COURSE OUTLINE FALL 2020
Course Title: Advance Stereochemistry
Course Code: CHEM-7139
Credit Hours: 3
Instructor: Dr Abdul Rauf Raza, Associate Professor
Email: [email protected]
DESCRIPTION & OBJECTIVES
Stereochemistry is the study of the relative arrangement of atoms or groups in a molecule in 3D space. Stereochemistry of molecules dictates isomerism, chemical and biochemical reactivity. These days chiral drugs have become an integral part of pharmaceutical industry and replacing racemic (enantio impure) drugs. A basic concept on 3D structures, conformations of molecules, asymmetric synthesis, other stereochemical principles and attributes are essential.
This course is aimed at our BS/MSc course CHEM-372 / 561 (Organic Chemistry-I) course as foundation knowledge. This course (CHEM-740, Advance Stereochemistry) shall lay foundation for asymmetric transformations with an emphasis on mechanisms, structure-reactivity relationships and applications in organic synthesis.
READINGS
- Eliel, E. L. Wilen S. H. and Mander, L. N. Stereochemistry of Organic Compounds. John Wiley & Sons, New York (1994).
- Morris, D. G. Stereochemistry. RSC (Cambridge), UK (2001).
- North, M. Principles and Applications of Stereochemistry. Stanley Thornes Publishers Ltd (Cheltenham), UK (1998).
- Nasipuri, D. Stereochemistry of Organic Compounds: Principles and Applications. New Age International Ltd, New Delhi (2012).
- Gal, J., Stereochemical Vocabulary for Structures …. Chirality, 23 (2011), 647-659 (A review article).
CONTENTS
Stereochemistry of cyclic and fused systems; stereochemical outcome of addition, substitution, elimination, pericyclic reactions and molecular rearrangements; Felkin-Anh’s Principle; ee and de; stereoselectivity vs stereospecificity; asymmetric syntheses involving the use of chiral pool, chiral reagents and chiral catalysts, resolution methods.
COURSE SCHEDULE
|
Week |
Topics and Readings |
Dates |
|
1 |
Polarimetry, elements of symmetry (Cn, σv, σh, Sn) |
November 2, 2020 |
|
Elements of chirality, classification of isomers |
November 3, 2020 |
|
|
2 |
Projection of 3D models (molecules) to 2D |
November 9, 2020 |
|
Configuration vs conformation; relative & absolute configuration |
November 10, 2020 |
|
|
3 |
Topicity of ligands, faces & surfaces |
November 16 & 17, 2020 |
|
4 |
Cyclic & fused (decalene etc.) ring systems |
November 23 & 24, 2020 |
|
5 |
Configuration, configurational isomers with asymmetric centre(s) (enantiomers, diastereomers, epimers etc.) |
November 30, 2020 |
|
December 1, 2020 |
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|
6 |
Configurational isomers with axis of chirality like atropisomers (biphenyls, terphenyls, allens, spiranes etc.) and plane of chirality |
December 7, 2020 |
|
December 8, 2020 |
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|
7 |
Stereoselectivity vs. stereospecificity |
December 14, 2020 |
|
Stereochemical outcome of addition (C=C, C≡C, C=X where X = O, S, NR) reactions |
December 15, 2020 |
|
|
8 |
Mid-Term Examination (December 28 2020 to January 1, 2021) |
|
|
9 |
Stereochemical outcome of elimination reactions |
January 4 & 5, 2021 |
|
10 |
Stereochemical outcome of substitution reactions |
January 11, 2021 |
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January 12, 2021 |
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|
12 |
Stereochemical outcome of pericyclic reactions & molecular rearrangements |
January 18, 2021 |
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January 19, 2021 |
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13 |
Asymmetric synthesis including chiral pool approach |
January 25, 2021 |
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January 26, 2021 |
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|
14 |
Asymmetric synthesis involving chiral substrates and chiral reagents |
February 1, 2021 |
|
February 2, 2021 |
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|
15 |
Asymmetric catalysis |
February 8, 2021 |
|
February 9, 2021 |
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|
16 |
Felkin Anh’s Model |
February 15 & 16, 2021 |
|
17 |
Resolution of Racemic modifications |
February 22 & 23, 2021 |
|
18 |
Final Examination (March 1-5, 2021) |
|
Note: You can reserve one week for sessional or mid-term exam, and, if you wish, one week for student presentations of the assigned research project
RESEARCH PROJECT
Presentation on different current topics in due course after mid term examination on Fridays as per time table.
ASSESSMENT CRITERIA
Mid Term Examination: 30% (100% objective type)
Sessional: 20% (Attendance = 10%, Assignments = 5%, Presentation / conduct = 5%)
Presentation: 5% (included in sessional marks)
Participation: 5% (included in sessional marks)
Final examination: 50% (60% subjective type; 40% objective; premid :postmid course = 3:7)
RULES AND REGULATIONS
Minimum attendance required for sitting in Mid/Final Exam. = 75%
Course Material
- Total Lessons 1
- Department Chemistry
- About Visit Profile
-
Teacher
Prof Dr Abdul Rauf Raza
