柑橘小夜曲本科生实验室亚胺缩合反应的改进程序

IF 2.9 3区 教育学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Vivian T. Lee, Jordan Kellenberger, Katherine Borton and Shawn D. Montag*, 
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引用次数: 0

摘要

亚胺缩合反应是第二学期有机化学课堂上的常见内容。随着近年来对绿色化学和开发更安全反应的推动,人们对尝试在水或水性溶剂存在下进行有机反应的兴趣日益浓厚。本文讨论的工作是对之前报告的实验室实验的重要更新,该实验利用鲜榨果汁和水作为反应溶剂,比较亚胺缩合反应的反应性与立体效应、电子效应和 pH 值的关系。五种不同的芳香族苯甲醛衍生物与正丁胺、仲丁胺和叔丁胺在水溶剂存在下发生反应。多个小组的学生成功地完成了更新的反应,并用 1H NMR 光谱分析了产物,计算了每个反应的转化率,分析了反应趋势。这个亚胺缩合实验室实验的转化率大大超过了我们之前报告的使用有机溶剂的研究(J. Chem.2023, 100 (11), 4456)。本文介绍了实施这一最新亚胺缩合项目的策略。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
A Citrus Serenade: An Improved Procedure for the Imine Condensation Reaction in Undergraduate Laboratories

The imine condensation reaction is commonly addressed in second semester organic chemistry classrooms. With recent pushes toward green chemistry and developing safer reactions, there is a growing interest in attempting organic reactions in the presence of water or aqueous solvents. The work discussed here provides an important update to a previously reported laboratory experiment that utilizes freshly squeezed fruit juices and water as the reaction solvents to compare the reactivity of the imine condensation with respect to steric, electronic, and pH effects. Five different aromatic benzaldehyde derivatives are reacted with n-butylamine, sec-butylamine, and tert-butylamine in the presence of an aqueous solvent. Students from multiple sections were able to successfully perform the updated reaction and analyze the products with 1H NMR spectroscopy, calculate the percent conversion for each reaction, and analyze reaction trends. The conversion rates for this imine condensation laboratory experiment greatly exceed those from our previously reported study which utilized organic solvents ( J. Chem. Educ. 2023, 100 (11), 4456). Strategies for implementation of this updated imine condensation project are presented.

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来源期刊
Journal of Chemical Education
Journal of Chemical Education 化学-化学综合
CiteScore
5.60
自引率
50.00%
发文量
465
审稿时长
6.5 months
期刊介绍: The Journal of Chemical Education is the official journal of the Division of Chemical Education of the American Chemical Society, co-published with the American Chemical Society Publications Division. Launched in 1924, the Journal of Chemical Education is the world’s premier chemical education journal. The Journal publishes peer-reviewed articles and related information as a resource to those in the field of chemical education and to those institutions that serve them. JCE typically addresses chemical content, activities, laboratory experiments, instructional methods, and pedagogies. The Journal serves as a means of communication among people across the world who are interested in the teaching and learning of chemistry. This includes instructors of chemistry from middle school through graduate school, professional staff who support these teaching activities, as well as some scientists in commerce, industry, and government.
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