STRUCTURE, REACTIVITY AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS

Paper Code: 
D-CHY 702
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

 Course Objective(s):

This course will enable the students to -

understand the core concepts of organic chemistry i.e. resonance, hyperconjugation, inductive effect etc. and their qualitative and quantitative treatment. The course will also provide an in-depth knowledge about the organic-chemical reactions with a focus on aromaticity, stereochemistry, reactive intermediates and their rearrangements.

Course Outcomes (COs):

Course Outcomes

Teaching Learning Strategies

Assessment

Strategies

On completion of this course, the students will be able to-

CO75: understand the different electronic effects and apply the knowledge  to solve the mechanistic problems

CO76: apply the concepts of configurational and conformational isomerism in different organic compounds.

CO77: identify and differentiate prochirality and chirality at centers, axis, planes and helices and determine the absolute configuration.

CO78: apprise the skeletal and molecular rearrangements involving various reactive intermediates

CO79: differentiate aromatic, nonaromatic, homoaromatic and antiaromatic compounds and interpret their properties.
  • Interactive lectures
  • Tutorials
  • Group discussions
  • Use of models
  • Digital learning
  • Problem solving sessions
  • Assertion and Reasoning

 
  • Oral and written examinations
  • Assignments
  • Quiz

 

 

 

12.00
Unit I: 
Aromaticity

Aromaticity in benzenoid and non-benzenoid compounds, alternant and non-alternant hydrocarbons, Huckel’s rule and Möbius system, energy level of π molecular orbitals in three to eight membered monocyclic systems having conjugation. Annulenes, fullerenes, antiaromaticity, homoaromaticity, PMO approach, steric inhibition to resonance.

12.00
Unit II: 
Structure and Reactivity

A review of types of mechanisms and reactions: Methods of determining reaction mechanism, thermodynamic and kinetic control of reactions, Hammond’s postulate, Curtin- Hammett principle, isotope effects.

Effect of structure on reactivity, resonance effect, field effects & steric effects. Quantitative treatment of the effect of structure on reactivity. The Hammet equation and linear free energy relationship, substituent and reaction constants & Taft equation.

Applications of HSAB principle to organic reactions.

12.00
Unit III: 
Study of Reactive Intermediates

Types, generation, structure, stability, detection and reactivity of the reactive intermediates- carbocation including non-classical carbocation, carbanion, free radical, radical anion, carbene,  nitrene, benzyne, nitrenium ion. Electrophiles and nucleophiles. Molecular rearrangements involving above intermediates viz. Wagner - Meerwein, Pinacol- Semipinacol, Benzil-Benzilic acid, Hoffmann, Curtius, Lossen, Schmidt, Beckmann, Naber, Favorskii, Wittig,  Riemer–Tiemann reaction. Dissolving metal reduction.

12.00
Unit IV: 
Stereochemistry – I

Chirality and asymmetry, molecules with one, two or more chiral centres. Configuration nomenclature, D/L and R/S types of recemates and methods of resolution.

Prochirality: Topicity of ligands and faces and their nomenclature. Stereogenicity, pseudoasymmetry, planar chirality, axial chirality, optical purity, chirogenicity, stereogenic and prochiral centres.

Optical activity in the absence of chiral carbons: biphenyls, allenes, alkyldienes, cycloalkyldienes, spiranes, ansacompounds, adamantanes, and cyclophanes, chirality due to helical shape (P & M), chirality in the compounds containing N, S and P.

12.00
Unit V: 
Stereochemistry – II

Configurations, conformations and stability of cyclohexanes (mono-, di-, and trisubstituted), cyclohexenes, cyclohexanones, halocyclohexanones, decalins, decalols and decalones, effect of conformation on reactivity, strain in cycloalkanes.

Chiral synthesis, stereoselective and stereospecific synthesis, Prelog’s rule, Felkin-anh rule, CD, ORD, octant rule, Cotton effect and their application in determination of absolute and relative configuration and conformation, the axial haloketone rule. Chiral auxiliary and chiral pool.

Essential Readings: 
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  • Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
  • Stereochemistry Conformation and Mechanism, P.S. Kalsi; New Age International, 2005.
  • Organic Chemistry: Vol. I and II, Singh, Mukherjee, Kapoor; Second Edition; New Age International Private Limited, New Delhi, 2018.

 

References: 

SUGGESTED READINGS:

  • Stereochemistry of Organic Compounds , E. L Eliel,. & S. H. Wilen; Wiley, London, 1994.
  • Organic Chemistry, Vol. I, Sixth Edition; I.L. Finar; Pearson Education, New Delhi 2002.
  • Organic Chemistry, Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  • Stereochemistry of Organic Compounds, Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  • Stereochemistry and Mechanism through solved Problems, Third Edition; P. S. Kalsi; New Age International Pvt. Ltd., New Delhi, 2004.

e-RESOURCES:

 

Academic Year: 
2023-2024
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