Here at Teach the Mechanism we are excited to introduce you to Dr. Christine Pruis, our full-time on-staff Chemistry Subject Matter Expert. In the following post, Dr. Pruis discusses her journey with authoring the Smartwork5 online homework and how this resource facilitates learning and understanding organic chemistry and mechanisms when paired with Joel’s text. Read more about Dr. Christine Pruis by clicking on the link at the end of this article, or by exploring our “The Bloggers” tab at the top of the blog page. Now, here’s Dr. Pruis:

I first became familiar with Joel Karty’s mechanistic organization in 2011 while working as an Organic Chemistry Senior Lecturer and Lab Coordinator at Arizona State University. I was intrigued by this idea, since its methodology and rationale seemed to resonate with my experience. Then, what I saw in his preliminary manuscript definitively convinced me of the benefits of this organization—this was clearly a worthwhile change. With nearly 600 students in my lecture classes, however, a great book was not enough to force a switch—I also required a robust online homework system to support the mechanism-based pedagogy. As chance would have it, four organic chemistry instructors were being hired to write online homework mechanism questions for the very sort of online homework system I desired. I readily joined the Norton team!

As an instructor for large-enrollment organic lectures I believe formative online homework is pivotal for student learning. It is impossible for any instructor, but especially one teaching hundreds of students, to always identify a mistake right at the moment it is made. Unfortunately, if not corrected promptly, some misconceptions can propagate and continue for the rest of the course. For example, I often saw “backwards” curved arrows in proton-transfer mechanisms at the end of the course despite correcting these erroneous “proton-pushing” arrows on prior tests and worksheets. I strongly believe that for certain types of errors students need to be redirected immediately to ensure that improper notions do not become embedded. Electronic homework can do something which is nearly impossible for an instructor—immediately recognize an error and correct the flawed thought process at that moment. Just imagine a world with no more backwards arrows!

The immediate formative feedback available within the SmartWork5 online homework system is its main advantage over paper-based assessments. The key to this helpful formative feedback is that it is programmed and authored by experienced organic chemistry instructors, such as myself. As an author, I programmed into SmartWork5 common errors I saw students make on written assessments: backwards curved arrows, missing curved arrows, curved arrows ending at the wrong location, curved arrows starting at electron deficient atoms, etc. For each of these scenarios a student is not only marked wrong, but is given specific feedback to help them identify and correct the error. This can be done for each step of a mechanism, often resulting in dozens of programmed responses to a variety of incorrect answers.

Shown in the accompanying image is a seemingly straightforward one step proton transfer between hydroxide and hydrochloric acid. Despite its apparent simplicity, this question has five programmed responses for common errors. The goal is to identify and correct misconceptions early to prevent propagation throughout the course.

Correct answer with feedback:

Personalized feedback based on common incorrect responses:





-Dr. Christine Pruis, W. W. Norton, Chemistry Subject Matter Expert
Click here to learn more about Dr. Pruis

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