Abstract: The rapid advancement of organometallic chemistry necessitates timely updates to undergraduate curricula. This study proposes an extended teaching module designed for advanced undergraduates or students who have completed fundamental organic chemistry courses. Using the mercury-catalyzed alkyne hydration—a textbook classic frequently presented with oversimplified mechanisms—as a foundation, the module thoroughly examines its catalytic cycle to introduce the frontier concept of “transition metal π-acid catalysis”. The curriculum then focuses on environmentally benign and highly efficient homogeneous gold catalysis as a paradigmatic case, systematically elucidating the universal π-coordination activation pattern for unsaturated bonds, critical reactive intermediates, and their applications in cyclization and tandem reactions. The scheme emphasizes seamless integration with prerequisite knowledge, specifies essential learning foundations, and incorporates progressive classroom interactions. Its objectives are threefold: to facilitate students’ comprehensive understanding bridging classical knowledge and cutting-edge research, to develop mechanistic-based analytical skills for solving chemical problems, and to provide educators with a ready-to-implement, structurally complete teaching model.

Key words: Organometallic chemistry, Undergraduate teaching, Teaching expansion, π-Acid catalysis, Gold catalysis, Reaction mechanism