I have never enjoyed teaching nomenclature, but it is certainly important for students to know what is meant when they see a name out there in the wild. I use Gary's excellent in-class activity (linked below) and then follow up with these slides to cement the knowledge in the last 10-20 minutes of class. The first content slide is a list of nomenclature rules from IUPAC but I normally fill in a list of class-generated rules on the title slide before moving to the truth... our in-class rules are often quite close to the published rules.
Students will cement their knowledge of nomenclature by practicing what they have learned in an in-class activity.
I use this as a call-and-response after students have carried out the in-class activity by Gary Gulliet.
I usually ask 2-4 nomenclature questions on the midterm and on the final. I don't ask for complete adherence to IUPAC rules, but a complete, and unambiguous name is required, including stereochemical descriptors where applicable.
In general, my students do fairly well, but this is a challenge for a small subset of students.