CHEMISTRY OF HYDROCARBONS & STEREOCHEMISTRY

Paper Code: 
CHY 202
Credits: 
3
Contact Hours: 
45.00
Max. Marks: 
100.00
Objective: 

Course Objective(s):

This course will enable the students to-

  • explain the electronic effects and their qualitative and quantitative treatment.
  • acquire in-depth knowledge of structure, bonding, reactivity and reaction mechanisms of alkanes, cycloalkanes, alkenes & alkynes.
  • explain aromaticity and stereochemistry of different organic compounds

Course Outcomes (COs):

Course Outcomes

Teaching Learning Strategies

Assessment

Strategies

  
 

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

 

CO23: apply the knowledge of different electronic effects to solve the mechanistic problems

CO24: describe the structure, stability, reactivity and mechanistic ability of various saturated and unsaturated hydrocarbons

CO25: predict the products of reactions given by saturated & unsaturated hydrocarbons.

CO26: apply the concepts of configurational isomerism in different organic compounds.

CO27: illustrate the concept of conformational isomerism and stereochemistry in alkanes and cyclohexane

CO28: identify the different aromatic, nonaromatic, homoaromatic & antiaromatic compounds and describe the mechanism of electrophilic aromatic substitution reactions of aromatic hydrocarbons and their derivatives.

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

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

 

 

  

 

 

9.00
Unit I: 
Alkanes & Cycloalkanes

Alkanes- introduction to hydrocarbons, branched and unbranched alkanes, physical properties.
Reactivity of alkanes- bond dissociation energies, halogenation with special reference to generation and stability of free radicals, reactivity and selectivity, energy profile diagram.
Cycloalkanes- nomenclature, chemical reactions, Baeyer strain theory, concept of banana bond, addition to cyclopropane ring, theory of strainless rings.
Conformational isomerism- Newman, Fischer, sawhorse and flying-wedge formula, conformation of ethane and n-butane.
Cyclohexane – axial and equatorial bonds, conformational analysis of monosubstituted cyclohexane.
Self-Study- methods of preparation of alkanes and cycloalkanes.

 

9.00
Unit II: 
Chemistry of Alkenes

Pre-requisite-hybridization of carbon, cis-trans isomerism, IUPAC nomenclature, general methods of preparation, physical properties.
Structure and bonding in alkenes, heat of hydrogenation, methods of formation – dehydration of alcohols (formation of carbocation, structure and stability), dehydrohalogenation of alkyl halide, relative stability of alkene isomers by Saytzeff’s rule and Hoffmann’s rule, regioselectivity.
Mechanism involved in hydrogenation, electrophilic and free radial addition, Markovnikov’s rule, oxidation with KMnO4 and OsO4, hydroboration-oxidation, ozonolysis, oxymercuration-reduction.

 

9.00
Unit III: 
Chemistry of Dienes & Alkynes

Dienes- structure and stability of conjugative and cumulative dienes, resonance and molecular orbital structure of allene and 1,3-butadiene, addition of hydrogen halides to conjugated dienes – 1,4 v/s 1,2 addition (formation, structure and stability of allylic carbocation and free radicals). Diels’ Alder reaction.
Alkynes- structure and stability, acidity of alkynes, mechanism of electrophilic addition reactions, reduction of alkynes – catalytic hydrogenation, dissolving metal reduction, nucleophilic addition reactions.
Self-Study: Industrial applications of alkynes.

 

9.00
Unit IV: 
Aromatic Hydrocarbons

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, Huckel’s rule with cyclic carbocations/carbanions, elementary idea of aromatic, antiaromatic and homoaromatic compounds.
Electrophilic aromatic substitution- halogenation, nitration, sulphonation and Friedel-Craft’s alkylation/acylation with their mechanism.
Directing effects of substituent groups, o/p ratio.

 

9.00
Unit V: 
Stereochemistry

Geometrical isomerism - cis–trans and, syn-anti isomerism, E/Z notations with C.I.P rules.
Optical Isomerism - optical activity, specific rotation, chirality/asymmetry, enantiomers, molecules with two or more chiral-centres, diastereoisomers, meso structures, racemic mixtures, relative and absolute configuration- D/L and R/S designations.

 

Essential Readings: 
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  • Stereochemistry: Conformation and Mechanism, Tenth Edition; P.S. Kalsi; New Age International   Publishers Pvt. Ltd., New Delhi, 201

References: 

 

 

SUGGESTED READINGS:

  • Organic Chemistry, Second Edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2012.

  • Organic Chemistry, Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  • 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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