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2017　Advanced Organic Chemistry I (Organic Reactions)

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Academic unit or major
Undergraduate major in Chemical Science and Engineering
Instructor(s)
Tanaka Ken 
Class Format
Lecture     
Media-enhanced courses
Day/Period(Room No.)
Mon3-4(S421)  
Group
-
Course number
CAP.A231
Credits
1
Academic year
2017
Offered quarter
4Q
Syllabus updated
2017/3/17
Lecture notes updated
2017/11/24
Language used
Japanese
Access Index

Course description and aims

[Summary of the lecture] In this lecture, classification of organic reactions based on the reaction mechanism and systematical explanation of them will be presented 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 lecture]
To understand the variety of organic synthesis reactions based on not the starting materials but the reaction mechanism is important in order to understand the reactions. In this lecture, pericyclic reaction, functional group transformation reaction, aromatic electrophilic substitution reaction, the reaction of carbanion, and stereoselective reaction / stereospecific reaction, will be understood. In addition, develop the ability to discuss about reactions based on the knowledge.

Student learning outcomes

By course of this lecture, to acquire the following capabilities.
(1) Ability to understand the classification of the reaction based on the reaction mechanism.
(2) Ability to understand pericyclic reaction.
(3) Ability to understood with functional group transformation reaction.
(4) Ability to understand the aromatic electrophilic substitution reaction.
(5) Ability to understand the reaction of the carbanion.
(6) Ability to understand the rearrangement reaction.
(7) Ability to understand stereoselective reaction / stereospecific reaction.

Keywords

pericyclic reaction, oxidation, reduction, Friedel-Crafts reaction, orientation, enolate, carboyl groups, Michael addition、Claisen rearrangement、Wittig rearrangement

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) pericyclic reaction, (2) functional group conversion reaction, (3) aromatic electrophilic substitution reaction, (4) preparation of carbanions, (5) alkylation / aldol reaction / acylation reaction, (6 ) 1,4-addition, (7) rearrangement.
In addition, each lecture involves proctice at the last session. 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 pericyclic reaction and practice Explain pericyclic reaction based on the reaction mechanism.
Class 2 functional group transfer reaction and practice Explain functional group transfer reaction based on the reaction mechanism.
Class 3 aromatic electrophilic substitution reaction and practice Explain aromatic electrophilic substitution based on the reaction mechanism.
Class 4 preparation of carbanions and practice Explain preparation of carbanions.
Class 5 alkylation / aldol reaction / acylation reaction and practice Explain alkylation / aldol reaction / acylation reaction based on the reaction mechanism.
Class 6 1,4-addition and practice Explain 1,4-addition based on the reaction mechanism.
Class 7 rearrangement and practice Explain rearrangement based on the reaction mechanism.
Class 8 Practice problems and interpretation for confirming the level of understanding Solve practice problems by accurate understanding of the above all lectures.

Textbook(s)

McMurry Organic Chemistry, international edition of 8th 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)
  • CAP.B315 ： Organic Chemistry V (Carbonyl Compounds)
  • CAP.B316 ： Organic Chemistry VI (Amines)
  • CAP.A332 ： Advanced Organic Chemistry II (Organic Reactions)
  • CAP.A333 ： Advanced Organic Chemistry III (Structure and Function)
  • CAP.A334 ： Advanced Organic Chemistry IV (Organic Synthesis)
  • CAP.A335 ： Advanced Organic Chemistry V (Drug Design and Synthesis)

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), and Organic Chemistry III (Aromatic Compounds).

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

ktanaka[at]apc.titech.ac.jp

Office hours

Make a reservation by an e-mail in advance.

Other

Attention on studying will be explained in the first lecture. Please judge whether to take course based on it.

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