Digital practice tools support online learning in math, language, computer science, and other subjects, but practice with problems whose answers are not well represented by text or quantities is underrepresented in the digital learning ecosystem beyond multiple-choice questions. This thesis project explored an alternative to multiple choice practice problems in organic chemistry that does not rely on a molecule drawing interface. This project included development and evaluation of a proof-of-concept digital practice tool for chemical resonance problems. Results of a utility study strongly suggest that the practice tool could fill a learning niche within organic chemistry practice as part of a larger integrated learning environment. The study supported the idea that the digital practice tool and others like it can meet different needs for certain learners, such as reinforcing concepts visually, allowing learners to pace themselves, encouraging learners, and providing immediate feedback. Lastly, this project identified generalizable design challenges for similar practice tools, including the need for a known deployment context, curating content for diverse learner backgrounds, and managing appropriate difficulty for diverse learner backgrounds and needs
