Right Where I Want my Students to Be

The other day, while working through Chapter 21, I left class with a great feeling as a result of having given the following clicker question: My students were able to rule out choice (a) on their own, given that there’s no reasonable mechanism to arrive at that product with the methyl groups located there. However, … Continue reading Right Where I Want my Students to Be

When to Introduce Conjugate Addition: Sometimes More is More

There were two places in Joel’s text that surprised me: where 1,2 versus 1,4 addition to a conjugated diene appeared—Chapter 11—and where direct versus conjugate nucleophilic addition to polar pi bonds appeared—Chapter 17. Both of these chapters introduce basic concepts and then expand all the way to complex applications, much further than a functional-group organized … Continue reading When to Introduce Conjugate Addition: Sometimes More is More

How the Ten Elementary Steps Unified My Course

For years I told my students they shouldn’t merely memorize a list of reactions. But what were my actions really telling them? In the last textbook I used, the alkene chapter began with nomenclature, then covered Markovnikov addition of H-X and water, halogenation and halohydrin formation, and ended with hydroboration/oxidation. The next chapter that covered … Continue reading How the Ten Elementary Steps Unified My Course

Taking the Enolate off the Pedestal

I’ve noticed over the years that when I put a “name” on something, students tend to panic. We will be doing just fine with SN2 reactions, but when I suddenly name it the Williamson Ether Synthesis, my students become very concerned, as if it’s some completely different concept. Whenever I bring up the Williamson Ether … Continue reading Taking the Enolate off the Pedestal

Do Your Students “Get” Aldol Reactions?

As a new professor, I had mixed feelings about spring break. On the one hand, I was so ready for a vacation, but on the other, I remembered what it was like as a student that time of year. Your mind is on anything but classes. Not only are you looking forward to a week … Continue reading Do Your Students “Get” Aldol Reactions?

The Organization Makes Mechanisms Part of the Routine

A number of years ago I had a student come to me at the end of Organic II and ask, “What happened to the SN2 reaction?” She wanted to know why we had spent so much time on this one reaction in order to move on to the next unit and then never discussed this … Continue reading The Organization Makes Mechanisms Part of the Routine

Demystifying Enolate Chemistry

In my mind, enolate chemistry is one of the highlights of the second-semester organic chemistry course. Granted, the list of named enolate-based reactions (Aldol, Claisen, Michael, Robinson, etc.) can be daunting to students. Nevertheless, the importance of enolate chemistry in biochemical processes (glycolysis, gluconeogenesis, fatty acid biosynthesis), as well as in the synthesis of compounds … Continue reading Demystifying Enolate Chemistry