Mechanistic Organic chemistry

Teacher

Dr. Suchismita Acharya

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Course Name : Mechanistic Organic chemistry

Code(Credit) : CUNT2474(3-1-0)

 

Course objective

  • To have explicit knowledge on mechanistic and conceptual aspects of organic chemistry.
  • To understand the mechanism of organic reactions and reaction behaviors.

Course Outcomes

 

COs Course outcomes Mapping COs with POs (High-3, Medium-2, Low-1)
CO1 After the completion of the course, students will have sound knowledge on concepts of organic chemistry PO1 (3)
CO2 Students will have sound problem solving aptitude in different problems pertaining to organic chemistry. PO3 (3), PO4 (2)
CO3 Able to do research on organic  chemistry and interpret the data for publication PO4 (3)

Course Syllabus

Module-I (4 hrs)

IUPAC nomenclature of organic molecules including regio- and stereoisomers. Principles of stereochemistry: Configurational and conformational isomerism in acyclic and cyclic compounds; stereogenicity, stereoselectivity, enantioselectivity, diastereoselectivity and asymmetric induction.

Module-II (4 hrs)

Aromaticity: Benzenoid and non-benzenoid compounds - generation and reactions. Organic reactive intermediates: Generation, stability and reactivity of carbocations, carbanions, free radicals, carbenes, benzynes and nitrenes.

Module-III (4 hrs)

Organic reaction mechanisms involving addition, elimination and substitution reactions with electrophilic, nucleophilic or radical species. Determination of reaction pathways.

Module-IV (4 hrs)

Common named reactions and rearrangements - applications in organic synthesis.

Module-V (4 hrs)

Organic transformations and reagents: Functional group interconversion including oxidations and reductions; common catalysts and reagents (organic, inorganic, organometallic and enzymatic). Chemo, regio and stereoselective transformations. Concepts in organic synthesis: Retrosynthesis, disconnection, synthons, linear and convergent synthesis, umpolung of reactivity and protecting groups. Asymmetric synthesis: Chiral auxiliaries, methods of asymmetric induction - substrate, reagent and catalyst controlled reactions; determination of enantiomeric and diastereomeric excess; enantio-discrimination. Resolution - optical and kinetic.

Module-VI (4 hrs)

Pericyclic reactions - electrocyclization, cycloaddition, sigma tropic rearrangements and other related concerted reactions. Principles and applications of photochemical reactions in organic chemistry.

Module-VII (6 hrs)

Synthesis and reactivity of common heterocyclic compounds containing one or two heteroatoms (O, N, S).

Chemistry of natural products: Carbohydrates, proteins and peptides, fatty acids, nucleic acids, terpenes, steroids and alkaloids. Biogenesis of terpenoids and alkaloids.

Structure determination of organic compounds by IR, UV-Vis, 1H &13C NMR and Mass spectroscopic techniques Supramolecular chemistry. and medicinal Chemistry.

Practice

  • Estimation of sulphur, nitrogen and functional groups, pharmaceutical analysis.
  • Polyfunctional analysis of organic compounds
  • Preparation of benzanilide by Beckmann rearrangement
  • Preparation of anthranilic acid
  • Preparation of phthalimide
  • Preparation of N- bromosuccinamide
  • Preparatin of p- Amino benzoic acid
  • Preparation of p- chloro nitrobenzene by Sandmeyer reaction
  • Preparation of p- Idonitrobenzene by Sandmeyer reaction
  • Pinacol- Pinacolone rearrangement

Books for Reference

  1. March’s Advanced Organic Chemistry: Reactions, mechanisms, and structure; Michael B. Smith and Jerry March; 6th edition; Wiley-Interscience A John Wiley & Sons, Inc., Publication.
  2. Organic Chemistry; Jonathan Clayden, Nick Greeves& Stuart Warren; 2nd Edition; Oxford University Press.
  3. Pericyclic Reactions and Organic Photochemistry; Vinay P. Sharma, Rakesh Kumar; 1st Edition; Pragati Prakashan.

