Huifa Han, Yali Qin, Fan Wang, Ning Ding, Fang Fang, Lihong Hu, Hongming Jin* and Yinan Zhang*,
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Two-Step Synthesis of 4-Hydroxy-3,5-dimethylphenyl Benzoate: Undergraduate Organic Laboratory of Electrophilic Aromatic Substitution and Nucleophilic Aromatic Substitution
Electrophilic aromatic substitution (SEAr) and nucleophilic aromatic substitution (SNAr) reactions are among the most valuable reactions in the conversion of aromatic rings. While these reactions are typically covered in separate experiments in undergraduate organic courses, a continuous experimental setup elucidating both SEAr and SNAr processes remains unexplored in the literature for undergraduate laboratories. We herein described a two-step experimental design to cascade the SEAr and SNAr reactions, aiding students in better understanding the similarities and differences of these conversions as well as introducing the concept of umpolung. The experiment also reinforces students’ proficiency in fundamental organic synthesis techniques and workup procedures, such as TLC analysis, chromatography purification, recrystallization, and handling LRMS and NMR.
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.