Click to learn, learn to click: undergraduate synthetic organic chemistry experiments

Abstract

The optimization of an undergraduate experiment for Organic Chemistry students is described to explore the concept of click chemistry. The preparation of a terminal fluorescent alkyne and an organic azide is reported consisting of simple steps. These are employed in the Cu(I)-catalized azide-alkyne cycloaddition to obtain a novel molecule containing a triazole ring whose characterization allows the students to practice a variety of techniques: NMR (1H, 13C, COSY and HSQC), melting point, thin layer chromatography, IR, fluorescence spectroscopy and mass spectrometry to confirm the structure of their obtained product. An alternative methodology in a one-pot reaction is also explored and a full laboratory manual provided.