Golf can frustrate my husband more than any other sport he plays. He recently asked a friend, who is a golf instructor, how to improve his game. The friend responded by saying that, “Practice does not make perfect, practice makes permanent.” If you are practicing with errors, it does not matter how much you practice, those errors become a permanent part of your game. This applies to my organic chemistry students, too, and it wasn’t until I heard this phrase that I thought hard about the type of practice that my students carry out.

I tell my students that working problems is their form of practice in preparation for exams. A runner will log hundreds of hours in preparation for a meet. In the same way, a student will not be ready for an exam unless they log some serious hours working through problems. If a student learns a concept incorrectly and then applies this incorrect thinking to problem solving, the faulty thinking may become permanent.

With over 200 students in a section, it can be challenging for me to catch faulty thinking or address misunderstandings before they become permanent. It was impossible before I started using online homework (I use SmartWork). Online homework allows me to require students to do homework on a regular basis. SmartWork allows me to analyze how the group performs on an assignment or a specific problem, and I can see how each student has answered a problem. Students receive feedback and hints immediately in order to correct their mistakes and to address common misconceptions. On our third exam in Organic I, students had more success in solving multistep mechanisms than ever before.

The first multistep mechanism introduced in a mechanistically organized organic chemistry course is the unimolecular substitution mechanism, SN1. This mechanism involves several elementary steps and students typically have a difficult time understanding how to put all of the steps together. This past fall, I assigned two multistep SN1 mechanism problems in SmartWork. Every SmartWork problem has directed feedback for students. For example, if a student draws a backward arrow in SmartWork, the problem will be marked wrong and the system will provide feedback that helps the student know what is wrong with their answer.


For multistep mechanisms, SmartWork grades each step (answer box = step) individually and provides feedback when only one step has an error. For example, in the problem below, there are four boxes a student needs to complete correctly in order to earn full credit for the problem. In the screenshot I have selected, the student made a mistake in box 3. The student receives feedback for their mistake in box 3, and the feedback appears close to box 3 so that the student knows where the mistake was made.


This is the type of problem I would normally assign for homework, go over in class, and have on a exam. I would ask students to provide the stepwise mechanism for the following reaction:


This semester, more students provided a correct answer than ever before. I received very few backward arrows, SN2 attempts, or incorrect deprotonation steps. Students knew that this reaction mechanism involved three elementary steps (heterolysis, coordination, and proton transfer) and were able to put the elementary steps together correctly. The only variable that changed this term was using SmartWork, and I attribute this success to not only more, but better practice. The hints and targeted feedback that SmartWork provides helped my students make correct thinking permanent. Imagine if golf pros were available 24/7 and were this easy (and inexpensive) to use! My husband might never come home…

— Marie Melzer, Old Dominion University

Marie Melzer teaches a mechanistically organized course at Old Dominion University. She plans to use Joel Karty’s book in the fall (2014)Click here to learn more about Prof. Melzer.

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