Mechanism of Organic Reactions and Stereochemistry

Paper Code: 
CHY-212
Credits: 
3
Contact Hours: 
45.00
Objective: 

Course Objectives:

This course will enable the students to –

  1.  apply the core concepts of organic chemistry i.e. resonance, hyperconjugation, inductive effect etc. and their qualitative and quantitative treatment.

  2. have 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-212

 

 

Mechanism of Organic Reactions and Stereochemistry

 

 

The students will be able to –

 

CO35: identify the different aromatic, nonaromatic, homoaromatic & antiaromatic compounds and interpret their properties.

CO36: evaluate the stability of various acyclic and cyclic systems using steric, electronic and stereoelectronic effects and correlate them to reactivity.

CO37: describe various types of reactive intermediates and factors affecting their stability.

CO38: formulate the mechanism of organic reactions by recalling and correlating the fundamental properties of the reactants involved.

CO39: identify and illustrate different organic reaction mechanisms.

CO40: apply the fundamental concepts of stereochemistry.

Class lectures

 

Tutorials

Group discussions

Use of models

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)

• Problem solving exercises

• Assignments

• Quiz

• Semester End Examination

 

8.00
Unit I: 
Aromaticity

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, Huckel’s rule with cyclic carbocations/carbanions and heterocyclic compounds,annulenes& kekulene as examples,elementary idea of aromatic,antiaromatic and homoaromatic compounds. 

8.00
Unit II: 
Aromatic Electrophilic Substitution reactions

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,  One carbon electrophiles reactions: Chloromethylation, Gatterman-Koch, Gatterman, Hoesch, Vilsmeier-Haack reaction, Reimer-Tiemann, Kolbe-Schmidt.

 

12.00
Unit III: 
Aliphatic and Aromatic Nucleophilic Substitution

General preparation and reactions of alkyl halides, Substitution at sp3centre- Mechanism: SN1, SN2, SNi mechanisms with stereochemical aspects, effect of solvent, substrate structure, leaving group, nucleophiles including ambident nucleophiles (cyanide & nitrite) substitution involving NGP.

Aryl halides: Preparation, nucleophilic aromatic substitution; Benzyne mechanism, relative reactivity of alkyl, allyl, benzyl, vinyl and aryl halides towards nucleophilic substitution reactions.

8.00
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; 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)

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 (dimethylcylcohexane), concepts of conformational locking; chair conformation of α and β glucose and their stability.

References: 
  • Stereochemistry: Conformation and Mechanism; Eighth Edition; P.S. Kalsi; New Age International Publishers Pvt Ltd, New Delhi, 2015.
  • Reaction Mechanism in Organic Chemistry; Third Edition; S.M. Mukherjee and S.P. Singh; Laxmi Publications, New Delhi, 2007.
  • Organic Chemistry; Seventh Edition; R. T. Morrison, R. N. Boyd, S.K. Bhattacharjee; Pearson Education India, New Delhi, 2010.
Academic Year: 
2021-2022
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