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Synthesis & Retrosynthesis in Organic Chemistry
Course Objectives :
The aim of the course is to give advanced knowledge in synthetic organic chemistry so that the learner can suggest alternative reagents and reactions for performing desired organic transformations. It is also aimed at making students aware of the basic principles and applications of green chemistry so that they acquire the competence to think, design and develop sustainable chemistry.
Course Outcomes (COs):
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COURSE |
Learning outcomes (at course level) |
Learning and teaching strategies |
Assessment Strategies |
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Paper Code |
Paper Title |
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CHY 321 |
Synthesis & Retrosynthesis in Organic Chemistry |
The students will be able to-
CO88-outline the different processes governing the course of photochemical reactions CO89- distinguish between thermal and photochemical energies and their effect on the course of chemical reactions. CO90- comprehend the orbital interactions and orbital symmetry correlations of various pericyclic reactions. CO91- explain various pericyclic reactions i.e. Electrocyclic reactions, Cycloaddition reactions and Sigmatropic reactions. CO92- predict structures of the products based on the reaction conditions and reagents used in pericyclic reactions. CO93- discuss the concepts related to synthesis, mechanisms and the functions of various reagents. CO94- hypothesize retrosynthetic methods for the logical dissection of complex organic molecules and devise synthetic methods
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Interactive lectures
Discussions
Tutorials
Problem solving |
Written test
Quiz
Assignment
Tutorial
Group activity
Semester end examination
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Laws of photochemistry. Fate of excited molecules - Jablonskii diagram, intersystem crossing, energy transfer, photosensitization, quenching, quantum yield, Stern-Volmer equation. Photochemical reactions of ketones – alpha cleavage or Norrish type I cleavage, gamma hydrogen transfer or Norrish type II cleavage; photo reductions; Paterno-Buchi reactions; Photochemistry of α,β-unsaturated ketones, β,γ-unsaturated ketones, cyclohexadienones (cross conjugated and conjugated).
Photochemistry of alkenes: Intramolecular reactions of the olefinic bond – cis-trans isomerisation (stilbene), cyclization reactions, rearrangement of 1,4 and 1,5-dienes, di-π methane rearrangement.
Photochemistry of aromatic compounds: Photochemical rearrangement, photostationary state, 1, 3, 5 – trimethyl benzene to 1, 2, 4-trimethyl benzene.
Miscellaneous Photochemical Reactions: Barton reaction, photo Fries rearrangement of ethers and anilides, singlet oxygen reactions (photo oxygenation).
General characteristics, classification, molecular orbital symmetry.
Electrocyclic reactions: theories of explanation (FMO, Woodword-Hoffmann and PMO approach), frontier orbitals, electrocyclisation and reterocyclisation of 1,3 butadiene, cyclobutadiene and hexatriene derivatives, allylic cations (1,5 diphenylpentadienyl cation) and allylic anions (1,5 diphenylpentadienyl anion), ring opening in bicycle [4.1.0] heptane derivatives, valence tautomerism.
Cycloaddtion reactions: 2+2, 4+2 cycloaddition, 1, 3-dipolar cycloaddition and cheletropic reactions; stereoselectivity (endo, exo), stereospecific and regioselective hydrogen reactions, Lewis-acid catalysis in Diels’ Alder reaction.
Sigmatropic rearrangements: Suprafacial and antarafacial shifts of H, sigmatropic shifts involving carbon moieties, 3, 3- and 5, 5-sigmatropic rearrangements; Claisen, Cope and Aza-Cope rearrangements; Isomerization of divinyl cyclopropane; Fluxional tautomerism (bullvalene); Ene reaction.
Synthons and synthetic equivalents, Types-d1, d2, d3 and d4 synthons, disconnection approach, functional group inter-conversions, the importance of the order of events in organic synthesis, one group C-X and two group C-X disconnections, chemoselectivity, reversal of polarity, cyclisation reactions, amine synthesis; principle of protection of alcohol, amine, carbonyl and carboxyl groups.
One and Two Group C-C Disconnections
Alcohols and carbonyl compounds, regioselectivity, alkene synthesis, uses of alkynes and aliphatic nitro compounds in organic synthesis; Diels’ Alder reaction, 1,3-difunctionalised compounds, α,β-unsaturated carbonyl compounds, control in carbonyl condensations, 1,5-difunctionalised compounds, Michael addition and Robinson annelation.
- CRC Handbook of Organic Photochemistry and Photobiology; Second Edition; W. Horspool and F. Lenci; CRC Press LLC, US, 2004.
- Fundamentals of Photochemistry; Third Edition; K.K. Rohatagi and Mukherjee; New Age International Publishers Pvt. Ltd., New Delhi, 2007.
- Molecular Reactions and Photochemistry; First Edition; C. H. Depuy and L. Orville Chapman; Prentice-Hall of India Pvt. Ltd, New Delhi, 1988.
- Reaction Mechanism in Organic Chemistry; Third Edition; S.M. Mukherjee and S.P. Singh; Macmillan, India Ltd., New Delhi, 2003.
- Advanced Organic Chemistry Part A & B; Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
- Designing Organic Synthesis: A Programmed Introduction to the Sython Approach; First Edition; S. Warren; John Wiley and Sons, Great Britain, 2010.
- Organic Synthesis- Concepts, Methods and Starting Materials; J. Fuhrhop and G.Penzillin; Second Edition; Wiley-Vch, New York: 2003.
- Modern Methods of Organic Synthesis; Fourth Edition; W. Carruthers; Cambridge Univ. Press, UK, 2005.
