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2017　Basic Concepts of Organic Chemistry

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Academic unit or major
Graduate major in Chemistry
Instructor(s)
Iwasawa Nobuharu  Ohmori Ken 
Class Format
Lecture     
Media-enhanced courses
Day/Period(Room No.)
Mon3-4(H112)  Thr3-4(W621)  
Group
-
Course number
CHM.D401
Credits
2
Academic year
2017
Offered quarter
1Q
Syllabus updated
2017/3/17
Lecture notes updated
-
Language used
Japanese
Access Index

Course description and aims

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.

Student learning outcomes

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.

Keywords

Pericyclic reaction, Electrocyclization, Cycloaddition reaction, Sigmatropic rearrangement, Frontier orbital theory, Woodward-Hoffmann rule.

Competencies that will be developed

✔ Specialist skills Intercultural skills Communication skills Critical thinking skills Practical and/or problem-solving skills

Class flow

Most course contents and topics are given by board writing.

Course schedule/Required learning

  Course schedule Required learning
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.

Textbook(s)

None

Reference books, course materials, etc.

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.

Assessment criteria and methods

"Final exam. Students' understanding of stereoelectronic effects and pericyclic reactions and their ability to apply them to problems will be assessed. "

Related courses

  • CHM.D201 ： Organic Chemistry I
  • CHM.D202 ： Organic Chemistry II
  • CHM.D301 ： Organic Chemistry III
  • CHM.D331 ： Organic Synthesis
  • CHM.D333 ： Organic Reactions

Prerequisites (i.e., required knowledge, skills, courses, etc.)

Have basic knowledge of organic chemistry

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