MECHANISMS OF ORGANIC REACTIONS AND STEREOCHEMISTRY

Paper Code: 
CHY 212
Credits: 
3
Contact Hours: 
45.00
Max. Marks: 
100.00
Objective: 

Course Objective(s):

This course will enable the students to –

  • explain aromaticity and stereochemistry of different organic compounds
  • predict the electrophilic and nucleophilic substitution reactions of aliphatic and aromatic substrates.

Course Outcomes (COs):

Course Outcomes

Teaching Learning Strategies

Assessment

Strategies

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

CO40: identify the different aromatic, nonaromatic, homoaromatic and antiaromatic compounds and interpret their properties.

CO41: describe the mechanism of electrophilic aromatic substitution reactions of aromatic hydrocarbons and their derivatives.

CO42: interpret and correlate the reactivity of different alkyl and aryl halides towards substitution reaction.

CO43: apply the concepts of configurational isomerism in different organic compounds.

CO44: illustrate the concept of conformational isomerism and stereochemistry in alkanes and cyclohexane

 
  • Class lectures
  • Tutorials
  • Group discussions
  • Use of models
  • Assertion and reasoning
  • Technology enabled learning
  • Peer learning

 
  • Oral and written examinations
  • Problem solving exercises
  • Assignments
  • Quiz
  • Efficient delivery using seminar presentations
  • Group activity
  • Multiple choice questions
  • Short answer type questions
  • Assertion and reasoning

 

 

 

9.00
Unit I: 
Aromaticity

Nomenclature of benzene derivatives (mono and disubstituted), physical properties, introduction to aromatic compounds, structure and stability of benzene, M.O concept, resonance and resonance energy, aromaticity, Huckel’s rule with cyclic carbocations/carbanions, heterocyclic compounds, annulenes and kekulene, Frost’s diagram, antiaromatic and homoaromatic compounds (elementary approach)

9.00
Unit II: 
Aromatic Electrophilic Substitution Reactions

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 reactions, Friedel-Crafts alkylation and acylation reactions, chloromethylation reaction, Gattermann-Koch reaction, Gattermann reaction, Hoesch reaction, Vilsmeier-Haack reaction, Reimer-Tiemann reaction, Kolbe-Schmidt reaction.
Side chain halogenation of alkyl benzenes (toluene, ethyl benzene), Birch reduction.

9.00
Unit III: 
Aliphatic & Aromatic Nucleophilic Substitution

Alkyl halides- general preparation and reactions, substitution at sp3 centre – mechanism of SN1, SN2, SNi reactions with stereochemical aspects, effect of solvent, substrate structure, leaving group, and nucleophiles on substitution reactions.
Ambident nucleophiles (cyanide & nitrite), substitution reactions involving NGP.
Aryl halides- preparation, nucleophilic aromatic substitution- elimination-addition mechanism (Benzyne mechanism), addition-elimination mechanism.
Relative reactivity of alkyl, allyl, benzyl, vinyl and aryl halides towards nucleophilic substitution reactions.

9.00
Unit IV: 
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, 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 alkanes and alkenes), molecular chirality in allenes.

 

9.00
Unit V: 
Conformational Isomerism- 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 (dimethylcyclohexane), concepts of conformational locking, chair conformation of α and β glucose and their stability.

 

Essential Readings: 
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.

 

References: 

SUGGESTED READINGS:

  • Organic Chemistry, Second Edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2012.
  • Organic Chemistry, Fourth Edition (Indian Edition); G. Marc Loudon, J. Parise; WH Freeman, Oxford University Press, New Delhi, 2008.
  • Organic Chemistry, Twelfth Edition (Global Edition); T. W. Graham Solomons, C. B. Fryhle, S. A. Snyder; Wiley Publishers, United Kingdom, 2017.

e-RESOURCES:

 

 

Academic Year: 
2022-2023
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