ORGANIC CHEMISTRY II: HALOGEN, OXYGEN AND SULPHUR CONTAINING FUNCTIONAL GROUPS

Paper Code: 
C-CHY 312
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

Course Objective(s):

This course will enable the students to–

develop a perspective towards the mechanistic aspects of different halogen, oxygen and sulphur containing functional groups.

 

Course Outcomes (COs):

Course Outcomes

Teaching Learning Strategies

Assessment Strategies

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

CO40: explain the synthesis and reactivity of various types of aliphatic alcohols (dihydric) and phenols and thiols.

CO41: describe the synthesis and reactivity of ethers, thioethers and epoxides.

CO42: predict the relative reactivity of different carbonyl compounds (saturated and unsaturated aldehydes and ketones) and their syntheses.

CO43: understand the acidity and reactivity of active methylene groups.

CO44: outline the synthesis of carboxylic acids and its derivatives and compare the acidity of carboxylic acids, alcohols and phenols.

CO45:analyse the factors affecting relative reactivity and stability of various carboxylic acids derivatives. 
  • Interactive lectures
  • Tutorials
  • Digital learning
  • Peer learning
  • Problem solving sessions
  • Oral and written examinations
  • Assignments
  • Quiz

 

14.00
Unit I: 
Chemistry of Halogenated Hydrocarbons

Alkyl halides: Methods of preparation, nucleophilic substitution reactions – SN1, SN2 and SNi mechanisms with stereochemical aspects and effect of solvent etc., nucleophilic substitution vs elimination.

Aryl halides: Preparation, including preparation from diazonium salts, nucleophilic aromatic substitution; SNAr, benzyne mechanism.

Relative reactivity of alkyl, allyl/benzyl, vinyl and aryl halides towards nucleophilic substitution reactions, organometallic compounds of Mg and Li: use in synthesis of organic compounds.

14.00
Unit II: 
Alcohols, Phenols, Ethers and Epoxides

Alcohols: preparation, properties and relative reactivity of 1°, 2°, 3° alcohols, Bouvaelt-Blanc reduction, preparation and properties of glycols: oxidation by periodic acid and lead tetraacetate, pinacol-pinacolone rearrangement.

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.

Preparation and reactions of thiols and thioethers.

14.00
Unit III: 
Carbonyl Compounds

Structure, reactivity and preparation, nucleophilic additions, nucleophilic addition-elimination reactions with ammonia derivatives with mechanism, mechanism of aldol and benzoin condensation, Knoevenagel condensation, Claisen-Schmidt, Perkin, Cannizzaro and Wittig reaction, Beckmann and benzil-benzilic acid rearrangements, haloform reaction and Baeyer Villiger oxidation, α-substitution reactions, oxidations and reductions (Clemmensen, Wolff-Kishner, LiAlH4, NaBH4, MPV, PDC and PGC). Addition reactions of unsaturated carbonyl compounds: Michael addition.

Active methylene compounds: Keto-enol tautomerism, preparation and synthetic applications of diethyl malonate and ethyl acetoacetate.

10.00
Unit IV: 
Carboxylic and Sulphonic Acids

Preparation, physical properties and reactions of monocarboxylic acids: Typical reactions of dicarboxylic acids, hydroxy acids and unsaturated acids: succinic/phthalic, lactic, malic, tartaric, citric, maleic and fumaric acids.

Preparation and reactions of sulphonic acids.

8.00
Unit V: 
Carboxylic Acid Derivatives

Preparation and reactions of acid chlorides, anhydrides, esters and amides,comparative study of nucleophilic substitution at acyl group: mechanism of acidic and alkaline hydrolysis of esters, Claisen condensation, Dieckmann and Reformatsky reactions, Hofmann-bromamide degradation and Curtius rearrangement.

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, USA, 2014.
  • Organic Chemistry, Vol. I, Sixth Edition; I.L. Finar; Pearson Education, New Delhi, 2002.
  • Organic Chemistry, Fourth Edition (Indian Edition); G. Marc Loudon, J. Parise; WH Freeman, Oxford University Press, New Delhi, 2008.

e-RESOURCES:

 

Academic Year: 
2023-2024
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