Structure, Reactivity and Stereochemistry of Organic Compounds

Paper Code: 
CHY-122
Credits: 
4
Contact Hours: 
60.00
Objective: 

Course Objectives :

  • The course aims to make the students 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

Learning outcomes (at course level)

Learning and teaching strategies

Assessment Strategies

Paper Code

Paper Title

CHY 122

Structure, Reactivity and Stereochemistry of Organic Compounds

The students will be able to-

 

CO7- identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties.

CO8- evaluate the stability of various acyclic and cyclic systems using various stereoelectronic effects and correlate their reactivities.

CO9- describe various types of reactive intermediates and factors affecting their stability .

CO10- practice the skeletal and molecular rearrangements involving various reactive intermediates

CO11- identify and differentiate prochirality and chirality at centers, axis, planes and helices and determine the absolute configuration.

CO12- apply various rules for determining stereoselectivity of various organic transformations

 

Interactive lectures

 

Discussions

 

Tutorials

 

Quiz 

 

Problem solving

 

Written test

 

Google quiz

 

Assignment

 

Tutorial

 

Group activity

 

Semester end examination

 
 

 

 

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.

Bonds weaker than covalent: Addition compounds, phase transfer catalysis and crown ethers, cryptands, inclusion compounds, cyclodextrins, catenanes, rotaxanes and Kekulene. H-bonding and its effect on organic compounds.

 

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.

 

References: 
  • Advanced Organic Chemistry: Reactions, Mechanisms and Structure; Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
  • Advanced Organic Chemistry Part A & B; Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
  • Stereochemistry: Conformation and Mechanism; Tenth Edition; P.S. Kalsi; New Age International Publishers Pvt. Ltd, New Delhi, 2019.
  • 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; Singh, Mukherjee, Kapoor; Second Edition; 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 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.

 

Academic Year: 
2021-2022
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