As a cross-cutting and comprehensive subject, medicinal chemistry involves the knowledge of chemical, biological, medical, and pharmaceutical sciences. A comprehensive medicinal chemistry experience for undergraduates is expected to train various experimental skills and enhance their scientific research ability. Herein, a series of laboratory and computational experiments performed by undergraduate students were described, including synthesis, acetylation, and activity testing of an acetylcholinesterase inhibitor, tacrine. The inhibition activities of tacrine and acetylated tacrine were discussed based on the results of computer simulations. Moreover, representative student-generated data, methods of the experiments, and an interpretation of student feedback on the project are presented.