2022 Advanced Organic Chemistry I (Organic Reactions)

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Academic unit or major
Undergraduate major in Chemical Science and Engineering
Tanaka Katsunori 
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Course description and aims

[Summary of the lecture] In this lecture, carbon skeletons of organic compounds will be focused in view of their variations. Characteristics of functional groups will also be taught. The synthetic methods for the construction of carbon skeletons will be emphasized as the key in organic synthesis.
[Aim of the lecture] Students understand the mechanism for stereoselective organic reactions and the reported synthesis of complex organic compounds, such as natural products. Students acquire the ability to propose the synthetic plan for the synthesis of complex organic molecules.

Student learning outcomes

By the end of this course, students acquire the following ability:
(1) Explain characteristic features of functional groups, which are necessary for drawing up the synthetic plan.
(2) Explain the mechanism and origin for chemoselectivity, regioselectivity, and stereoselectivity of the reactions.
(3) Draw up the multi-step synthetic plan of the complex organic compounds.


Synthesis, retro-synthesis, carbon-carbon bond formation, functional group interconversion, functional group transposition, stereoselectivity, chemoselectivity, regioselectivity, common atoms, linear/convergent syntheses, symmetry, key intermediates

Competencies that will be developed

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

Class flow

This lecture will proceed in the following order: (1) synthesis, retro-synthesis, (2) CCF (Carbon-Carbon Bond Formation), FGI (Functional Group Interconversion), FGT (Functional Group Transposition), selectivity, (3) linear/convergent syntheses, symmetry of target molecules, synthetic intermediate and common atom. In the last day, practice problems and interpretation of them will be carried out to confirm the level of understanding.

Course schedule/Required learning

  Course schedule Required learning
Class 1 Introduction Explain the importance of organic syntheses.
Class 2 Complexity in carbon skeletons in target molecules Analyze complexity in carbon skeletons.
Class 3 Characteristic functional groups and chemoselectivity thereof Explain characteristics in functional groups and chemoselectivities.
Class 4 CCF: Carbon-Carbon Bond Formation Explain synthesis of carbon skeletons.
Class 5 Stereoselectivity: origin and control Explain origins and control of stereoselectivity.
Class 6 Multi-step syntheses Draw up the multi-step synthetic plan of the target compound.
Class 7 Practice problems and interpretation for confirming the level of understanding Discuss the reaction mechanism and draw up the synthetic plan of the target molecules.

Out-of-Class Study Time (Preparation and Review)

To enhance effective learning, students are encouraged to spend approximately 100 minutes preparing for class and another 100 minutes reviewing class content afterwards (including assignments) for each class.
They should do so by referring to textbooks and other course material.


McMurry Organic Chemistry, international edition of 8th or 9th revised edition (Cengage Learning) ISBN-13: 978-0840054531

Reference books, course materials, etc.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 8th edition (Cengage Learning) ISBN-13: 978-0840054456

Assessment criteria and methods

Practice problems and interpretation for confirming the level of understanding (85%), level of class participation (15%) (The level of class participation will be calculated by discussion, small examination and so on in the lecture.)

Related courses

  • CAP.B211 : Organic Chemistry I (Alkanes) (Chemical Science and Engineering)
  • CAP.B212 : Organic Chemistry II (Alkenes)
  • CAP.B213 : Organic Chemistry III (Aromatic Compounds)
  • CAP.B214 : Organic Chemistry IV (Nucleophilic Substitution)

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

The condition of the study will not be made, but it is desirable to study Organic Chemistry I (Alkanes) (Chemical Science and Engineering), Organic Chemistry II (Alkenes), Organic Chemistry III (Aromatic Compounds), and Organic Chemistry IV (nucleophilic substitution).

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