Tag: Nucleophilic Addition

All Downhill After the Aldol

Ah yes, it is that time of year again; a seven week coast to the Organic Chemistry II finish line. All the elementary steps have been introduced and discussed multiple times and it feels like review from here. Most texts seem to end with reactions like Aldol condensation and Robinson Annulation. A functional group approach

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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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Six Things Students Should Be Able to Do upon Completing Chapter 7, and One Thing They Shouldn’t

In my previous post, I described how happy I’ve been with my students’ ability to process the relatively complex interplay between kinetics and thermodynamics to understand the outcome of a competing set of chemical reactions. The specific example I gave involved the competition between transesterification and the Claisen condensation reaction, and that got me thinking

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Ending on a Good Note

A few days ago I returned the second exam of organic II, the bulk of which covered nucleophilic addition and nucleophilic addition-elimination reactions. The following day, a student came to my office to ask questions about the problems she missed. This particular student got off to a rocky start at the beginning of the semester

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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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Improvements on Retrosynthetic Analysis

Success in organic chemistry is heavily reliant on a student’s ability to identify patterns. Until recently, I organized my course by functional group. It was only after I adopted Joel Karty’s approach that I recognized that the variety of reactions used to synthesize each functional group can vary widely and that this variance makes it

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Taking Students Beyond the Limitations of a Functional Group Organization

I’ve written earlier about the advantages of the chapter on elementary steps and how students’ benefits from a mechanistic organization surfaced in the second semester course. In this post, I’d like to offer an example of how this approach allows students to solve problems that I once considered too “advanced” for typical organic students.