Abstract: Conventional organic reaction mechanisms primarily encompass three categories: ionic reactions, concerted reactions, and radical reactions. While current undergraduate organic chemistry laboratory curricula predominantly emphasize the first two types, radical reactions remain notably underrepresented. This pedagogical gap necessitates the inclusion of relevant experimental procedures to facilitate students’ fundamental comprehension of radical reactions and their condition optimization. Given that organosilicon compounds not only serve as crucial synthetic intermediates but also demonstrate diverse biological activities and substantial applications in materials chemistry, this experiment employs 4-chloroquinoline and triisopropylsilane as starting materials to synthesize 4-chloro-2-triisopropylsilylquinoline through an electrochemically mediated radical pathway. Designed for undergraduate chemistry education, this experiment integrates radical chemistry with modern electrochemical synthesis techniques, aiming to broaden students’ perspectives on reaction mechanisms, introduce contemporary synthetic methodologies, foster innovative thinking, and enhance engagement with organic chemistry. The protocol adheres to green chemistry principles, exhibiting superior characteristics including operational efficiency, exceptional atom economy, high product yield, and excellent reproducibility.

Key words: Radical reaction, Electrochemical synthesis, Organosilicon compound, Undergraduate experimental education