This article describes a comparative assignment developed for a third-year undergraduate organic synthesis course involving a combined laboratory experiment and class exercise. In this assignment, students compare the sustainability of two industrial amination reactions to form the same target molecule (4-(n-hexylamino)benzonitrile): a nucleophilic aromatic substitution procedure (S_NAr) provided in the class exercise, and a Buchwald–Hartwig (B–H) amination procedure completed in the laboratory. The assignment is structured using a “case-study” format to provide appropriate context. Students use industrial solvent and reagent substitution guides, complete process mass intensity calculations, and apply the Twelve Principles of Green Chemistry to compare and contrast the S_NAr and B–H reactions. They finally recommend a preferred reaction procedure after considering multiple sustainability concepts in their analyses. The assignment is highly adaptable as different industry guides may be used and the S_NAr reaction procedure is easily modified. Ultimately, students learn to apply sustainable chemistry principles to industrially relevant reactions, an important skill for their future careers.

中文翻译：

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比较班级和实验室绿色化学作业中的工业胺化反应

本文介绍了为三年级本科有机合成课程开发的一项比较作业，其中涉及实验室实验和课堂练习相结合。在这个作业，学生比较两个工业胺化反应的可持续性，以形成相同靶分子（4-（N-己基氨基）苯甲腈）：亲核芳族取代步骤（S _Ñ在类锻炼提供Ar）和一个Buchwald- Hartwig（B–H）胺化过程在实验室中完成。使用“案例研究”格式来构造任务，以提供适当的上下文。学生使用工业溶剂和试剂替代指南，完成过程质量强度计算，并应用绿色化学十二个原理比较和对比S _NAr和B–H反应。在分析中考虑了多个可持续性概念后，他们最终建议了首选的反应程序。由于可以使用不同的行业指南，并且可以轻松修改S _N Ar反应程序，因此该任务具有很高的适应性。最终，学生学习将可持续化学原理应用于与工业相关的反应，这是他们未来职业的一项重要技能。