Finally, An Online Homework System for Organic Chemistry That Is Worth the Investment!

About ten years ago, I attended a presentation that showcased a computer-based homework system for organic chemistry. I liked what I saw, especially in terms of its overall quality and the thought that went into writing the problems. I was intrigued, even excited about it, because I knew how valuable instant feedback is to student learning. Moreover, the demands on my own time were increasing (research, administrative work, my son’s soccer games…), so it was becoming more challenging for me to grade and turn around written problem sets in a timely fashion.

My heart sank, however, when we were shown a typical problem dealing with mechanisms. The problem dealt with a Fischer esterification reaction; it gave students all six of the completed elementary steps, with the curved arrows already included, but the steps were out of order. Students were asked to arrange the steps in order. I remember being disappointed, thinking: “That’s not what I ask my students to do on exams.” For the next several years, every time I was asked to look at an online homework system, my very first question was: “What do the mechanism problems look like?” What I was shown continued to disappoint.

My disappointment ended this past year when I adopted SmartWork for my organic course. The sophistication of the mechanism problems had taken a dramatic leap forward. Its drawing tools allow students to draw molecular structures and add their own curved arrows. And every problem has hints and user-specific feedback, depending on the answer a student submits.

In the early going, I really like the results. Perhaps what is most impressive is the impact on my students’ performance on the first-semester ACS exam. Until a year ago, my students were averaging around the 50^th – 55^th percentile. This past fall, however, my students made a big improvement, averaging in the 65^th percentile—the highest I’ve ever seen! I attribute at least some of this to SmartWork’s ability to give my students a more consistent focus on mechanisms (working closely with these students throughout the semester, I saw nothing to suggest that this cohort is more talented than in previous years). Students could see where they were going wrong in real time, and were therefore able to make important corrections to their reasoning in real time—either on their own or with some help from me.

In addition, SmartWork’s mechanism problems help prevent proliferating bad habits, especially with drawing curved arrows. As an example, SmartWork doesn’t allow students to begin a curved arrow from an atom or a charge. Rather, students must first add a lone pair to the atom, and then must begin the curved arrow from the lone pair.

With the benefits that SmartWork affords my students, I felt comfortable cutting the content on my written problem sets by about a factor of three. I decided not to give up written problem sets entirely, for three reasons. First, as good as SmartWork is, there is still no substitute for grading and feedback by an actual human being. Second, I feel that it is important for students to practice drawing mechanisms by hand, the same way that they will be expected to do on my exams. And third, although SmartWork has a large number of very good problems, it doesn’t have every problem. Therefore, my problem sets are a way to supplement SmartWork assignments with a few deeper and more challenging types of problems.

I’m very happy with SmartWork. It has benefited my students and, as I had hoped at the outset, it has helped me save considerable time, too. I can now spend more time doing other important things, including working with students in office hours, and spending time with my family!

-Joel Karty