Aromaticity and Stereochemistry

Paper Code: 
CHY-202
Credits: 
2
Contact Hours: 
30.00
Max. Marks: 
100.00
Objective: 

Course Objectives:

This course will enable the students to -

  1. understand the core concepts of organic chemistry, resonance, hyperconjugation, inductive effect etc. and other electronic effects including their qualitative and quantitative treatment.

  2. provide an in-depth knowledge about the organic-chemical reactions with a focus on aromaticity & stereochemistry.

Course Outcomes (COs):

Course

Learning outcomes

(at course level)

Learning and teaching strategies

Assessment Strategies

Paper Code

Paper Title

CHY 202

Aromaticity and Stereochemistry (Theory)

 

The students will be able to –

 

CO24: identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties.

CO25: learn and identify many organic reaction mechanisms including  electrophillic aromatic substitution.

CO26: predict and describe various types of reactive intermediates, reactivity and factors affecting the reactivity and stability of aromatic substrates.

CO27: apply the fundamental concepts of stereochemistry on simple molecules.

  • Class lectures

  • Tutorials

  • Group discussions Peer teaching and learning

  • Question preparation

  • Subjective type

  • Long answer

  • Short answer

  • Objective type

  • Multiple choice questions

  • One answer/two answer type questions

  • Assertion and reasoning

  • The oral and written examinations (Scheduled and surprise tests)

  • Closed-book and open-book tests

  • Problem-solving exercises
  • Assignments
  • Quiz
  • Semester End Examination

 

 

5.00
Unit I: 
Aromaticity

Pre requisite: Nomenclature of benzene derivatives (mono and disubstituted), physical properties.

Introduction to aromatic compounds: Benzene, structure and stability, M.O concept, resonance and resonance energy; aromaticity and Hückel’s (4n+2) rule, magnetic criteria.

6.00
Unit II: 
Directing Effects of Substituents

Aromatic electrophilic substitution – general pattern of the mechanism, s and p complexes, energy profile diagram, activating and deactivating effects of substituents, orientation, o/p ratio, halogenation, nitration, sulphonation and desulphonation, Friedel Crafts alkylation and acylation; side chain halogenation of alkyl benzenes (toluene, ethyl benzene), Birch reduction

Self Study: Hydrogenation of benzene derivatives, industrial use of aromatic hydrocarbons.

7.00
Unit III: 
Principles of Stereochemistry

Geometrical isomerism: concept of restricted rotation – cis-trans, syn-anti and E, Z system of nomenclature, geometrical isomerism in oximes, amides and alicyclic compounds. Optical isomerism: elements of symmetry, concept of asymmetry and chirality,  enantiomers and diastereomers, racemic mixture and meso isomers; molecular chirality – allenes, relative and absolute configuration, nomenclature of optical isomers – D,L nomenclature, sequence rule and the R,S system of nomenclature, resolution of enantiomers; elementary concepts of asymmetric synthesis (concept of diastereomeric induction).Elementary concept of chiral induction through chemical reaction (reaction of bromine to alkane and alkenes).

Self Study: Physical properties of enantiomers and diastereomers, optical activity, polarized light, optical activity of enantiomers.

6.00
Unit IV: 
Cycloalkanes

Nomenclature, method of preparation, chemical reactions, theory of strainless rings, cyclopropane and its reactivity with halogens.

6.00
Unit V: 
Conformational analysis: Concept of Free Rotation

Newman, Fischer, Sawhorse and Flying-wedge formula; conformation of ethane, n-butane and cyclohexane – axial and equatorial bonds, conformational analysis of monosubstituted and disubstituted cyclohexane (dimethyl cylcohexane), concepts of conformational locking; chair conformation of α and β glucose and their stability.

References: 

  • Organic Chemistry; Fourth Edition, Indian Edition; G. Marc Loudon; Oxford University Press, New York,2008.
  • Organic Chemistry; Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  • Stereochemistry: Conformation and Mechanism; Eighth Edition; P.S. Kalsi; New Age International Publishers Pvt Ltd, New Delhi, 2015.
  • Organic Chemistry; Seventh Edition; R. T. Morrison, R. N. Boyd, S.K. Bhattacharjee; Pearson Education India, New Delhi, 2010
  • Stereochemistry of Organic compounds; First Edition; Ernest L. Eliel, Samuel H. Wilen; Wiley Interscience,1994.
Academic Year: 
2021-2022
  • Printer-friendly version
  • PDF version