Abstract: To bridge undergraduate laboratory instruction with cutting-edge synthetic methodologies, this experiment is designed within the context of transition-metal-catalyzed activation of inert chemical bonds. It presents a comprehensive organic chemistry experiment in which naphthalene is synthesized from 2- naphthalenemethanol via a palladium(II) acetate-catalyzed oxidation-decarbonylation reaction. This transformation offers advantages such as high step economy, a clear mechanistic pathway, and strong pedagogical adaptability, enabling the integration of advanced synthetic knowledge with fundamental laboratory training within a single experimental framework. By combining traditional organic chemistry experiments with modern synthetic approaches, students not only acquire essential experimental skills but also gain insight into the mechanisms of inert bond activation and reorganization, as well as the design principles underlying advanced organic transformations. Furthermore, the processes of product structure analysis and reaction pathway elucidation encourage students to transition from passive learning to active inquiry, thereby fostering systematic thinking, problem-solving abilities, and scientific awareness. As such, this experiment enriches the content of undergraduate organic chemistry laboratory instruction, reinforces the understanding of green synthesis concepts, and holds pedagogical value in enhancing students’ comprehensive competencies and supporting their initial research training.

Key words: Transition metal catalysis, Decarbonylation, Chemical experimental teaching, Naphthalene, 2-Naphthylmethanol