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開講年度 開講学部等
2025 工学部
開講学期 曜日時限 授業形態 AL（アクティブ・ラーニング）ポイント
後期 水5～6 講義  
時間割番号 科目名[英文名] 使用言語 単位数
1062330370 有機反応化学[Organic Reaction Chemistry] 日本語 2
担当教員（責任）[ローマ字表記] メディア授業
川本 拓治[KAWAMOTO Takuji] ー
担当教員[ローマ字表記]
川本 拓治　[KAWAMOTO Takuji]
特定科目区分   対象学生   対象年次 3～
ディプロマ・ポリシーに関わる項目 カリキュラムマップ(授業科目とDPとの対応関係はこちらから閲覧できます)
授業の目的と概要
This is a class for organic reaction mechanism based on organic electronic theory.
授業の到達目標
Organic reactions organized by mechanistic classification
Explain the reaction mechanism of simple organic reactions using organic electron theory
Organize the properties of each functional group
Explain reactions in complex compounds
授業計画
【全体】
This lecture progresses showing representative reaction mechanism such as substitution, addition, elimination, and rearrangements. This will help for your understanding how the organic reactions progress.
項目 内容 授業時間外学習 備考
第1回 Preparation for studying organic reaction mechanism
Shapes of organic molecules and hybrid orbitals, polarity of chemical bonds, resonance effects, steric effects, reaction pathway, intermediates, transition state 		Please spend at least two hours preparing for the relevant sections of the textbook.
第2回
Acids and bases
Definition of acids and bases, pKa, acidity of carboxylic acids, acidity of alcohols and phenols, acidity of other organic acids, basicity of organic bases 		Please spend at least two hours preparing for the relevant sections of the textbook.
第3回 Nucleophilic substitution reactions
Outline of SN2 reactions, outline of SN1 reactions, comparison of the two reactions, Steric effects, Effects by leaving groups, solvent effects, intramolecular nucleophilic substitution reactions 		Please spend at least two hours preparing for the relevant sections of the textbook.
第4回
Elimination reactions
Outline of E2 reactions, stereochemistry of the elimination, regiochemistry of the elimination, outline of E1 reactions, outline of E1CB reactions, comparison of the three reactions, Comparison of SN2 and E2 reactions, intramolecular elimination reactions, alpha-elimination, gamma-elimination 		Please spend at least two hours preparing for the relevant sections of the textbook.
第5回 Electrophilic addition to carbon-carbon double and triple bonds
Addition of halogen to carbon-carbon double bonds, addition of hydrobromic acid to carbon-carbon double bonds, stabilization of carbocations, Hammond postulate, addition od water to carbon-carbon double bonds (hydration reactions) 		Please spend at least two hours preparing for the relevant sections of the textbook.
第6回
Rearrangement reactions
Rearrangement of carbocations, Pinacole rearrangement, Wagner-Meerwein rearrangement, Beckmann rearrangement, Benzilic acid rearrangement, rearrangement of nitrene and carbene, Baeyer-Villiger reaction 		Please spend at least two hours preparing for the relevant sections of the textbook.
第7回
Nucleophilic addition to carbonyl groups: 1 		Tow important aspects of carbonyl groups, nucleophilic addition to carbonyl groups, addition reaction with dehydration Please spend at least two hours preparing for the relevant sections of the textbook.
第8回
Nucleophilic addition to carbonyl groups: 2
ALdol and related reactions, hydrolysis of esters, Michael addition reaction, Wittig reaction 		Please spend at least two hours preparing for the relevant sections of the textbook.
第9回 Aromaticity and electrophilic aromatic substitution reactions
Stabilization by aromaticity, analysis of pi orbitals in benzene by Huckel molecular orbital theory, aromaticity, nitration of benzene, electrophilic aromatic substitution reactions, regiochemistry of the SEAr reactions 		Please spend at least two hours preparing for the relevant sections of the textbook.
