Cutting off the Tail

It’s been two years since I started teaching from Joel’s text and I’ve written several times about what motivated us to adopt it in the first place. As scheduling luck would have it, I have taught our first semester course three terms in a row now. Things have really hit their stride in a number of ways. I am still quite happy with the mechanistic focus of the book. Less memorizing; more understanding. No buyer’s remorse here. I am also much more comfortable and fluent with content and organization. I can better anticipate when and where students will have questions. I even think, perhaps somewhat immodestly, that I am a better teacher with this text.

One of the biggest concerns we had at Middlebury going into our new curriculum in tandem with Joel’s new text, was about the level of course difficulty. We were ambitiously incorporating most of carbonyl chemistry into the first semester. We jumped right from substitution and elimination reactions (Chapters 7-9), right to, what is for many, the heart of the second semester material (Chapters 17, 18, 20, and 21). Wow! Out of the frying pan and into the fire, so to speak. How would the students respond though?

The answer is quite well, actually. When we are in the thick of carbonyl additions, I will sometimes remind students how hard they thought stereochemistry and SN1, SN2, E1 and E2 mechanisms were when we first learned about them. One or more students will invariably comment that they wished it was THAT easy now. I just quietly smile to myself with the satisfaction of a job well done. Carbonyl additions will be complicated for a while, but they will be THAT easy eventually. The mechanistic reinforcement just makes sense to them. Organic chemistry will never be an easy course, but the mechanisms make it manageable.

So what have I noticed most after three semesters of Orgo I? I look at exam and course grades as histograms to help me gauge the class performance and to let students gauge their own performance. And the histograms look different than they used to. Getting an A is, perhaps, a tad more difficult as the course content is more ambitious and advanced—as a one semester organic course leading into biochemistry has to be. The students love getting to biological applications (e.g., fatty acid biosynthesis) at the end of the first semester. And they are doing great in biochemistry too! But even more important to me, the tail end of the grade distribution in organic chemistry is much thinner and in some cases gone. Fewer students are earning a D or an F (almost none, in fact). Even the C’s are fewer and farther between. Student performance has improved; I must be a better teacher. Shhh, don’t tell Joel!

-Rick Bunt, Middlebury College

Click here to learn more about Prof. Bunt.


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