2020 Organic Chemistry IV (Nucleophilic Substitution) B

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Academic unit or major
Undergraduate major in Chemical Science and Engineering
Ito Shigekazu 
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Course description and aims

[Summary of the course] In this course, stereochemistry in the tetrahedron center, synthesis and reactions of organic halides, and
nucleophilic substitution and elimination reactions of the alkyl halides will be explained for the students who studied Organic Chemistry I
(Alkanes) (Chemical Science and Engineering), Organic Chemistry II (Alkenes), and Organic Chemistry III (Aromatic Compounds).
[Aim of the course] The stereochemistry in the tetrahedron center is important in understanding biochemistry as well as organic
chemistry, and is essential to understand the reaction mechanism of various organic compounds. Students understand phenomena of
isomerism such as origin of antipode and optical activity of molecules, and then they understand chemistry of the organic halide. Finally,
students acquire the ability to discuss the mechanism of the most basic organic reactions, especially nucleophilic substitution reactions,
using stereochemical knowledge.

Student learning outcomes

By the end of this course, students acquire the following abilities:
(1) Ability to understand basic knowledge and way of thinking about stereochemistry that is the important characteristic of organic
(2) Ability to explain nucleophilic substitution reactions, that is a basic reaction in organic chemistry, using stereochemical knowledge and
way of thinking.
(3) Ability to discuss the reaction mechanism, based on (1) and (2) above.
(4) Ability to draw up a synthetic plan of a target compound, based on (1) and (2) above.


Enantiomers, optical activity, phenomena of isomerism, alkyl halides, organometallic chemistry, nucleophilic substitution reactions, SN2
reactions, SN1 reactions, elimination reactions

Competencies that will be developed

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

Class flow

This course will proceed in the following order: (1) stereochemistry in the tetrahedron center, (2) property, synthesis, and reactions of
organic halides, (3) reactions of alkyl halides (nucleophilic substitution and elimination reactions). In the last day, practice problems and
interpretation of them will be provided to check the level of understanding.

Course schedule/Required learning

  Course schedule Required learning
Class 1 Enantiomer and optical activity Explain an enantiomer and optical activity.
Class 2 Phenomena of isomerism Explain phenomena of isomerism.
Class 3 Synthesis of alkyl halides Explain synthesis of alkyl halides.
Class 4 Reactions of alkyl halides, introduction of organometallic chemistry Explain reactions of alkyl halides and introduction of organometallic chemistry.
Class 5 SN2 reactions Explain SN2 reactions.
Class 6 SN1 reactions Explain SN1 reactions.
Class 7 Comparison between elimination reaction, nucleophilic substitution and elimination Discuss the reaction mechanism and draw up the synthetic plan of the target compound, based on accurate understanding of the mechanism of nucleophilic substitution and elimination reactions.

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 9th revised edition (Cengage Learning) ISBN: 9784807909124

Reference books, course materials, etc.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th edition (Cengage Learning) ISBN: 9784807909155

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.A231 : Advanced Organic Chemistry I (Organic Reactions)
  • CAP.A332 : Advanced Organic Chemistry II (Organic Reactions)

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), Organic Chemistry II (Alkenes), and Organic Chemistry III (Aromatic Compounds).

Contact information (e-mail and phone)    Notice : Please replace from "[at]" to "@"(half-width character).

ito.s.ao[at]m.titech.ac.jp (Shigekazu Ito)
otsuka[at]polymer.titech.ac.jp (Hideyuki Otsuka)

Office hours

Make a reservation by an e-mail in advance.

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