CHEM-478 (Organic Synthesis)

The aim of the course is to provide fundamental knowledge of reaction mechanisms in synthetic organic chemistry. The course covers the methods for C-C bond and C-heteroatom bond formation with the basic understanding of selectivity and reactivity of organic molecules. The course will also provide the necessary background to understand the concept of retrosynthetic analysis of simple organic molecules.

LEARNING OUTCOMES

On completion of the course, students will be able to:

  • Demonstrate understanding of the basic principles of bond formations in organic synthesis.
  • Learn how to design strategy to obtain the required selectivity in any organic reactions.
  • Apply the concepts of functional group interconversions (FGIs) and bond formation methodologies for the synthesis of organic molecules.
  • Identify and analyze the fundamentals of bond disconnections and evaluate synthetic routes to target molecules using retrosynthesis.

ASSIGNMENTS

Comprehensive problem sets based on the topic covered during the lecture will be given throughout the semester. Moreover every student will be given a separate topic on modern trends in organic synthesis, for presentation and assignment.

 

RECOMMENDED READINGS

READINGSRR

1.Clayden J., Greeves N., and Warren S. Organic Chemistry, Oxford University Press, New York.

2. Smith M. B., Organic Synthesis, Academic Press, USA

3. Paul WyattStuart Warren, Organic Synthesis, The Disconnection Approach. John Wiley & Sons,, New York

4. March, J., Advanced Organic Chemistry, Wiley, New York.

5Warren S., Designing organic synthesis, John Wiley & Sons, NY

6. Morrison, R. T. and Boyd, N. Organic Chemistry, Allyn & Bacon, London.

 

ASSESSMENT

Sessional:                     20% (presentation+ assignments + class participation)

Mid Term Exam:           30%

Final exam:                   50%

 

              COURSE OUTLINE

 

 

Week

Topics

1.

Introduction and importance of Organic Synthesis. Methods for C – C bond formation, Methods for generation of carbanions

2.

Enolate chemistry for C – C bond formation, Role of medium in alkylation reactions

3.

Kinetic vs Thermodynamic enolat, O vs C-alkylation

4.

Specific enolate equivalents

5.

Michael addition, Mannich Reaction and Robinson annulation

6.

Ylides in C-C bond formation. Other methods like pericylic reactions etc

7.

Methods for C–O, C – N bond formation, Trends in organic synthesis

8.

Introduction and role of protective groups in organic synthesis, Protective groups for carbonyl, alcohols and amines functionalities

9.

Mid Term Exam

10.

Introduction to reterosynthesis, concept of 1,1, 1,2 disconnections, Functional group inter-conversion (FGI)

11.

Disconnections of alcohols and its derivatives

12.

  Disconnections of alkenes

13.

Disconnections of alkanes

14.

Retrosynthesis of difunctionalized compounds

15.

Disconnections of 1,3-dioxygenated compounds

16.

Disconnections of carboxylic acids and simple carbonyl compounds

17.

Disconnections of 1,5-dicarbonyls

18

Practice and exercise of retrosynthesis as well as synthesis of multifunctional organic compounds

 

 

 

 

Course Material