Course Title : Organic Chemistry III (Fundamental Chemistry)

Code 72140
Course Year 3rd year
Term
Class day & Period
Location
Credits 2
Restriction No Restriction
Lecture Form(s) Lecture
Language Japanese
Instructor Tsuji, Kondo, Ohmura,

Course Description

The lecture is given on Organic Chemistry which is indispensable to a researcher and an engineer. After the Organic Chemistry I (2nd year, 2nd term) and the Organic Chemistry II (3rd year, 1st term), the lecture is given on the chapters 22 - 26 of the same textbook, which covers characteristic reactions of electron-deficient alkenes and aromatic compounds, protection and deprotection of functional groups, and chemistry of carbonyl compounds including various reactivity of enolates.

Grading

The grade is given based on the final examination.
Attendance and reports during the class could be considered.

Course Goals

Comprehensive understanding of reactions of aromatic compounds, reactivities of functional groups, and chemistry of carbonyl compounds including alkylation of enolates, the aldol reaction, and other condensation reactions is a goal of this course. By combining ideas learned in the Organic Chemistry I and the Organic Chemistry II, high-level knowledge of organic chemistry must be acquired which is indispensable for a accomplished researcher and engineer.

Course Topics

Theme Class number of times Description
Conjugate addition and nucleophilic aromatic substitution 3 Conjugate addition reactions, conjugate substitution reactions, nucleophilic epoxidation, electrophilic aromatic substitution, addition-elimination mechanism, diazonium compounds, reactions via benzyne intermediate (Chapter 22)
Chemoselectivity and protecting groups 3 Reducing agents, reduction of carbonyl groups, catalytic hydrogenation, removal of functional groups, dissolving metal reductions, selectivity in oxidation reactions, reactivities of functional groups, protecting groups (Chapter 23)
Regioselectivity 2 Regioselectivity in electrophilic aromatic substitution reactions, electrophilic attack on alkenes, regioselectivity in radical reactions, nucleophilic attack on allylic compounds, electrophilic attack on conjugated dienes, direct addition vs. conjugate addition (Chapter 24)
Alkylation of enolates 3 Alkylation of nitriles and nitroalkanes, electrophiles for alkylation, alkylation of lithium enolates, alkylation using enolate equivalents, alkylation of beta-dicarbonyl compounds, regioselectivity in alkylation of ketones (Chapter 25)
Reactions of enolates with carbonyl compounds: the aldol and Claisen reactions 3 The aldol reaction, cross aldol condensation, aldol reactions using enolates and their equivalents, intramolecular aldol reaction, acylation of enolates, Claisen condensation, cross Claisen condensation, intramolecular cross Claisen condensation (Chapter 26)
1
1

Textbook

Organic Chemistry Second Edition (J. Clayden, N. Greeves, S. Warren, Oxford University Press, 2012)

Textbook(supplemental)

マクマリー 有機化学 -生体反応へのアプローチ(マクマリー著;柴﨑正勝,岩澤伸治,大和田智彦,増野匡彦 監訳;東京化学同人, 2009)

Prerequisite(s)

Basic Organic Chemistry A, Basic Organic Chemistry B, Organic Chemistry I(Fundamental Chemistry), Organic Chemistry II(Fundamental Chemistry)

Web Sites

Additional Information

Two classes are lectured at the same time.