Course Title:            Organic Chemistry-II

Course Code:           CHEM-373

Credit Hours:          03+01

 

INTRODUCTION

This course is designed to provide an understanding of the physical organic chemistry and some approaches concerning synthesis of organic molecules. The course will be based upon a problem-solving approach in order to develop the ability to interpret information concerning reaction mechanisms from experimental data and to understand state-of-the-art synthetic approaches in organic synthesis.

 

LEARNING OUTCOMES

This course will enable the students

  • to classify organic reactions mechanism on different basis
  • to apply concepts of physical chemistry in order to solve organic reaction mechanism problems.
  • to have an understanding of different reaction mechanisms common in organic reactions.
  • to develop an understanding of some synthetic approaches in order to synthesize complex organic molecules.

 

CONTENTS

Organic Chemistry – II (Cr.03)

  1. Introduction and classification of reaction mechanism on different basis. Benefits of thermodynamic and kinetic data towards reaction mechanism. Kinetic vs thermodynamic control. Isotopic labeling and trapping of intermediates. Selectivity (Regio-, Chemo- and Stereoselectivity) vs Stereospecificity.
  2. Addition reactions involving C=C, C≡C and C=O. Syn vs anti additions. Factors affecting addition reactions. Conjugate (1,4-) vs direct (1,2-) additions.
  3. Classification of elimination reactions. Syn / anti and E1cB eliminations. E1 vs E2. Factors affecting eliminations.
  4. Electrophilic and nucleophilic substitution reactions at aromatic sytems. Nucleophilic substitution reactions (SN1, SN2, SNi, SN1', SN2', SNi', Neighbouring group participation etc.) at aliphatic C. Th mechanism. 
  5. Active Methylene Compounds: Enolization and acid/base catalyzed aldol condensations. Alkylation, arylation and acylation of acitve methylene compounds. Conditions, mechanism and synthetic applications of the following reactions, Claisen reaction, Claisen–Schmidt reaction, Knovenagel reaction, Perkin reaction, Reformatsky reaction, Stobbes condensation, Darzen’s glycidic ester synthesis, Mannich reaction and Wittig reaction

Organic Chemistry Lab – II (Cr. 01)

Estimation of phenol & acetone, amino groups, synthesis of azodyes, iodobenzene, iodoform, sulphanilic acid, cinnamic acid, benzil & benzilic acid, ethyl benzene.

 

READINGS/BOOKS

  1. Smith, M. and March, J., Advanced Organic Chemistry, Sixth Edition, John Wiley, New York (2007).
  2. Pine, S. H., Organic Chemistry, McGraw-Hill, New York. (1980).
  3. Clayden, Greeves, Warren and Wothers, Organic Chemistry, Oxford, London. (2001).
  4. Gould, E. S., Mechanism and Structure in Organic Chemistry, Holt, Rinehart & Winston, New York. (1959).
  5. House, H. O., Modern Synthetic Reactions, Benjamin, California. (1972).
  6. Sykes, P., A Guide Book to Mechanism in Organic Chemistry, Longman Scientific and Technical, co-published with John Wiley, New York, (1985)
  7. Solomons, T.W.G., Fryhle, C.B., Snyder, S.A., Organic Chemistry, 11th Edition, , John Wiley, New York, (2014).

 

LESSON PLAN

Week 01

Introduction and classification of reaction and reaction mechanism on different basis.

Investigation of Reaction Mechanism: Introduction

Week 02

Nature of Products, Thermodynamic requirements towards reaction mechanism

Week 03

Kinetic data towards reaction mechanism, Steady State Approximation, Kinetic vs thermodynamic control.

Week 04

Study of Intermediates: Isolation, Detection and Trapping

Week 05

Stereochemical studies towards reaction mechanism

Week 06

Isotopic Studies: Isotopic labeling, Isotopic Effect, Isotopic Scrambling

Week 07

Addition reactions involving C=C, C≡C and C=O. Syn vs anti additions. Conjugate (1,4-) vs direct (1,2-) additions.

Week 08

Classification of elimination reactions. E1 vs E2. Syn / anti eliminations

Week 09

MID TERM EXAMINATION

Week 10

E1cB eliminations. Regioselectivity, Pyrolytic Eliminations, Factors affecting eliminations

Week 11

Electrophilic and Nucleophilic substitution reactions at aromatic systems

Week 12

Aliphatic Nucleophilic substitution reactions (SN1, SN2, SNi, SN1', SN2', SNi')

Week 13

Factors affecting Substitution Reactions. Neighbouring group participation

Week 14

Active Methylene Compounds: Enolization and acid/base catalyzed aldol condensations. Alkylation, arylation and acylation of acitve methylene compounds

Week 15

Claisen reaction, Claisen–Schmidt reaction and Wittig reaction,

Week 16

Darzen’s glycidic ester synthesis, Reformatsky reaction and Stobbes condensation,

Week 17

Knovenagel reaction, Mannich reaction and Perkin reaction,.

Week 18

FINAL TERM EXAMINATION

 

SYSTEM OF EVALUATION

  • Mid Exam:    15%
  • Final Exam:  45%
  • Practical       25%
  • Sessional ​    15% (Presentation, Assignment, Attendance, Participation etc,)

 

KEY DATES AND TIME OF CLASS MEETINGS

1.  Class: BS-VI (Regular), Session 2017-2021

     Starting Date: 13-01-2020

     Monday: 11:15 am - 12-15 pm 

    Tuesday: 11:15 am - 12-15 pm 

     Friday:    10:15 am - 11-15 am 

 

2.  Class: BS-VI (Ex-PPP), Section X, Session 2017-2021

     Starting Date: 27-01-2020

     Monday: 02:30 pm - 03-30 pm 

    Tuesday: 02:30 pm - 03-30 pm 

     Friday:    03:30 pm - 04-30 pm 

Course Material