The Mechanism Did It!

I finally finished the book last night. In the two years since we adopted Karty, I have taught the first-semester course three times. However, due to the oddities of academic scheduling, this spring was my first time teaching our second-semester course with the text. So, metaphorically speaking, I finally got my chance to find out how the book ends; I got to see how the text works for second-semester curriculum.

Unlike an Agatha Christie mystery novel, the ending—though enjoyable—was not filled with intrigue and suspense. Of course, any instructor who comes within twenty meters of Karty’s text knows immediately that the reaction mechanism is the central, and perhaps only, protagonist. I recently had a very illuminating conversation with a small group of students who described their own discovery of this literary analogy.

These students had taken the first-semester course with me a year ago, but elected to take biochemistry before returning to organic. This trajectory is, in fact, not at all discouraged by our new curriculum. I was eager to hear their views about getting back into the organic chemistry mindset after an eight-month break. I got comments like:  “It came back pretty quickly” and “Going over the new mechanisms helped you to remember everything you learned before” and “Everything still made sense with how reactions worked…I didn’t have to review really.” These comments would have been nice to hear from any students, but were even better from students who had taken such a long break from organic. I was pleased but not surprised. With less to memorize, there is less to forget.

For our last class today, we went through E. J. Corey’s 1969 total synthesis of Prostaglandin F2a. It was like a Greatest Hits compilation for organic synthesis. Substitution, oxidation, reduction, Diels-Alder, Wittig, carbonyl addition, hydrolysis, protecting groups, and more. Students smiled as they met familiar old friends and more recent ones. A few even cheered for the Wittig—a class favorite. It all made sense to them because they had carefully followed Karty’s main character though each chapter.

Yes, the mechanism did it alright. A great ending to the story. Sure, there is more than one mechanism in organic chemistry. Many in fact. From the student’s point of view though, once you know mechanisms, you know organic chemistry. The rest just seems natural.

-Rick Bunt, Middlebury College

Click here to learn more about Prof. Bunt.

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