An advanced undergraduate organic chemistry laboratory experiment involving a rhodium-catalyzed intermolecular hydrocarbon C–H oxidation reaction is described. In the initial phase of this lab, students conduct a C–H amination reaction of ethylbenzene and isolate a benzylic amine product. In the second part of the lab, competition experiments are performed to compare the relative rates of C–H insertion with electronically disparate para-substituted ethylbenzene derivatives. Reaction progress is monitored by thin-layer chromatography and the outcome quantitatively assessed using ¹H NMR spectroscopy. Data from competition experiments form the basis for a discussion of reaction mechanism including analysis of putative transition structures and relative potential energy barriers for C–H oxidation. Experiments have been designed such that instructors can tailor the level of detail and discussion from introductory to advanced.

中文翻译：

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铑催化的CH胺化反应：CH官能化反应选择性的案例研究

描述了涉及铑催化的分子间烃CH氧化反应的高级有机化学实验室实验。在本实验的初始阶段，学生将进行乙苯的CH氨化反应，并分离出苄基胺产物。在实验室的第二部分中，进行竞争实验以比较C–H插入与电子上完全不同的对位取代的乙苯衍生物的相对比率。通过薄层色谱监测反应进程，并使用¹定量评估结果1 H NMR光谱。来自竞争实验的数据构成了讨论反应机理的基础，包括分析假定的过渡结构和C–H氧化的相对势能垒。设计了实验，以使讲师可以根据从入门到高级的程度来调整详细程度和讨论的水平。