The course is designed to understand pericyclic reactions such as electrocyclization, cycloaddition reaction, and sigmatropic rearrangement based on frontier orbital theory and Woodward-Hoffmann rule. This course also focuses on stereo-electronic effects to understand general reactivity of organic compounds and stereo-selectivity in organic reactions.
Students will able to explain basic facts related to the stereochemistry of organic compounds and the stereoselectivity of reactions such as the stereoelectronic effect and molecular orbital theory. Students will also gain an understanding of the basics and applications of the Woodward-Hoffmann rules and frontier orbital theory.
Pericyclic reaction, Electrocyclization, Cycloaddition reaction, Sigmatropic rearrangement, Frontier orbital theory, Woodward-Hoffmann rule.
Intercultural skills | Communication skills | Specialist skills | Critical thinking skills | Practical and/or problem-solving skills |
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Most course contents and topics are given by board writing.
Course schedule | Required learning | |
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Class 1 | Stereoelectronic effects: Felkin–Anh model, Cieplak model, Bürgi–Dunitz trajectory | Exercise problems might be given in this class. |
Class 2 | Stereoelectronic effects: conformation and reactivity of cyclohexane derivative, A-value | Exercise problems might be given in this class. |
Class 3 | Stereoelectronic effects: anomeric effect | Exercise problems might be given in this class. |
Class 4 | Stereoelectronic effects: Gauche effect | Exercise problems might be given in this class. |
Class 5 | Stereoelectronic effects: Baldwin's rule | Exercise problems might be given in this class. |
Class 6 | Stereoelectronic effects: Bredt rule, reaction of small ring-sized compounds | Exercise problems might be given in this class. |
Class 7 | Stereoelectronic effects: other topics and exercise problems | Exercise problems might be given in this class. |
Class 8 | Woodward-Hoffmann rule and frontier orbital theory | Exercise problems might be given in this class. |
Class 9 | Electrocyclization-4p and 6p electrocyclizations | Exercise problems might be given in this class. |
Class 10 | Electrocyclization-ionic reactions | Exercise problems might be given in this class. |
Class 11 | Cycloaddition reaction-basic principles | Exercise problems might be given in this class. |
Class 12 | Cycloaddition reaction-examples | Exercise problems might be given in this class. |
Class 13 | Sigmatropic rearrangement-[1,n] sigmatropic rearrangement | Exercise problems might be given in this class. |
Class 14 | Sigmatropic rearrangement-[m,n] sigmatropic rearrangement | Exercise problems might be given in this class. |
Class 15 | Summary | Exercise problems might be given in this class. |
None
For stereoelectronic effects
1) Stereoelectronic Effects, A. J. Kirby, Oxford University Press; 2) Stereochemistry in Organic Compounds, E. L. Eliel and S. H. Wilen, Wiley;
For pericyclic reactions
3) Pericyclic Reactions, I. Fleming, Oxford University Press.
"Final exam. Students' understanding of stereoelectronic effects and pericyclic reactions and their ability to apply them to problems will be assessed. "
Have basic knowledge of organic chemistry