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

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

Session Plan

Session 1:

IUPAC nomenclature of organic molecules including regio- and stereoisomers.

https://www.youtube.com/watch?v=8ddPyrooqAo

https://www.youtube.com/watch?v=d7F3mGZRi9g

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

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

https://www.youtube.com/watch?v=-6kfIRp8NWY

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

Session 2:

Principles of stereochemistry: Configurational and conformational isomerism in acyclic and cyclic compounds.

https://www.youtube.com/watch?v=WuU7m0LT-uM

https://www.youtube.com/watch?v=UCM9EW_LVYg

https://www.youtube.com/watch?v=JT3FuQjuLN8

https://www.youtube.com/watch?v=_Pb97L6JQ68

https://www.youtube.com/watch?v=iRD8iu_TBZM

https://www.youtube.com/watch?v=r5TTgCEiC6c

Session 3:

Stereogenicity, stereoselectivity, enantioselectivity, diastereoselectivity and asymmetric induction.

https://www.youtube.com/watch?v=XHopLI4X2EE

https://www.youtube.com/watch?v=QRIcf1cNzf8

https://www.youtube.com/watch?v=BknceUDDHM0

https://www.youtube.com/watch?v=1xCiMl8lR20

https://www.youtube.com/watch?v=itkSddRRBfU&list=PLXFnB8P_BQpZfxUI0wkZlcK9JvIK-bmo0

https://www.youtube.com/watch?v=wQIEeOAJ47c&list=PLXFnB8P_BQpZfxUI0wkZlcK9JvIK-bmo0&index=2

https://www.youtube.com/watch?v=mlS68Xk7U-k

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 7:

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

https://www.youtube.com/watch?v=nKK8WKyz0pk

https://www.youtube.com/watch?v=RLM6CzQsT7w

https://www.youtube.com/watch?v=z2BSRLxMBng

https://www.youtube.com/watch?v=K-7-r-1FbXw

https://www.youtube.com/watch?v=yYiYt4jdaIY

https://www.youtube.com/watch?v=V40WLuhHpoE

Session 8:

Determination of reaction pathways.

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

https://www.youtube.com/watch?v=56X6qk9eEsw

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 10:

Organic transformations and reagents: Functional group interconversion including oxidations and reductions.

https://www.youtube.com/watch?v=EtnD5I2V4a8

https://www.youtube.com/watch?v=TvefNUmu3oc

https://www.youtube.com/watch?v=FudSIAXh4fg

https://www.youtube.com/watch?v=7XVv-S5F0mU

https://www.youtube.com/watch?v=1mZUlluWaoQ

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