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Introducing Tetrazine Synthesis and Reactivity in Undergraduate Laboratory Internship
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DOI：10.1021/acs.jchemed.6c00133.png)
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Abstract
En 中文
Recent advances in click chemistry have opened promising opportunities for instructional laboratory design, yet heterocyclic compounds such as s-tetrazines─despite their visual distinctiveness and synthetic relevance─remain underutilized in undergraduate education. To meet the instructional need, a short-term undergraduate laboratory internship was designed to introduce first- through third-year students to the synthesis and reactivity of a tetrazine in a collaborative environment. Students learn to synthesize and purify the tetrazine through a straightforward one-pot procedure, followed by performing cycloaddition under ambient conditions. The visually striking transformation, characterized by the disappearance of the red to dark red color, is confirmed by UV–visible absorbance analysis. The experimental protocol is compatible with standard undergraduate laboratory facilities, employing catalyst-free conditions and readily available, inexpensive reagents. The experiment provides students with a structured sequence of reaction setup, purification, and spectroscopic analysis, each reinforcing practical competencies in reaction planning, separation techniques, and instrumental interpretation.
Keywords:
Addition reactions
Chemical synthesis
Cyclization
Students
Undergraduates
First-Year Undergraduate/General
Second-Year Undergraduate
Organic Chemistry
Hands-On Learning/Manipulatives
Laboratory Instruction
Synthesis
Heterocycles
Oxidation/Reduction
Chromatography
UV/Vis Spectroscopy
Qualitative Analysis
Dyes/Pigments
Journal
IF:
2.9
Papers:
1.2K
Citations:
2.3W
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