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IIS Univ
  • Admissions

    It is a University which is committed to excellence and overall development of the student...

  • Placements

    Excellent education not only imparts knowledge, but also paves the way for...

  • Life@IIS Univ

    Life @ IISU is nothing less than a kaleidoscope of myriad hues; complete with...

  • Academics

    Taking the age-old tradition of enlightenment through education forward,...

  • Research

    To stimulate curiosity and cater to the global needs of a dynamic education,...

  • About Us

    The IIS University, with its perfect amalgamation of innovation, inspiration...

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Photochemistry, Pericyclic Reactions and Disconnection Approach | Chemistry

Photochemistry, Pericyclic Reactions and Disconnection Approach

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Paper Code: 
25CHY321
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

This course will enable the students to

acquire in-depth knowledge of various photochemical reactions and their basic principles which enables students to learn a variety of photochemical reactions, and their mechanisms and understand the various organic transformations through the disconnection approach.

 

Course Outcomes: 

Course

Learning outcome

(at course level)

Learning and Teaching Strategies

Assessment Strategies

Course Code

Course

Title

 

25CHY321

 

Photochemistry, Pericyclic Reactions and Disconnection Approach

(Theory)

CO95 Distinguish between thermal and photochemical reactions and explain the photochemistry of carbonyl compounds.

CO96 Explain the various photochemical reactions of alkenes and aromatic compounds along with singlet oxygen reactions.

CO97 Appraise the orbital interactions and orbital symmetry correlations in electrocyclic reactions to solve various problems.

C098 Explain and justify pericyclic reactions and their products in cycloaddition and sigmatropic reactions.

C099 Justify retrosynthetic methods for the logical dissection of complex organic molecules and devise appropriate routes for their synthesis. Predict logical uses of various reagents in organic synthesis.

CO100 Contribute effectively in course-specific interaction.

Approach in teaching:

Interactive lectures, tutorials, group discussions and e-learning.

 

Learning activities for the students:

Peer learning, e- learning, problem solving through tutorials and group discussions.

 

 

Written examinations,

Assignments, Quiz

 

 

12.00
Unit I: 
Basics of Photochemistry and Photochemical Reactions of Carbonyl Compounds

Laws of photochemistry. Fate of excited molecules: Jablonski 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).

 

10.00
Unit II: 
Photochemistry of Alkenes and Aromatic Compounds

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 methanerearrangement.

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).

 

10.00
Unit III: 
Pericyclic Reactions -I

General characteristics, classification, molecular orbital symmetry.

Electrocyclic reactions: Theories of explanation (FMO, Woodward-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 bicyclo [4.1.0] heptane derivatives, valence tautomerism.

 

10.00
Unit IV: 
Pericyclic Reactions–II

Cycloaddition 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.

 

18.00
Unit V: 
Disconnection Approach in Organic Synthesis

Disconnection approach, Synthons and synthetic equivalents, d, d, dand dsynthons, , 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 carboxylgroups.

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.

 

Essential Readings: 
  1. Fundamentals of Photochemistry, Third Edition; K.K. Rohatagi and Mukherjee; New Age International Publishers Pvt. Ltd., New Delhi, 2007.
  2. Reaction Mechanism in Organic Chemistry, Third Edition; S.M. Mukherjee and S.P. Singh; Macmillan, India Ltd., New Delhi, 2003.
  3. Modern Methods of Organic Synthesis, Fourth Edition; W. Carruthers; Cambridge Univ. Press, UK, 2005.

 

References: 
  1. CRC Handbook of Organic Photochemistry and Photobiology, Second Edition; W. Horspool and
  2. F. Lenci; CRC Press LLC, US, 2004.
  3. Molecular Reactions and Photochemistry, First Edition, C. H. Depuy and L. Orville Chapman; Prentice-Hall of India Pvt. Ltd, New Delhi, 1988.
  4. Advanced Organic Chemistry Part A & B, Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
  5. Designing Organic Synthesis: A Programmed Introduction to the Sython Approach, First Edition; S. Warren; John Wiley and Sons, Great Britain, 2010.
  6. Organic Synthesis- Concepts, Methods and Starting Materials, J. Fuhrhop and G.Penzillin; Second Edition; Wiley-VCH, New York: 2003.

 

e-Resources:

  1. https://epgp.inflibnet.ac.in/Home/ViewSubject?catid=13G8VouhmrFfuhs6rkiyTA== (P-14)
  2. https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/photchem.htm (Photochemistry)
  3. https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/pericycl.htm#top1 (Pericyclic reactions)
  4. https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/synth1.htm#top2 (Disconnection approach)

 

Academic Year: 
2025-2026
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