Course Title:    Organic Chemistry-II                                          Course Code: CHEM-6209

Credit Hours:  3+1                                                                    Class: MSc (Regular, 2020-2022)                                          Semester: II (Spring 2021)

Instructor:       Dr Abdul Rauf Raza, Associate Professor              Email: [email protected]

DESCRIPTION & OBJECTIVES

This course (Organic Chemistry-II) focuses on the classification, methods of determination, kinetic and stereochemical aspects of reaction mechanisms of organic reactions. It includes addition (to >C=C<, ‒C≡C‒, >C=O), substitution (nucleophilic & electrophilic) at sp3 & sp2 hybridized C and elimination reactions. This course is a foundation course for Reaction Mechanism (CHEM-663, Organic Chemistry major course of semester-III), Organic Synthesis (CHEM-669, Organic Chemistry major course of semester-IV) and Advance Organic Synthesis (CHEM-750) of MSc and MPhil with organic chemistry specialization.

The practical work involves single step synthesis of small molecules followed by workup, isolation and purification of product.  

READINGS

1.         Clayden, J; Greeves, N; Warren, S., “Organic Chemistry”
            2nd Edition, Oxford University Press, England (2008). Chapter 42 & 43         →        E-copy available

2.         March, J., Advanced Organic Chemistry, Wiley, NY. (1992).

3.         Pine, S. H., Organic Chemistry, McGraw-Hill, New York. (1980).

            4.         Solomons, G. “Organic Chemistry” Edition 7th, McGraw-Hill, New York. (2009).

5.         Hendrickson, Cram, and Hammond “Organic Chemistry” McGraw-Hill Book Co., New York. (1980).

CONTENTS

Theory:

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 systems. Nucleophilic substitution reactions (SN1, SN2, SNi, SN1', SN2', SNi', Neighboring group participation etc.) at aliphatic C. Td mechanism. 

5. Active Methylene Compounds: Enolization and acid/base catalyzed aldol condensations. Alkylation, arylation and acylation of active 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. III (Cr.01)

1. Synthesis of azodyes, iodobenzene (PhI), iodoform (CHI3), sulphanilic acid, cinnamic acid (PhCH=CH-COOH), benzil & benzilic acid, ethyl benzene (PhEt).
2. Estimation of phenol & acetone, amino groups.                                                                                                                                                                                                                                              

COURSE SCHEDULE

RESEARCH PROJECT

Nil

ASSESSMENT CRITERIA

Mid Term Examination:                      15%

Sessional:                                         15%

Project / Practical work:                      25%                

Presentation:                                       included in sessional marks

Participation:                                       Nil 

Final examination:                               45%

RULES AND REGULATIONS

Minimum attendance required for sitting in Mid / Final Exam. = 75%