山口大学教務システム - 1061330890-応用化学実験Ⅲ

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
前期	木5～10	実験・実習	10.0
時間割番号	科目名[英文名]			使用言語	単位数
1061330890	応用化学実験Ⅲ[Applied Chemistry Laboratory Ⅲ]			日本語	2
担当教員（責任）[ローマ字表記]					メディア授業
山吹一大[YAMABUKI Kazuhiro]					ー
担当教員[ローマ字表記]
山吹一大　[YAMABUKI Kazuhiro], 鬼村謙二郎　[ONIMURA Kenjiro], 岡本浩明　[OKAMOTO Hiroaki], 西形孝司　[NISHIKATA Takashi], 川本拓治　[KAWAMOTO Takuji], （未　定）
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

Acquire basic operations related to organic synthesis/analysis and polymer synthesis/analysis through chemical experiments conducted by instructors who specialize in organic chemistry and polymer chemistry, and deepen understanding of organic chemistry and polymer chemistry learned in lectures. for the purpose.

授業の到達目標

1. Gain a clear understanding of the experimental content, the reactions occurring, and the significance of the experimental procedures.
2. Understand the potential hazards in organic experiments and acquire proper experimental techniques.
3. Understand the meaning behind the handling of experimental equipment and make appropriate judgments regarding experimental procedures.
4. Develop the ability to recognize and respond to potential hazards in organic experiments.
5. Cultivate an active interest in and curiosity about the experimental content, and engage proactively in experiments.
6. Actively and appropriately record experimental procedures and results during experiments.
7. Conduct experiments with safety in mind (appropriate attire and experimental techniques).
8. Perform experimental procedures correctly.
9. Present and explain experimental results logically.

授業計画

【全体】

・Multiple faculty members will be in charge of this experiment, and they will conduct experiments related to organic chemistry.
・In the first half, basic operations necessary for organic chemistry experiments will be performed.
・In the second half, we will actually carry out the organic reaction (polymerization reaction) that we learned in lectures related to organic chemistry, and have them perform a comprehensive understanding of knowledge and technology.
・In some cases, not all groups will conduct the same experiment at the same time. Also, the themes of experiments are not necessarily conducted in the order of the syllabus. Please check the schedule of the experiment you are in charge of in advance.
・We will contact you at the time of the first guidance or at a later date regarding the division into groups and the order of implementation themes.

	項目	内容	授業時間外学習	備考

第1回	Guidance on precautions related to experiments in organic synthesis chemistry and polymer synthesis chemistry, as well as confirmation of laboratory safety protocols.	You are required to attend as we will explain the overview of the experiments, important points for report writing and submission, and safety precautions. Key Words: Safety guidelines in the laboratory, handling of reagents, guidance for each experiment.	Study the section on chemical handling and the Department of Applied Chemistry in the reference book "Safety Guidelines for Experiments and Practical Training." (Estimated study time: 4 hours)

第2回

Basic Operations in Organic Synthesis (1)

Basic Operations in Organic Chemistry Experiments: Extraction, Distillation, Thin Layer Chromatography (TLC)

Summarize the key points for extraction, distillation, and thin layer chromatography (TLC) in your report. Since experiments will vary by group, be sure to pay attention to the notices. (Estimated study time: 4 hours)

第3回

Basic Operations in Organic Synthesis (2)

Basic Operations in Organic Chemistry Experiments: Filtration, Recrystallization, Melting Point Measurement

Summarize the key points for filtration, recrystallization, and melting point measurement in your report. Since experiments will vary by group, be sure to pay attention to the notices. (Estimated study time: 4 hours)

第4回

Basic Operations in Organic Synthesis (3)

Thin Layer Chromatography (TLC)

Summarize the key points for performing thin layer chromatography (TLC) in your report. (Estimated study time: 4 hours)

第5回

Thiamine catalyzed Benzoin Condensation

Synthesize benzoin through the benzoin condensation of an aldehyde. The synthesized benzoin will be used in next week's reaction. Additionally, learn how to use thin layer chromatography (TLC).

Carefully read the English textbook instructions, prepare your experiment notebook, and submit a copy by the day before the experiment. Be sure to create a thorough report after the experiment. (Estimated study time: 4 hours)

第6回

1. Nitric Acid Oxidation of Benzoin Derivatives yielding Benzil 2.Borohydride Reduction of Benzil derivatives

Synthesize benzoin through the benzoin condensation of an aldehyde. The synthesized benzoin will be used in next week's reaction. Additionally, learn how to use thin layer chromatography (TLC).

第7回

1. Griess Reaction 2. Suzuki-Miyaura Cross-Coupling Reaction

Learn a two-step reaction. Synthesize an iodide from an aniline derivative, and then use the synthesized iodide in a Pd-catalyzed cross-coupling reaction.

第8回

Synthesize dibenzalacetone through an aldol condensation reaction

Learn the general experimental procedures required for the synthesis of dibenzalacetone through aldol condensation, including filtration and melting point measurement techniques, as well as the hazards associated with the reagents used. Additionally, synthesize dibenzalacetone through the aldol condensation of benzaldehyde and acetone, and perform purification by recrystallization.