Session 4:

Aromaticity: Benzenoid and non-benzenoid compounds - generation and reactions.

https://www.youtube.com/watch?v=lVbuBY0YMu4

https://www.youtube.com/watch?v=R6XBNLDamgU

https://www.youtube.com/watch?v=mT1yw0aAl1g

Session 5:

Organic reactive intermediates: Generation, stability and reactivity of carbocations, carbanions, free radicals.

https://www.youtube.com/watch?v=-dEaa1mCfps

https://www.youtube.com/watch?v=DDYJ6piwFVU

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

Session 6:

Organic reactive intermediates: Generation, stability and reactivity of carbenes, benzynes and nitrenes.

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

https://www.youtube.com/watch?v=WjknYNh3z0g

Session 9:

Common named reactions and rearrangements - applications in organic synthesis.

https://www.youtube.com/watch?v=kj33slI9_L8

https://www.youtube.com/watch?v=_MAIveD1zIQ&list=PLYXnZUqtB3K_3NBHR9eyI5SCZmftj8baQ

Session 11:

Organic transformations and reagents: Common catalysts and reagents (organic, inorganic, organometallic and enzymatic)

https://www.youtube.com/watch?v=k1qeD5BICo4

https://www.youtube.com/watch?v=sbMMN50uR3A

https://www.youtube.com/watch?v=9a5AMFop968

Session 12:

Organic transformations and reagents: Chemo, regio and stereoselective transformations.

https://youtu.be/X3pu6qK7oN8

https://youtu.be/B23i9_jC5T8

https://youtu.be/yOH3HtUtZWE

https://youtu.be/XuhqE1NurAU

https://youtu.be/ErpSKI0tcIM

Session 13:

Concepts in organic synthesis: Retrosynthesis, disconnection, synthons, linear and convergent synthesis, umpolung of reactivity and protecting groups.

https://youtu.be/2I5vmNkYTOk

https://youtu.be/cKTwIwVGbzY

https://youtu.be/hDqlx8hJHeQ

https://youtu.be/KjLa5k_kSKc

https://youtu.be/GMrcTrRnLug

https://youtu.be/6uPVXrZ6vYc?list=PL2-xuUUvX2quad1MQ8PbJh-oXrtsaty-k

Session 14:

Asymmetric synthesis: Chiral auxiliaries, methods of asymmetric induction - substrate, reagent and catalyst-controlled reactions.

https://youtu.be/dcXKS9KqwWk

https://youtu.be/fLXyKLVd6Hc

https://youtu.be/A4nW-pSZUNc

https://youtu.be/0ouUT9yX0CM

https://youtu.be/9lUFSvbaXL8

Session 15:

Determination of enantiomeric and diastereomeric excess; enantio-discrimination, resolution - optical and kinetic.

https://youtu.be/LJ1vsyISUpg

https://youtu.be/zAAFIzwjkRM

https://youtu.be/Bj-Q8qnQmlg

https://youtu.be/_UnFJdz4MXc

Session 17:

Principles and applications of photochemical reactions in organic chemistry.

https://youtu.be/DHPXKASQ7LE?list=PLDjIJRH6sIC6Ee5jn67JUbouch4IN0KVJ

https://youtu.be/mEMuWUcJx_4

https://youtu.be/pkq8NDkcgBg

Session 18:

Synthesis and reactivity of common heterocyclic compounds containing one or two heteroatoms (O, N, S).

https://youtu.be/9vMQMQgFhA0

https://youtu.be/ipv_tTFpdtQ

Session 19:

Chemistry of natural products: Carbohydrates, proteins and peptides, fatty acids, nuclei acids, terpenes, steroids and alkaloids.

https://youtu.be/ZYqdAcnJA68

https://youtu.be/OOc3zEgLLtk

https://youtu.be/ajb1z_h0ItU

Session 20:

Biogenesis of terpenoids and alkaloids.

https://youtu.be/oEO9k6aYrOE

https://youtu.be/Fl_bsv1L1-E

Session 21:

Structure determination of organic compounds by IR, UV-Vis, 1H &13C NMR and Mass spectroscopic techniques.

https://youtu.be/2vDAyBCa5NE

https://youtu.be/eu3lmmv6ols

https://youtu.be/JBBLmgVCxrE

Our Main Teachers

Currently working as an Assistant Professor in the department of Chemistry, Centurion University of Technology and Management, Bhubaneswar campus.