Visual analogies play an important role in the teaching and learning of many diverse topics in chemistry. Organic nomenclature is an essential skill needed for student success in organic chemistry; however, it is a topic most students have difficulty in mastering. Without a strong foundation of nomenclature, students will struggle to follow more advanced organic chemistry topics. The project described uses the analogy of a mailman, who is new to an area and trying to remember the destinations of his postal route, to teach alkane nomenclature. Once students master the topic of alkane nomenclature, they are ready to take on the task of naming other organic molecules. Application of the Teaching-With-Analogies (TWA) model defines a stepwise approach to generate an effective analogy and hence was used in the development of the mailman analogy. An easily understandable picture of a mailman, a route system, and housing along the route provides an analogy capable of developing students’ understanding of alkane nomenclature in organic chemistry. The assessment of student learning gains was performed in two different settings (Analogy versus Nonanalogy Groups) and it reveals that students who learn nomenclature with the analogy retain their learning gains through the course, whereas students who learn nomenclature without the analogy lose some of their gains as the semester continues.