Organic Chemistry II (CHEM -373)

Credit Hours:  3+1                                                      Class: BS VI PPP Lhr Campus (2017-2021)  

Introduction to course

• 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.
• 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.
• Classification of elimination reactions. Syn / anti and E1cB eliminations. E1 vs E2. Factors affecting eliminations.
• Electrophilic and nucleophilic substitution reactions at aromatic systems.
• Nucleophilic substitution reactions (SN1, SN2, SNi, SN1', SN2', SNi', Neighbouring group participation etc.) at aliphatic C.
• 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.

Course pre-requisites (if any)

The prerequisites is the Organic Chemistry I (CHEM 372) in minimum grade “C” or better.

Learning outcomes

This course is a foundation course for Reaction Mechanism  and students will  acquire the knowledge about  the classification, methods of determination, kinetic and stereochemical aspects of reaction mechanisms of organic reactions. They will be able to know about the addition to >C=C<, ‒C≡C‒, >C=O, and substitution (nucleophilic & electrophilic) reactions at sp3 & sp2 hybridized C and elimination reactions.

Textbooks to be used for the course

1.March, J., Advanced Organic Chemistry, Wiley, NY. (1992).
2. Pine, S. H., Organic Chemistry, McGraw-Hill, New York. (1987).
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)

Description of system of Evaluation (Exam, assignments etc)

• Attendance    ( Minimum attendance 75% is necessary to appear in the examination)
• behaviour      
• Assignment & presentation
• Sessional                  15%   (Based on attendance,behaviour and assignment and presentations)
• Mid Term Exam          15%
• Project/Practical work: 25%
• Final exam:                 45%

Detailed lesson plans for each lecture (Weekly/Week wise)

Week 1

Introduction and classification of reaction mechanism on different basis

Week 2

Kinetic vs thermodynamic control. Isotopic labeling and trapping of intermediates.

Week 3

Selectivity (Regio-, Chemo- and  Stereoselectivity) vs Stereospecificity

Week 4

Active Methylene Compounds: introduction enolization and acid/base catalyzed aldol condensations.

Week 5

Alkylation, arylation and acylation of Malonic ester

Week 6

Alkylation, arylation and acylation of acetoacetic esterand other ketones.

Week 7

Conditions, mechanism and synthetic applications of  Claisen reaction, Claisen–Schmidt reaction, Knovenagel reaction,

Week 8

Conditions, mechanism and synthetic applications of Reformatsky reaction, Stobbes condensation

Week 9

Mid Term Examination

Week 10

Conditions, mechanism and synthetic applications of Perkin reaction, Darzen‟s glycidic ester synthesis, Mannich reaction and Wittig reaction.

Week 11

Addition reactions involving C=C, C≡C and C=O. Syn vs anti additions.

Week 12

Factors affecting addition reactions. Conjugate (1,4-) vs direct (1,2-) additions.

Week 13

Nucleophilic substitution reactions (SN1, SN2, SNi ) at aliphatic carbon

Week 14

Nucleophilic substitution reactions (SN1', SN2', SNi') at aliphatic carbon

Week 15

Nucleophilic substitution reactions at aromatic systems

 Week 16

Electrophilic and nucleophilic substitution reactions at aromatic systems.

Week 17

Classification of elimination reactions. Syn / anti and E1cB eliminations. E1 vs E2. Factors affecting eliminations.

Week 18

Final Term Examination

Organic Chemistry Lab – II (Cr. 1)

The practical work include single step synthesis of small molecules followed by workup, isolation and purification of product.
Estimation of phenol, acetone and amino groups,

Synthesis of azodyes, iodobenzene, iodoform, sulphanilic acid, cinnamic acid, ethyl benzene

Synthesis of benzil & benzilic acid,

Recommended Books
1. March, J., Advanced Organic Chemistry, Wiley, NY. (1992).
2. Pine, S. H., Organic Chemistry, McGraw-Hill, New York. (1987).
3. Gould, E. S., Mechanism and Structure in Organic Chemistry, Holt, Rinehart &
    Winston, New York. (1959).
4. House, H. O., Modern Synthetic Reactions, Benjamin, California. (1972).

Key dates and time of class meetings

• Semester Start : 10th February 2020

BS Chemistry VI PPP Lhr campus (2017 - 2021)

• Monday  03-4.00 pm
• tuesday  03-04 pm
• Wednesday 03-04 pm
• Thursdaay 03-05   (Practical)