Understand the content of the textbook and the experimental procedures. Memorize the sequence of experimental operations. Research the Material Safety Data Sheet (MSDS) for the intermediate diazonium salt, as well as the melting point, color, and shape of the target compound. (Estimated study time: 4 hours)

第9回

Synthesis of acetylsalicylic acid (aspirin).

Learn the general experimental procedures required for the synthesis of aspirin, as well as the hazards associated with the reagents used. Synthesize the crude product of aspirin through the reaction between salicylic acid and acetic anhydride, and perform purification by recrystallization. Measure the melting point of the obtained product.

Understand the content of the textbook and the experimental procedures. Memorize the sequence of experimental operations. Research the Material Safety Data Sheet (MSDS) for the intermediate diazonium salt and investigate the melting point, color, and shape of the target compound. (Estimated study time: 4 hours)

第10回

Chemical Reaction Search and Investigation

Learn how to investigate original research papers and utilize chemical databases such as SciFinder. Use these tools to plan the synthesis of compounds.

Prepare in advance and create the report. (Estimated study time: 4 hours)

第11回

Diels-Alder reaction

Synthesize complex compounds using the Diels-Alder reaction.

Carefully translate the English textbook and fully understand the experimental procedures. Prepare your experiment notebook and submit it by the day before the experiment. Be sure to create a thorough report after the experiment. Additionally, research the properties of the organic compounds you will handle using the Material Safety Data Sheets (MSDS). (Estimated study time: 4 hours)

Carefully translate the English textbook and fully understand the experimental procedures. Prepare your experiment notebook and submit it by the day before the experiment. Be sure to create a thorough report after the experiment. Additionally, research the properties of the organic compounds you will handle using the Material Safety Data Sheets (MSDS). (Estimated study time: 4 hours)

第12回

Co-polymerization of styrene and methyl methacrylate.

Synthesize a polymer through radical co-polymerization using styrene and methyl methacrylate, which are general-purpose vinyl monomers.

Understand the content of the textbook and the experimental procedures. Follow the precautions in the textbook and calculate the amounts of styrene and methyl methacrylate to be used. (Estimated study time: 4 hours)

第13回

Emulsion polymerization of vinyl acetate.

Perform the emulsion polymerization of vinyl acetate using sodium lauryl sulfate as an emulsifier and azobisisobutyronitrile (AIBN) as a radical initiator. Additionally, learn the purification methods for the polymer.

Understand the content of the textbook and the experimental procedures. Memorize the sequence of experimental operations. Also, carefully read the section on glassware. (Estimated study time: 4 hours)

第14回

Gas chromatography (GC)

Learn the principles and operational methods of various chromatography techniques used in organic synthesis and analytical chemistry, and understand how to create calibration curves necessary for the quantitative analysis of organic compounds.

Read the section on gas chromatography in the textbook and reference books. (Study time: 4 hours)

第15回

Report submission

Review and revise the returned report.

Review and revise the report (Study time: 4 hours).

※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: 30%　B: 10%　C: 60%　D: --%

成績評価法

Evaluation will be based on the reports for each experiment. (100% based on reports)

教科書にかかわる情報

備考

Basic Organic Chemistry & Polymer Chemistry Experiments
Hiroshi Tsutsumi, Kenjiro Onimura, Takashi Nishigata, Hiroaki Okamoto, Takuji Kawamoto, Kazuto Yamabuki, Shiho Yamato, co-authored; Kodama Printing; 2025.

参考書にかかわる情報

備考

Guide to Safety in Experiments and Practical Training, Safety and Health Committee, Faculty of Engineering, Yamaguchi University,

* Reference book notes
The above reference books are not required to be purchased, but they will be helpful when conducting experiments and writing reports. Please also refer to organic chemistry and polymer chemistry textbooks in libraries.

メッセージ

Many organic reagents are dangerous, so be sure to bring a white coat and safety glasses and wear them in the laboratory. If you have long hair, tie it up so that you are not in danger. In addition, be prepared to conduct experiments safely (sandals, clogs, shoes with poor stability, etc. are strictly prohibited). Do not eat or drink in the laboratory.
If you are not ready to wear clothes that allow you to conduct experiments safely, you will be prohibited from conducting experiments.

キーワード

Organic Chemistry, Polymer Chemistry, Synthetic Experiments, Organic Chemicals, Safety, Experimental Procedures, Nucleophilic Substitution Reaction, Electrophilic Addition Reaction, Diazotization Reaction, Sandmeyer Reaction, Aldol Reaction, Reduction Reaction, Radical Polymerization, Emulsion Polymerization, Copolymerization, benzoin condensation, cross-coupling

持続可能な開発目標（SDGs）

(水・衛生)すべての人々の水と衛生の利用可能性と持続可能な管理を確保する。

(エネルギー)すべての人々の、安価かつ信頼できる持続可能な近代的エネルギーへのアクセスを確保する。

(持続可能な生産と消費)持続可能な生産消費形態を確保する。

(気候変動)気候変動及びその影響を軽減するための緊急対策を講じる。

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メディア授業