing simple functional groups: Carboxylic acids

9. Qualitative analysis of unknown organic compounds containing simple functional groups: Phenols

10. Qualitative analysis of unknown organic compounds containing simple functional groups: Carbonyl compounds (aldehyde) 

11. Qualitative analysis of unknown organic compounds containing simple functional groups: (ketones)

Module-VII (3 Hrs.)
Terpenoids:
7.1 Occurrence, classification, isoprene rule;
7.2 Elucidation of structure and synthesis of Citral, Neral

Assignment 10/Flip class:Elucidation of structure and synthesis of α- terpineol.

Text Books :
1. A Textbook of Organic Chemistry – III, M. K. Jain, S. C. Sharma, Amita, Vishal Publishing Co.
2. Kalsi, P. S. Textbook of Organic Chemistry 1st Ed., New Age International (P) Ltd. Pub.
3. Morrison, R. T. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd. (Pearson Education)
4. Clayden, J.; Greeves, N.; Warren, S.; Wothers, P.; Organic Chemistry, Oxford University Press.

Reference Books :
1. Acheson, R.M. Introduction to the Chemistry of Heterocyclic compounds, John Welly & Sons (1976).
2. Heterocyclic Chemistry, Fifth Edition, J. A. Joule, K. Mills and G. F. Smith
3. Singh, J.; Ali, S.M. & Singh, J. Natural Product Chemistry, Pragati Parakashan (2010).

Session 3

Assignment 1/Flip Class

Application of important nitroarenes

Session 5

Practice 1

Detection of extra elements (Nitrogen containing compound).

lassaigne extract Preparation

https://www.youtube.com/watch?v=foN9ibxBCYU

https://vlab.amrita.edu/?sub=2&brch=191&sim=344&cnt=1

https://www.youtube.com/watch?v=FUo428guKt0

i. Test for Nitrogen

https://www.youtube.com/watch?v=7vKQuWWgULw

Session 6

Practice 2

Detection of extra elements.

Test for Sulfur

https://www.youtube.com/watch?v=F8m3ti2FoAc

Session 7

Practice 3

Detection of extra elements.

Test for Halogens

https://www.youtube.com/watch?v=lGcr_cUmzbY

Session 9

Preparation of secondary and tertiary amines: Aminolysis of alkyl halides, Reductive amination of aldehydes and ketones, Ullmann reaction

https://www.youtube.com/watch?v=NaM_1XvuyLo

Session 11

Practice 4

Test for Functional groups.

Test for Nitro group

https://www.youtube.com/watch?v=n4esSHxz_J8

Session 12

Important reactions of amines: Alkylation, acylation, Carbylamine reaction.

https://www.youtube.com/watch?v=GtyquGq3aSE

Session 14

Assignment 2/Flip Class

Electrophilic substitution reactions of aryl amines

https://www.slideshare.net/ganeshmote1/aromatic-amines

Session 15

Practice 5

Test for Functional groups.

Test for Amine group

https://www.youtube.com/watch?v=j5jgMUWri8U&t=435s

Session 16

Assignment 3/Flip Class

Distinction between 1°, 2° and 3°amines with Hinsberg reagent and nitrous acid.

https://www.youtube.com/watch?v=j5jgMUWri8U

 

Reference:    https://byjus.com/chemistry/hinsberg-reagent-and-test/

Session 18

Practice 6

Test for Functional groups.

Test for Amide group

https://www.youtube.com/watch?v=qARKnpjuQRM

Session 19

Classification, nomenclature and structure of pyrrole, furan and thiophene (5-numbered) and pyridine (6-membered)

https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/heterocy.htm

https://www.slideshare.net/AZCPh/heterocyclic-compounds-organic-chemistry-b-pharm

Session 21

Synthesis, reactions and mechanism of substitution reactions of: Furan, Paal-Knorr synthesis

https://www.organic-chemistry.org/namedreactions/paal-knorr-furan-synthesis.shtm

https://www.slideshare.net/vayuchaurasiya/furan-presentation

Session 22

Synthesis of Pyrrole: Knorr pyrrole synthesis, Paal-Knorr synthesis, Hantzsch synthesis.

http://www.chem.gla.ac.uk/staff/stephenc/teaching/HeterocycleLectures2011_2C12.pdf

Lecture_pyrrole synthesis_reactions

Session 23

Session 24

Assignment 4/Flip Class

Session 27

Structure, synthesis and properties of Pyridine (Hantzsch synthesis) and Pyrimidine.

http://www.chem.gla.ac.uk/staff/stephenc/teaching/HeterocycleLectures2011_2C12.pdf

Lecture_Pyridine_Synthesis_Reactions

Session 31

Assignment 6/Flip Class

Session 33

Preparation and structure elucidation of naphthalene.

Lecture_Naphthalene_Structure and synthesis

Reference: https://www.youtube.com/watch?v=zFyow866BLo

Session 37

Assignment 8/Flip Class

Session 39

General structural features, experimental determination.

https://www.youtube.com/watch?v=nHjURTB0PHY

Lecture_Alkaloids_general_str_elucidation

Session 40

Hoffmann’s exhaustive methylation, Emde’s modification.

https://www.youtube.com/watch?v=nHjURTB0PHY

Session 41

Practice 7

Qualitative analysis of unknown organic compounds containing simple functional groups.

Analysis of Alcohols

https://www.youtube.com/watch?v=xotWCss9bVI

Session 42

Practice 8

Qualitative analysis of unknown organic compounds containing simple functional groups.

Analysis of Carboxylic acids

https://www.youtube.com/watch?v=E2xNpSj_A4U

Session 43

Practice 9

Qualitative analysis of unknown organic compounds containing simple functional groups.

Analysis of Phenols

https://www.youtube.com/watch?v=HSGlfbV7W84

Session 44

Practice 10

Qualitative analysis of unknown organic compounds containing simple functional groups.

Analysis of Carbonyl Compounds (Aldehydes)

https://www.youtube.com/watch?v=X7ZJqLEhX9k

Session 45

Practice 11

Qualitative analysis of unknown organic compounds containing simple functional groups.

Analysis of Carbonyl Compounds (Ketones)

https://www.youtube.com/watch?v=JAQ060bSZG8

Session 46

Structure elucidation and synthesis of Hygrine.

Lecture_Elucidation synthesis_Hygrine

Session 47

Structure elucidation and synthesis of Nicotine.

https://www.youtube.com/watch?v=XQi5qMONbvs

Lecture_Nicotine_Str_Elucidation

Session 48

Assignment 9/Flip Class

Medicinal importance of Nicotine, Hygrine, Quinine, Morphine, Cocaine, and ReserpineStructure elucidation and synthesis of Nicotine.

https://www.slideshare.net/AhmedMetwaly3/alkaloids-lecture-1-introduction

Lecture_Medicinal_Alkaloids

Session 49

Session 51

Assignment 10/Flip Class (2 Hr.)

Elucidation of structure and synthesis of α- terpineol.

https://www.youtube.com/watch?v=FtcL1mOv7WI

Lecture_structure_of a_terpineol

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Our Main Teachers

  Assistant Professor Centurion University of Technology and Management Odisha, India   Teaching  Organic Chemistry Synthetic methods  Stereochemistry  Natural products Research areas/interests  Synthetic methodology  Natural product synthesis  Organocatalysis About Me   Ph.D in Synthetic organic chemistry from National Chemical Laboratory, Pune Research area: Carbohydrate chemistry, Transition metal catalysis, Methodology and total synthesis. Post-doctoral research: Central […]