As teachers, we are expected to be the experts in our subjects. But the act of learning itself is a constantly evolving process, which is why I find it refreshing when my students ask smart questions and suggest alternative perspectives to keep me on my toes in class.

We have recently transitioned from the electrophilic addition of alkenes to 1,2- vs. 1,4-additions onto dienes. I can’t tell if my students are particularly excited about this topic, but I know that they want to master the concepts. Our lecture started like any other: I presented examples that we worked on together while providing background on the material and organic reactions. I found it quite inspiring to see my students so focused on only our second day of face-to-face instruction (but in our third week of the semester due to our extended-classroom format). 

I was also quite pleased with the following questions my students asked:

  • What temperature is best for kinetic vs. thermodynamic products?
  • How do you know which product (thermodynamic vs. kinetic) is formed?
  • Can we, by default, say that one addition is specific to kinetic vs. thermodynamic products? 

Based on these phenomenal questions, I created the comparative list below to help my students organize the differences between kinetic and thermodynamic products.

Low T (-80-0°C)High T (RT to above)
Low transition state energyHigh transition state energy
More stable carbocationLess stable carbocation
Less substituted double bond ~ less stable productMore substituted double bond ~ more stable product

This list allows students to see the reactions in each particular situation, which teaches them to assess the problem as a singular entity. Even though this resource may not necessarily make this topic less complicated, it will offer students a “cheat sheet,” which usually helps them ask better questions by thinking more like chemists!  

As another example of my students’ developing analytical skills, we were discussing Problem 11.18 from the Karty text, which asked students to find the starting material for the products provided below. 

In class, I presented my own notes and thoughts below on how to best approach this question using the products that were provided. My answer, 2-ethylpenta-1,3-diene, was different from the one in the Solutions Manual. In response, one of my students asked if the addition of HCl could be done by looking at the products from another angle: the left to the right rather than the right to the left. I exclaimed “Great question!” and proceeded to explain the validity of the student’s thought. After completing the problem from left to right, I got the answer of 3-methylhexa-2,4-diene, which is the answer printed in the Solutions Manual. 

Initially, I was not a fan of students finding flaws in my teaching. However, over my six years as an instructor, I have changed my stance on this approach because it offers me a new way of evolving alongside my students. Nowadays, I embrace when my students catch anomalies in the content and ask insightful questions. Sometimes, I even intentionally present them with minor roadblocks (any “known” mistakes) so they can build confidence in their grasp of the material and in themselves. Although the fundamentals of organic chemistry may not change drastically over time, the learning process can and often does, which is why I’ve grown to center my teaching on navigating this delicate balance for the success of my students.

-Kerri Taylor, Columbus State University

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