Functionalized Organic Compounds-I (Carbon-Halogen and Carbon- Oxygen/Sulphur Bonds)

Paper Code: 
CHY-302
Credits: 
2
Contact Hours: 
30.00
Max. Marks: 
100.00
Objective: 

Course Objectives:

This course will enable the students to –

  1. learn about reaction and reactivity of some specific functional groups.

Course Outcomes (COs):

Course

Learning outcomes

(at course level)

Learning and teaching strategies

Assessment Strategies

Paper Code

Paper Title

CHY 302

Functionalized Organic Compounds-I

(Carbon-Halogen and Carbon- Oxygen/Sulphur Bonds)

 

 

 

The students will be able to –

 

CO41: predict the products and stereochemistry of nucleophilic substitution reactions (SN1 & SN2) and elimination reactions(E1,E2,E1CB) of alkyl halides

CO42: predict and explain the effect of alkyl, vinyl, aryl and allyl substrates nucleophilic substitution.

CO43: identify the effect of nucleophile, leaving group, substrate and solvent on both substitution and elimination reactions and predict the predominant product

CO44: illustrate the methods of formation and reactivities of various type of aliphatic alcohols (monohydric, dihydric and trihydric) and phenols

CO45: compare the difference in acidity of aliphatic alcohols and phenols

Interactive Lectures

 

Group discussions

 

Tutorials

 

Quiz

 

Problem solving sessions

 

 

 

 

 

 

Multiple choice questions

 

Assertions and reasoning

 

Short answer questions

 

Long answer questions

 

Assignments

 

Quiz

 

 

 

7.00
Unit I: 
Chemistry of Alkyl Halide

Pre requisite: SN2 and SN1 reactions, Saytzeff’s and Hoffmann rules

Substitution reactions: introduction, stereochemistry and factors affecting reactivity in substitution reactions.

Elimination reactions: introduction, β elimination reactions – E2 and E1 reactions, orientation in β elimination reactions.

Substitution v/s elimination.

Self Study: Methods of preparation, other important reactions of alkyl halides.

6.00
Unit II: 
Reactivity of Vinylic, Arylic, Allylic and Benzylic Substrates

Lack of reactivity of vinyl and aryl halide under SN1 andSN2 condition, elimination reaction of vinyl halide.

Nucleophilic substitution reaction of aryl halides: addition-elimination mechanism, elimination-addition (benzyne) mechanism; reactions involving allylic and benzyliccarbocations, allylic and benzylic SN2 reactions.

6.00
Unit III: 
Monohydric Alcohols

Introduction, classification, methods of formation by reduction of aldehydes, ketones, carboxylic acid and esters, biological oxidation of ethanol, hydrogen bonding, acidic nature-comparison with thiols, effect of solvents and polarity, reactions of alcohols.

6.00
Unit IV: 
Dihydric and Trihydric Alcohols

Method of preparation, chemical reactions of vicinal glycols, oxidative cleavage with [Pb(OAc)4] and HIO4;Pinacol- Pinacolone rearrangement.

Trihydric alcohols: introduction, method of preparation andchemical reactions of glycerol

Self Study: Nomenclature

5.00
Unit V: 
Chemistry of Phenols

Introduction, acidic character, comparative acidic strength of alcohol and phenol; reactions of phenols – electrophilic aromatic substitution, acylation and carboxylation, Fries rearrangement, Claisen rearrangement, Gattermann synthesis, Houben–Hoesch reaction, Lederer–Manasse reaction, Reimer-Tiemann reaction.

Self Study: Preparation of phenols.

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.
  • Organic Chemistry; Seventh Edition; R. T. Morrison, R. N. Boyd, S.K. Bhattacharjee; Pearson Education India, New Delhi, 2010.
  • Organic Chemistry. Vol. I and II; Second Edition; S.M. Mukherjee, S.P. Singh, R.P. Kapoor and R. Dass, New Age International Publishers, New Delhi, 2017.
Academic Year: 
2021-2022
  • Printer-friendly version
  • PDF version