Synthetic Organic Chemistry

Teacher

Rajesh Mishra

Category

Core Courses

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Course Name : Synthetic Organic Chemistry

Code(Credit) : CUTM1423 (3-1-0)

Course Objectives

To understand various reagents and rearrangements and their mechanism involved in various reactions.
To understand and explain the stereochemical aspects of organic compounds and stereoselective reactions
To understand how to design complex molecules by retrosynthetic methods

Learning Outcomes

After finishing the course the student will gain:

Expertize in rearrangements reactions and the mechanism involved.
Expertize in writing conformational structures.
Expertise in designing and planning synthesis of complex molecules

Course Syllabus

Module I

Fundamentals        (4Hrs)

Delocalized chemical bonding, Conjugation, Cross conjugation, Resonance, Hyperconjugation, Bonding in fullerenes, Tautomerism

Frost circle, Aromaticity in benzenoid and non-benzenoid compounds, Huckel’s rule, energy levels of pi-molecular orbitals of simple systems.

Generation, structure, stability and reactivity ofcarbocations, carbanions
Generation, structure, stability and reactivity of Free radicals, carbenes and nitrenes.

Module II

Organic Reagents             (4Hrs)           

Oxidising agents
Reducing agents
Organometallic reagents
Transition metal reagents
Practice (1 Hr)

1. Preparation of dibenzalacetone by Aldol Reaction

Module III

Molecular Rearrangement        (5Hrs)

Rearranments: Rearrangement to electron deficient carbon: Pinacol-pinacolone, Wagner-Meerwein, Benzillic acid and Demjanov rearrangement
Rearrangements electron deficient nitrogen: Hofman, Curtius, Schimdt, Lossen and Beckmann rearrangement
Rearrangement electron deficient oxygen: Baeyer Villiger rearrangement
Rearrangements to electron rich carbon: Fovorskii, Wittig, Neber, Steven’s and Sommelet Houser rearrangement
Aromatic rearrangements: Fries, Clasisen and Benzidine rearrangement and Free radical rearrangements

Practice (4 Hrs)

2. Preparation of Benzopinacolone from Benzopinacol

3. Benzil to benzilic acid preparation solvent free green synthesis

Module IV                (4Hrs)

Stereochemistry

Coformational Isomers of cyclohexane
Cofigurational Isomerism
Absolute and relative stereochemistry
Atropisomerism

Practice (4 Hrs)

4. Cis-trans isomerism of alkene

5. Resolution of racemic phenylsuccinic acid

Module V                (5Hrs)

Photochemistry

Electronic transitions
Photochemical reactions
Photochemical reductions
Photochemical rearrangement
Asymmetric Synthesis

Module VI                (4Hrs)

Pericyclic Reaction

Woodward Hoffman rule, FMO theory
Electrocyclic reactions
Cycloaddition reactions
Sigmatropic and group transfer reactions

Module VII

Retrosynthesis                  (4Hrs)

Retrosynthetic Terminology
Retrosynthetic Guidelines for aromatic compounds
One group and two group disconnection methods
Examples of synthetic planning using retrosynthetic strategy

Practice (2 Hrs)

6. Synthesis of Aspirin

References:

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
Organic Chemistry; Jonathan Clayden, Nick Greeves & Stuart Warren; 2nd Edition; Oxford University Press
Pericyclic Reactions: A Mechanistic and Problem-Solving Approach; Sunil KumarVinod Kumar P. Singh; 1st Edition
Pericyclic Reactions and Organic Photochemistry; Vinay P. Sharma, Rakesh Kumar; 1st Edition; Pragati Prakashan

Session Plan

Session 1

Delocalized chemical bonding, Conjugation, Cross conjugation, Resonance, Hyperconjugation, Bonding in fullerenes, Tautomerism

https://www.youtube.com/watch?v=FIUGYR5mGcQ

https://www.youtube.com/watch?v=pHGCjL6mz_A

Session 2

Frost circle, Aromaticity in benzenoid and non-benzenoid compounds, Huckel’s rule, energy levels of pi-molecular orbitals of simple systems

https://www.youtube.com/watch?v=Df5Ss3rPs_c

https://www.youtube.com/watch?v=U6FX5RfLjd0

Session 3

Generation, structure, stability and reactivity ofcarbocations, carbanions

https://www.youtube.com/watch?v=_mEJ1aYmYo4&t=515s

Session 4

Generation, structure, stability and reactivity of Free radicals, carbenes and nitrenes

https://www.youtube.com/watch?v=UTovNkVQ7tY

https://www.slideshare.net/VIKASMATHAD1/free-radicals-84891258

Session 7

Practice 1 (2Hrs)

Preparation of Dibenzalacetone by Aldol reaction

https://www.youtube.com/watch?v=yfy57Gc8VfM

Session 10

Rearranments: Rearrangement to electron deficient carbon: Pinacol-pinacolone, Wagner-Meerwein, Benzillic acid and Demjanov rearrangement

https://www.youtube.com/watch?v=C2HNpZUDqOk

https://www.youtube.com/watch?v=JI3oPULchI8

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

https://www.youtube.com/watch?v=PyxZpXZM4dM

Session 11

Practice 2 (2Hrs)

Preparation of Benzopinacolone from Benzopinacol

https://www.youtube.com/watch?v=9bElvg9t13k&t=21s

Session 12

Practice 3 (2Hrs)

Benzil to benzilic acid preparation solvent free green synthesis

https://www.youtube.com/watch?v=3sWzhW2F-kQ

Session 14

Rearrangement electron deficient oxygen: Baeyer Villiger rearrangement

https://www.youtube.com/watch?v=f45IiJ3-_ns

Session 15

Rearrangements to electron rich carbon: Fovorskii, Wittig, Neber, Steven’s and Sommelet Houser rearrangement

https://www.slideshare.net/kumarbodapati/wittig-reaction-32272558

Session 16

Aromatic rearrangements: Fries, Clasisen and Benzidine rearrangement and Free radical rearrangements

https://www.slideshare.net/ApoorvRastogi7/claisen-rearrangement-87859707

Session 19

Practice 4

Cis-trans isomerism of alkene

https://www.youtube.com/watch?v=Jz33rBxxsqU

Session 20

Absolute and relative stereochemistry

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

Session 23

Practice 5 (2Hrs)

Resolution of racemic phenylsuccinic acid

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

Session 24

Session 27

Photochemical rearrangement

https://www.youtube.com/watch?v=NGlUiL8sjws

Session 29

Session 31

Session 33

Retrosynthetic Guidelines for aromatic compounds

https://www.youtube.com/watch?v=feg4RqF-xCA

Session 35

Examples of synthetic planning using retrosynthetic strategy

https://www.slideshare.net/munirnizami/protecting-groups

Session 36

Practice 6 (2Hrs)

Synthesis of Aspirin

https://www.youtube.com/watch?v=Y4NMpO1xI8U

Case Studies

Our Main Teachers

Rajesh Mishra, working as Asst. Prof in the Dept. of Chemistry from 2013 at CUTM, Balangir Campus. He has more than 8 years of teaching experience in the field of Oranic Chemistry, organic synthesis and natural products.