Learning organic chemistry is not a linear process; rather, it’s made up of many small cycles. Each cycle begins when we present students the basic ideas behind a new topic. Then we’ll show students how to apply those ideas toward solving a few initial problems, and we’ll follow that up with an assignment where students solve related problems on their own. Those assigned problems are not only for practice but also are tools to help students identify trouble spots, so they know what questions to ask for help.

And to close the loop, students must get those questions answered in order to address misconceptions and further develop skills before moving on to the next topic. All parts of those small cycles are important, but I might argue that the most vital part is when students generate questions. When students can ask questions that are tailored to themselves, that’s when their learning becomes personalized, and that’s when their learning is most effective and meaningful.

But how can students generate questions to ask? How can students generate the right questions? For me, the problems I assign are front-and-center. I need my students to work on a variety of problems with varying levels of challenge and depth. And I need my students to receive feedback, telling them not only whether their answer is correct or incorrect, but also where they might have gone wrong and why. With that information in hand, a student then has a really good question to ask: “Dr. Karty, I got this problem wrong. This is what I did. Why is my answer wrong?”

When I started my teaching career in 2001, the only problems I assigned came in the form of written problem sets. Those were certainly helpful tools for students to assess their strengths and weaknesses. But there were two major drawbacks, both related to the grading. To give students the proper variety of problems to work on, each problem set ended up being fairly lengthy, so the turnaround time for grading and feedback was also lengthy, about a week. Yes, students received good feedback…eventually. But how effective could that feedback be when it had been several days since those problems were last at the forefront of students’ minds? The second drawback was that, in order to keep students engaged working on problems throughout the semester, I needed to assign one written problem set each week. As you can imagine, probably half my time in a given semester was spent grading written problem sets; the grading felt never-ending.

There needed to be a better way, because as my career was developing, demands on my time were increasing elsewhere: scholarship, leadership positions at my institution, family. How could I regain some time from all of that grading, without compromising student engagement working on problems, without compromising the variety and depth of problems for my students to work on, and without compromising the feedback my students get? And on top of that, how could my students get feedback more immediately? Online homework certainly seemed promising. And a few years into my teaching career, I was already using online homework for my general chemistry course. But in my view, general chemistry lent itself much better to online homework: the problems tended to be quantitative, and as such, it was more straightforward for online homework systems to grade and provide feedback for common wrong answers.

But I had much higher expectations of an online homework system for organic chemistry. For me to get behind one, it had to allow students to draw mechanisms with curved arrow notation, and it had to give feedback when students made mistakes drawing those mechanisms. In the early 2000s, such an online homework system simply didn’t exist. So, my only choice was to stick exclusively with written problem sets.

Figure1: An Animation of the Smartwork mechanism drawing tool demonstrating the ability for students to draw their own curved arrows

Over the next several years, online homework systems emerged for organic chemistry, and sales reps from publishing companies would visit me in my office to promote their system. I would immediately ask: “What do your mechanism problems look like?” And for years, I remained far from satisfied. Sometimes the answer was that there weren’t any mechanism problems at all. Other times the sales rep would show me a problem in which the mechanistic steps were already complete (structures constructed and curved arrows already drawn in), but out of order, and students just needed to click-and-drag to put the steps in the correct order. That just simply wouldn’t cut it; adopting an online homework system at that time for organic chemistry would clearly compromise my students’ learning, compared to what I already had in place for written problem sets.

Figure2: The feedback a student would receive for the previous example as well as the link to the relevant pages of the eBook and the opportunity to try again

Things continued that way until I saw Smartwork in 2014. This time, when I asked to see mechanism problems, I was shown problems where students had to use a drawing tool to actually construct molecules from scratch, and they had to add their own curved arrows. The system graded students on each step of the mechanism and gave feedback for each step that had mistakes. I was sold! I immediately adopted, and I’ve been using Smartwork for my organic courses ever since.

Smartwork has certainly lived up to my expectations, saving me a great deal of time without compromising student learning. In fact, Smartwork has actually enhanced how my students learn, especially as a result of the instant and problem-specific feedback they get. That’s made it so much easier for my students to generate questions to ask, and now I’m finding my students coming to office hours more frequently with good, effective questions in hand. That helps make office hours extremely productive.

Though Smartwork assignments are an integral part of learning for my organic students, I still assign written problems sets. The difference now is that my written problem sets are much shorter than they were before Smartwork (so the turnaround time is also much shorter), and I assign fewer of them—one every 2-3 weeks. One reason I still assign written problem sets is to give my students practice with, and feedback on, actual pencil-to-paper work, because that’s the kind of work they will need to show on my exams. The second reason I still assign written problem sets is to challenge my students with problems that are a bit more in-depth or more elaborate than the ones in Smartwork. And what I’m finding is that Smartwork does a great job bringing students to the level of readiness needed to tackle those problems that are more challenging. In that sense, I use Smartwork more as a formative tool than a summative assessment.

Ultimately, the blend of Smartwork assignments and written problem sets in my organic chemistry courses really helps students succeed in the course. Smartwork and written problem sets are the perfect marriage.

-Joel Karty, Elon University

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