STRUCTURE, REACTIVITY AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS

Paper Code: 
CHY 122
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-

CO6:identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties.

CO7: determine and evaluate the effect of substituents on reactivity using qualitative and quantitative methods.

CO8: describe various types of reactive intermediates and factors affecting their stability.

CO9: practice the use of intermediate in skeletal and molecular arrangement

CO10: identify and differentiate prochirality and chirality at centers, axis, planes and helices and determine the absolute configuration.

 
  • 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 & Reactivity

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.
Qualitative treatment: Resonance effect, field effects & steric effects.
Quantitative treatment: The Hammet equation, linear free energy relationship, substituent and reaction constants, Taft equation.

12.00
Unit III: 
Study of Reactive Intermediates

Types, generation, structure, stability, detection and reactivity of the reactive intermediates- carbocation , non-classical carbocation, carbanion, free radical, radical anion, carbene, nitrene, benzyne, nitrenium ion. Electrophiles and nucleophiles.

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 –

Configuration, chirality and asymmetry, molecules with one, two or more chiral centres, configuration nomenclature, Prelog’s rule, D/L and R/S types of racemates 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

Conformation 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, 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: 
  • 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, Tenth Edition; P.S. Kalsi; New Age International Publishers Pvt. Ltd, New Delhi, 2019.
  • Stereochemistry of Organic Compounds, Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  • A Guidebook to Mechanism in Organic Chemistry, Sixth Edition; P. Sykes; Pearson Education, Delhi, 2011.

 

References: 

SUGGESTED READINGS:

  • Advanced Organic Chemistry Part A & B, Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
  • Physical Organic Chemistry Vol. I and II, Second Edition; N. Isaacs; Longman Scientific and Technical,1995.
  • Named Organic Reactions, Second Edition; T. Lave and A. Plagens; John Wiley and Sons, 2005.
  • Organic Chemistry: Vol. I and II, Second Edition; Singh, Mukherjee, Kapoor; New Age International Private Limited, New Delhi, 2018.
  • Organic Reaction Mechanism, Fourth Edition; V.K. Ahluwalia and R.K. Parashar; Narosa Publishing House, New Delhi, 2002.
  • 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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