HALOGEN AND OXYGEN CONTAINING FUNCTIONAL GROUPS

Paper Code: 
CHY 301
Credits: 
3
Contact Hours: 
45.00
Max. Marks: 
100.00
Objective: 

Course Objectives:

This course will enable the students to –

  • explain the reactivity of alkyl halides
  • develop a perspective towards the mechanistic aspects of different oxygen containing functional groups

 

Course Outcomes (COs):

Course Outcomes

Teaching learning strategies

Assessment

Strategies

  
 

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

CO31: describe the synthesis and reactivity of alkyl halides

CO32: explain the synthesis and reactivity of various type of aliphatic alcohols (monohydric, dihydric and trihydric) and phenols 

CO33: predict the relative reactivities of different carbonyl compounds (saturated and unsaturated aldehydes and ketones) and their syntheses.

CO34: interpret the mechanism of  prescribed name reactions

CO35: understand the acidity and reactivity of active methylene groups

CO36: outline the synthesis of carboxylic acids and its derivatives and compare the acidity of carboxylic acids, alcohols and phenols

CO37: analyze the factors affecting relative reactivity and stability of various carboxylic acids derivatives. 

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

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

 

  

 

9.00
Unit I: 
Chemistry of Halogenated Hydrocarbons

Alkyl halides - nucleophilic substitution reactions – SN1 and SN2 mechanisms with kinetic and stereochemical aspects, effect of substrate, solvent and nucleophiles.
Aryl halides-  nucleophilic aromatic substitution – addition-elimination, elimination-addition (benzyne mechanism), relative reactivity of alkyl, allyl/benzyl, vinyl and aryl halides towards nucleophilic substitution reactions.
Self-Study: Methods of preparation of alkyl and aryl halides

 

9.00
Unit II: 
Alcohols & Phenols

Alcohols- chemical reactions, 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- properties, acidity and factors effecting it, ring substitution reactions- Reimer–Tiemann and Kolbe’s–Schmidt Reactions, Fries and Claisen rearrangements (with mechanism).
Self-Study: methods of preparation of alcohols and phenols.

 

9.00
Unit III: 
Carbonyl Compounds I

Synthesis from acid chlorides, 1,3-dithianes and enamines, pyridinium chlorochromate (PDC), Pyridinium chlorochromate (PCC), nitriles and carboxylic acids.
Mechanism of nucleophilic addition reaction to carbonyl group with particular emphasis on benzoin, Perkin, aldol, Knoevenagel, Reformatsky reaction, Benzil-Benzilic acid rearrangement.
Condensation with ammonia & its derivatives including reactions with primary & secondary amines, Mannich & Wittig reactions.

 

9.00
Unit IV: 
Carbonyl Compounds II

Addition reactions of unsaturated carbonyl compounds- Michael addition.
Use of acetals as protecting groups. Oxidation of aldehydes, Baeyer-Villiger oxidation of ketones, Oppenauer oxidation, Cannizzaro’s reaction, MPV, Clemmensen, Wolff-Kishner, LiAlH4, NaBH4 reductions.
Active methylene compounds- Keto-enol tautomerism, preparation and synthetic applications of diethyl malonate and ethyl acetoacetate.

 

9.00
Unit V: 
Carboxylic Acids & their Derivatives

Preparation, physical properties and reactions of monocarboxylic acids, acidity and factors affecting it.
Preparation and Reactions of acid chlorides, anhydrides, esters and amides, relative reactivity and stability of carboxylic acid derivatives.

 

Essential Readings: 
  • Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
References: 

 

SUGGESTED READING:

 

 

  • Organic Chemistry, Second edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2014.
  • 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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