ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Alejandro Lopez-Ruiz, Mariano Ortega-Muñoz, Francisco Santoyo-Gonzalez, and Alicia Megia-Fernandez

Departamento de Química Orgánica, Facultad de Ciencias, Unidad de Excelencia de Química Aplicada a Biomedicina y Medioambiente (UEQ), Granada, Spain

E-mail: amegia@ugr.es

Received: 27 January 2023  Accepted: 3 May 2023

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.

Keywords: Click chemistry; Cycloaddition; One-pot; Laboratory practice

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02858-5

Chemical Papers 77 (9) 5227–5236 (2023)