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. Make the students 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 –

CO27: identify the different aromatic, non-aromatic, homoaromatic&antiaromatic compounds and interpret their properties.

CO28: learn and identify many organic reaction mechanisms including  electrophillic aromatic substitution.

CO29: predict and describe various types of reactive intermediates, reactivity and factors affecting the reactivity and stability of aromatic substrates.

CO30: 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, FriedelCrafts 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.

Essential Readings: 
  • 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: 
2020-2021
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