第10回
mid-term exam
all materials before this time will be included 		Please spend at least two hours preparing for the relevant sections of the textbook.
第11回
Nucleophilic aromatic substitution reactions
Nucleophilic aromatic substitution reactions, Ulmann coupling reaction, Sandmyere reaction, benzyne, definition of Hammett sigma values, ro values in Hammett plots, ortho effect 		Please spend at least two hours preparing for the relevant sections of the textbook.
第12回
Woodward-Hoffmann's rule
Concerted reactions, phase of orbitals, electrocyclic reactions, cycloaddition reactions, 1,n-hydrogen transfer reactions, Claisen rearrangement 		Please spend at least two hours preparing for the relevant sections of the textbook.
第13回
Radical reactions
Carbon radicals, stability and reactivity, radical chain reaction mechanism, tin radicals 		Please spend at least two hours preparing for the relevant sections of the textbook.
第14回
Radical reactions
Carbon radicals, stability and reactivity, radical chain reaction mechanism, tin radicals 		Please spend at least two hours preparing for the relevant sections of the textbook.
第15回
Photo reactions
Photo-excitation of molecules, fluorescence and phosphorescence, photo-cyclization reactions, photo-degradation reactions 		Please spend at least two hours preparing for the relevant sections of the textbook.
第16回
Final exam. 		All materials will be included in the exam Please spend at least two hours preparing for the relevant sections of the textbook.
※AL（アクティブ・ラーニング）欄に関する注
・授業全体で、AL（アクティブ・ラーニング）が占める時間の割合を、それぞれの項目ごとに示しています。
・A〜Dのアルファベットは、以下の学修形態を指しています。
【A：グループワーク】、【B：ディスカッション・ディベート】、【C：フィールドワーク（実験・実習、演習を含む）】、【D：プレゼンテーション】
A: --%　B: --%　C: --%　D: --%
成績評価法
Evaluation will be based on quizzes and a written test at the end of the semester.
(Quiz: 5%, written test at the end of the semester: 95%)
If attendance is less than 70%, the student will be disqualified.
教科書にかかわる情報
教科書 書名 Organic chemistry : a mechanistic approach ISBN 9780199693276
著者名 Tadashi Okuyama, Howard Maskill 出版社 Oxford University Press 出版年 2014
備考
参考書にかかわる情報
参考書 書名 有機合成化学 ISBN 9784807907601
著者名 檜山為次郎, 大嶌幸一郎編著 ; 丸岡啓二 [ほか] 著 出版社 東京化学同人 出版年 2012
参考書 書名 ボルハルト・ショアー現代有機化学問題の解き方 ISBN 9784759820317
著者名 N.E. Schore [著] ; 大嶌幸一郎 [ほか] 訳 出版社 化学同人 出版年 2020
参考書 書名 有機ラジカル反応の基礎　改訂2版 ISBN 9784621310700
著者名 柳日馨,川本拓治,柳日馨 著・文・その他,川本拓治 著・文・その他 出版社 出版年
参考書 書名 有機反応機構 : 酸・塩基からのアプローチ ISBN 9784807909681
著者名 奥山格著 出版社 東京化学同人 出版年 2020
参考書 書名 ボルハルト・ショアー現代有機化学 ISBN 9784759820294
著者名 K.P.C. Vollhardt, N.E. Schore [著] ; 大嶌幸一郎 [ほか] 訳 出版社 化学同人 出版年 2019
備考
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関連科目
履修条件
連絡先
tak102★yamaguchi-u.ac.jp
（★は@に置き換えてください。）
オフィスアワー
I will accept students anytime during class days (from 9:00 a.m. to 5:00 p.m., excluding holidays and substitute holidays, but excluding times when I am away on business or teaching in Yamaguchi) during the semester until the end of the examinations. However, please make an appointment in advance by e-mail.
If you have any questions or comments, please send them from the university address.
Emails from personal private addresses will be classified as junk mail.
Also, please understand the minimum rules of e-mail before sending.

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