Students learn most effectively when they engage earnestly in solving problems, and receive immediate assessment of their work while their thoughts are still fresh. That is why I moved to a flipped classroom years ago, where I have students prepare for each class by reading about a dozen assigned pages from the textbook. In class, roughly every 10 minutes, I supply the class with a problem to solve, and they take a few minutes to work on the problem and submit their answer through their clickers (knowing that their performance on these clicker questions will count as a small portion of their course grade). After I reveal the correct answer, we then take a few more minutes to discuss the problem and related concepts as a class. Then it’s on to the next clicker question. This clicker-question format for class works particularly well when I want to assess students’ understanding of specific concepts, but it doesn’t work as well for helping students learn to draw mechanisms. That’s because my clicker questions are limited to either multiple choice or short answers (text or numerical)—types of questions that don’t lend themselves well to giving students timely feedback on mechanisms they actually draw themselves. That’s where Smartwork comes in. I’ve been an avid user of Smartwork for online homework for years, but only this semester did I decide to incorporate Smartwork in class as part of teaching mechanisms. Spoiler alert: This has been one of the best decisions I’ve made in my entire teaching career!

Before I talk about why it has worked so well, let me first explain how I have my students work through Smartwork mechanism questions in class. I still have assigned reading from the textbook for each class period, so students come having familiarized themselves with the mechanisms of the day. In class, I post just one mechanism problem at a time on Smartwork, and I ask students to work their way through it, beginning on their own before consulting their neighbors. What’s key is that I set up these Smartwork mechanism questions with infinite attempts and no penalty for wrong answers, and I tell students to submit each time they have completed the next available box. That way, a student doesn’t spend time on the next box until they know the previous box (structures and curved arrow notation) has been done correctly. If they receive a green check mark for a box, they move on to the next box, but when they see a red X appear, they know that something has to be fixed before moving on.

A minute or so after students begin working on the Smartwork mechanism problem, I’ll ask if anyone has a general question, and if so, I’ll address it to the class. Then, I’ll start walking throughout the room, looking in particular for those green check marks and red Xs, which are really easy to see on students’ laptop screens. Invariably, some students already will have accrued a handful of green check marks, and I’ll give those students acknowledgement with a “nice job, keep it up!” If I see a student who still has a red X on the first box, I’ll stop and work with them directly, so they can get the mechanism going. I try to work with a handful of different students as I walk around, and after a few minutes, I’ll call time and take down the Smartwork question (though the question ends up being available for additional practice after class ends), and I’ll ask for students’ attention back at the front of the room. At the white board, I’ll quickly draw the complete mechanism the class was just working on, and I’ll take additional questions before moving on to the next Smartwork question.

Why am I so excited about these Smartwork mechanism problems in class? It begins with active learning. In prior years, when I was using multiple choice clicker questions to assess students’ understanding of mechanisms, it was too easy for students to submit an answer without actually having worked on the problem in earnest. In other words, it was too easy for students to be passive. But with Smartwork, students are actively working on the problem from start to finish. And their motivation for working actively is ramped up when they know I’m walking throughout the classroom checking people’s work.

I’m also really excited about the instant assessment/feedback students receive while drawing mechanisms, especially when it comes to common mistakes. When I find that several students have made the same mistake while working through a particular Smartwork mechanism problem, I’ll take a minute to address it in real time, as a class, so everyone benefits. I’ve done this, for example, when multiple students attempted to deprotonate an aldehyde carbon as the first step of an aldol addition:

I’ve also done it when multiple students tried to construct the mechanism for the LiAlH4 reduction of a nitrile with alternating hydride additions and proton transfers:

Yet another reason I’m so excited about Smartwork mechanism questions in class is that it helped me to quickly learn which students are struggling and need more of my attention. In prior years, I often didn’t have the best sense of who is struggling until a substantial quiz or exam. But this semester was different. Even on the first day of class, when I was walking up and down the aisle, I found that I was stopping to help the same students from one Smartwork mechanism problem to the next. As a result, very early on I was able to start giving more attention to students who needed it the most.

Finally, I’m so glad I decided to incorporate these Smartwork mechanism problems in class because it’s allowed me to make stronger connections with my students. When I routinely walk the aisles to affirm their good work, and stop to help struggling students, it becomes abundantly clear to them that I care. In the days since Covid hit, it is more important than ever that our students know how much we care about them and their success.

Admittedly, my class size is pretty small this semester, as I have just 22 students, but it should be very manageable to incorporate Smartwork mechanism problems in large classes. If you have TAs who attend class, they can help you walk the aisles while students are working, and they can stop to help when they see several red Xs on screen. If you don’t have TAs, you might have students work in small groups from the get-go. That way, students who are more prone to struggling can still make progress. And you could walk the aisles to gain a sense of the trouble spots students are running into, giving you the opportunity to address common mistakes or misconceptions in real time to the entire class.

Again, incorporating Smartwork mechanism questions in class has been one of the best decisions I’ve made in my teaching career. It has made my teaching of mechanisms higher-impact. It has made me a better teacher.

-Joel Karty, Elon University

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