Skill in organic chemistry nomenclature is fundamental for communicating more complex concepts. Interpreting and using functional group names is particularly important. With nomenclature101.com, students can create tailored interactive quizzes according to their learning needs; the tool is free and available in English and French. The present study investigated students' nomenclature learning in three different learning environments to determine (1) what learning gains participants make when using nomenclature101.com independently, when guided, or taught nomenclature through a traditional classroom tutorial and (2) students' perceptions of the usefulness, ease of use, and overall learning experience in each of the settings. We invited students from first and second semester organic chemistry courses at a large, research-intensive Canadian university to participate in a nomenclature workshop. When participants arrived, they were randomly sorted into one of three treatment groups: classroom tutorial, independent use of nomenclature101, or guided use of nomenclature101. Before the session, participants completed a pre-test; at the end, they completed a post-test and a questionnaire related to affective aspects of their experience. We analyzed participants' scores and questionnaire responses, and qualitatively analyzed their test answers, including errors. Learning gains were significant with large effect sizes for all three groups although there were no significant differences in learning gains between groups. The largest gains were observed in the ability to correctly identify and draw functional groups. Exploratory factor analysis showed that the post-workshop questionnaire about nomenclature101.com reliably measured participants’ perceptions about two latent factors: usefulness and ease of use. Based on questionnaire results, most participants liked the learning tool and found it useful and easy to use. Participants in all groups reported enjoying their learning experience. Few participants postdicted their quiz grades accurately, suggesting that metacognitive skillfulness was lacking among workshop participants. The large learning gains observed after using nomenclature101.com or learning in a classroom setting for just one hour shows the potential that instruction has to help students learn functional group identification skills, which ideally will mitigate barriers to communication and understanding. These results offer flexibility to educators as they make instructional choices such as teaching nomenclature in a course period or tutorial setting or asking students to learn nomenclature independently with nomenclature101.com. Students have the flexibility to work outside of class in the manner of their choosing.