As a teacher, I try to remember what organic chemistry was like for me as a student. I know that to be effective instructors, we need to be able to see topics through our students’ eyes. After five years in academia, my list of main organic chemistry takeaways has grown to the following five points:

  • General chemistry is going to come back and be sprinkled throughout the mechanistic perspective of organic chemistry. (Karty does a great job of this!)
  • pKas are essential, so learning functional groups is vital. 
  • Always view each reactionary step as the nucleophile moving toward the electrophile.
  • The professor is on the students’ side and is not intentionally making this course harder. 
  • Practice, practice, practice!

First, general chemistry is the underlying theme to the mechanistic style of organic chemistry. I was taught by a non-Karty text, but I am now a believer in Karty’s book. In his text, concepts are presented in an order that requires students to remember older material. In the list below, I wrote the organic topic first and then the supporting trend from the “gen chem” days in order to highlight the important relationship between organic and general chemistry. 

  1. MO Theory; Hybridized Orbitals vs Atomic Orbitals
  2. Number of Hybridized Orbitals vs Atomic Orbitals; Conservation of Energy
  3. Energy Diagrams; Pauli Exclusion Principle, Aufbau Principle, and Hund’s Rule
  4. Strength of Nucleophilic Species; Periodic Table Trends

Second, I note that pKas are very helpful when learning various topics, ranging from ranking acids and bases to equilibrium constants, especially in a tough chapter like Chapter 6, which deals with proton transfer reactions. Honestly, I don’t know how I got through my undergrad chemistry courses without knowing pKa values. But my goal is to have my students learn from my past mistakes, so I explain to them that pKas are essential to know, even though there are so many to keep track of! I suggest that learning pKa values by functional group is the best way for my students to equip themselves with the right tools to understand the material. Because pKas are influenced by electronegativity, carbon content, and atomic radius, we see that, again, the trends from gen chem come in handy for organic topics! 

Third, I try to make reactions seem less scary by viewing each reactionary step as one in which the nucleophile moves toward the electrophile. Students can get lost in all the names of reactions. However, if they look at each mechanism, it boils down to identifying arrow movement and whether the negative species is moving to the positive species. I try to stress these key points to my class and express that if they ever get stuck on a problem, they should always look to see how they can move the electrons and flow the species from negative to positive. 

Fourth, I try to remind my students that I, as their professor, am on their side and that I am not intentionally making this course harder for them. I know how challenging this content can be, so I offer countless amounts of practice, weekly office hours, and time to routinely answer questions. In general, I provide rules of thumb (ROTs) to help my students maneuver through tricky topics. I also offer review sessions prior to every test. To do so, I have arranged my course so that the class session prior to each midterm and final is set aside to review for the upcoming exam. Because reviewing material is so important in organic chemistry, I emphasize how important it is that students practice, practice, and practice! This ties into my recent post in which I encourage students to engage in pen-and-paper exercises (solving problems by hand) so that course material is pushed from their short-term to long-term memory.

Whenever I refer back to my list of takeaways, I realize that these points will need to grow and expand so that they meet the needs of my students throughout all my years of teaching. That’s why I frequently try to imagine what my own students are going through, especially now with online classes. For me, personally, I know that I would miss that in-person, “organic” style of learning because online classes truly force students to be more diligent and add another degree of separation between students and professors. I understand how this can make my students’ experience feel even more daunting for a course as challenging as organic chemistry.

But because I love this subject so much, it is an absolute joy for me to teach it by making the material appeal to my students while also maintaining the rigor and integrity of the content. Even though I know that most of my students aren’t as passionate about organic chemistry like I am, I do know that my students love to learn in their own unique ways, so I view my excitement as a catalyst to help my students continue to progress and succeed in their educations and vocations at large.

-Kerri Taylor, Columbus State University

Feel free to share what you’re doing with your online classes this fall in the “Comments” section below!

Click here to learn more about Kerri Taylor!

Click here to read all posts by Kerri Taylor!

One thought on “If I Could Turn Back Time

  1. Kerri, great points.

    Having students know pKa values is definitely valuable when it comes to learning mechanisms! Often I’ll use pKa values to illustrate the difference between a reasonable versus an unreasonable mechanism. For example, if I ask students to predict the outcome when an ether is treated with water, students know that an alkoxide anion is unsuitable as a leaving group. What some students will do, however, is use water to protonate the ether oxygen to make a good leaving group, and then they will proceed with an Sn1 or Sn2 mechanism. In those cases, I’ll use pKa values to show students that the first proton transfer (the one that makes a suitable leaving group) has the REACTANTS favored by about 10^14, so there will effectively be no reaction.

    Also, absolutely, telling students “I’m on your side” is really powerful. Many students already come into the course feeling like they need to battle the material…it’s not easy… Students need to be reassured that they aren’t battling the professor, too! That SHOULD go without saying…it’s obvious to us, but it’s not always obvious to students.

Leave a Reply