Craig D. Campbell, Thomas C. Birkett, Malcolm I. Stewart
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引用次数: 0
Abstract
By adapting a well-established expository style practical on the topic of chemoselectivity, we present our successful approach to introducing elements of guided inquiry and decision-making to novice undergraduate chemists. Using nitroacetophenone as the polyfunctional substrate, students investigate the effect of using two different classes of reducing agents (reducing metal vs hydride donor). By changing the emphasis of the practical to be investigatory in nature, students actively deduce the outcomes of the different reactions, choosing suitable spectroscopic techniques to establish product identification. This enables students to take greater ownership of their learning, leading to the development of higher-level cognitive skills and improved engagement. While the originally reported NaBH4/EtOH reduction proceeds smoothly, significant issues encountered with product isolation using the Sn/HCl reduction conditions meant that a new alternative was required. We report here the use of Fe/NH4Cl as a superior reagent combination, maintaining complete chemoselectivity but providing numerous other benefits. Comparison between the two reducing metal reductions provides a useful scenario for discussion of sustainability in chemistry. Thin layer chromatography (TLC) reaction monitoring, including analysis of TLC-mass spectrometry data, are new facets to the investigative nature of this part of the practical and allowed students to postulate reduction to the hydroxylamine intermediate.
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.