Tag: Enolate

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,

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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

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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

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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

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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

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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

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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

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Reasoning By Analogy

For twelve years I’ve taught organic chemistry to a mixture of chemistry and biology students. I always begin Organic I by asking my students this same question: Why are you taking this class? Some students respond that the curriculum plan for their major or career requires the organic chemistry course sequence. For other students, organic

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Using Resonance Structures to Make Connections Between Mechanisms

Mechanisms can greatly simplify organic chemistry thereby allowing us to draw connections between reactions that might otherwise appear to be unrelated. With some reactions, however, I have found that the way in which the mechanism is presented can have a dramatic effect on whether a student successfully makes these connections. Consider, for example, the halogenation

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Liberation in the Laboratory

One of the unexpected benefits of Joel’s organization was the discovery that students, once they learn the elementary steps common in organic reactions, can perform a limitless—at least in theory—range of experiments in the lab. (In the upcoming textbook, elementary steps are discussed in Chapter 7, midway through the first semester.) Since students have examined

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