This article describes one of the projects in the advanced undergraduate organic chemistry laboratory course concerning the synthesis of two local anesthetic drugs, prilocaine and benzocaine, with a common three-step sequence starting from toluene. Students undertake, in a several-week independent project, the multistep synthesis of a pharmaceutical drug, comprising instructor-guided tasks such as literature search, planning, critical discussion, experimental design, observation, and results interpretation. In this project, in addition to searching and using information found in primary and secondary sources, students learn to design the methodology for several of the steps in the reaction sequence, bearing in mind safety and environmental concerns. (Contains 1 scheme.)