Oxygen Containing Functional Groups

Paper Code: 
CHY - 312
Credits: 
3
Contact Hours: 
45.00
Max. Marks: 
100.00
14.00
Unit I: 
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

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 and chemical reactions of glycerol

 

6.00
Unit II: 
Phenols , Ethers and Epoxides

Phenols: Preparation and properties; Acidity and factors effecting it, Ring substitution reactions, Reimer – Tiemann and Kolbe’s – Schmidt Reactions, Fries and Claisen rearrangements with mechanism;

Ethers and Epoxides: Preparation and reactions with acids. Reactions of epoxides with alcohols, ammonia derivatives and LiAlH4

8.00
Unit III: 
Chemistry of Aldehydes and Ketones

Synthesis from acid chlorides, 1,3-dithianes and enamines, nitriles and carboxylic acids;mechanism of nucleophilic addition reaction to carbonyl group with particular emphasis on Benzoin,Perkin, aldol, Knoevenagel condensations,Reformatsky reaction and Dieckman condensation,condensation with ammonia & its derivatives including reactions with primary & secondary amines, Mannich & Wittig reactions.

 

8.00
Unit IV: 
Carbonyl Compounds-II

Oxidation and reduction rections of Aldehydes and ketones :                                          

Use of acetals as protecting groups, oxidation of aldehydes, Baeyer- Villiger oxidation of ketones, Oppenauer oxidation. ,Cannizzaro reaction, MPV,Clemmensen,Wolff-Kishner,LiAlH4,NaBH4 reductions.

Introduction to active methylene group,α,β- unsaturated carbonyl compounds(cyclic & acyclic) , conjugate addition of enolates & amines, , keto-enol tautomerism of ethylacetoacetate,evidences in favour of keto-enol tautomerism, Claisen condensation, alkylation of diethyl malonate & ethyl acetoacetate,

8.00
Unit V: 
Carboxylic Acids and their Derivatives

Preparation, physical properties, acidity and reactions of monocarboxylic acids:

Typical reactions of dicarboxylic acids, hydroxy acids and unsaturated acids: succinic/pthalic, lactic,  tartaric, citric, maleic and fumaric acids.

Preparation and reactions of acid chlorides, anhydrides, esters and amides; comparative study of nucleophilic sustitution at acyl group - mechanism of acidic and alkaline hydrolysis of esters, Dieckmann and Reformatsky reaction, Hoffmann-bromamide degradation and Curtius rearrangement.

 

References: 
  1. Organic Chemistry; Fourth Edition; G. Marc Loudon; Oxford University Press, New York, 2002.
  2.  Organic Chemistry; Seventh Edition; T.W. Graham Solomons & Craig B. Fryhle; John Wiley and Sons, Inc. USA, 1998.
  3. Organic Chemistry; Sixth Edition; Robert Thornton Morrison & Robert Neilson Boyd; Prentice-Hall of India Pvt. Ltd , New Delhi, 2004.
  4. Organic Chemistry; First Edition; Jonathan Clayden, Nick Greeves, Stuart Warren and Peter Wothers; Oxford University Press, USA, 2001.
  5. Organic Chemistry Vol. I ; Fifth Edition; I.L. Finar; Longman Scientific and Technical, Singapore, 1975.