[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.
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
|✔ Specialist skills||Intercultural skills||Communication skills||Critical thinking skills||✔ Practical and/or problem-solving skills|
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|
|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.|
McMurry Organic Chemistry, international edition of 9th revised edition (Cengage Learning) ISBN: 9784807909124
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th edition (Cengage Learning) ISBN: 9784807909155
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.)
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).
ito.s.ao[at]m.titech.ac.jp （Shigekazu Ito)
otsuka[at]polymer.titech.ac.jp (Hideyuki Otsuka）
Make a reservation by an e-mail in advance.