Abstract: The synthesis of cyclohexene is a classic experiment in basic organic chemistry laboratory courses. Utilizing cyclohexene as a substrate, we demonstrate the significant role of radical reactions in modern chemistry by performing electrochemical C―H bond functionalization. In this study, we achieve the oxidation of the C―H bond in cyclohexene under electrochemical conditions using N-hydroxyphthalimide as both a hydrogen atom transfer catalyst and an oxidizing agent, eliminating the need for additional oxidants. The process employs inexpensive and readily available electrode materials, and the solvent used can be recycled. Furthermore, students can gain fundamental insights into this C―H bond oxidation reaction through electrochemical analyses and bond dissociation energy assessments. The reaction conditions are mild and safe, with a duration suitable for undergraduate laboratory courses. The reproducibility of this method has been validated by multiple undergraduate students.

Key words: Cyclohexene, Electrochemistry, C―H bond, Radical