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
Session 2
Frost circle, Aromaticity in benzenoid and non-benzenoid compounds, Huckel’s rule, energy levels of pi-molecular orbitals of simple systems
Session 3
Generation, structure, stability and reactivity ofcarbocations, carbanions
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
Session 8
Session 9
Transition metal reagents
https://www.slideshare.net/ShikhaPopali1/transition-metal-catalysis
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
Session 11
Practice 2 (2Hrs)
Preparation of Benzopinacolone from Benzopinacol
Session 12
Practice 3 (2Hrs)
Benzil to benzilic acid preparation solvent free green synthesis
Session 13
Rearrangements electron deficient nitrogen: Hofman, Curtius, Schimdt, Lossen and Beckmann rearrangement
https://www.youtube.com/watch?v=BF9LufsP69Y
https://www.youtube.com/watch?v=6ucHzMfopfc
https://www.youtube.com/watch?v=DqsZHPU0FWM
Session 14
Rearrangement electron deficient oxygen: Baeyer Villiger rearrangement
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 21
Session 23
Practice 5 (2Hrs)
Resolution of racemic phenylsuccinic acid
Session 26
Session 28
Session 32
Session 33
Retrosynthetic Guidelines for aromatic compounds
Session 34
One group and two group disconnection methods
https://www.youtube.com/watch?v=IHeQZTD8Sy4
Session 35
Examples of synthetic planning using retrosynthetic strategy
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.