Tag: Nucleophilic Addition-Elimination

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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Memorization Not a Choice: Mechanisms Matter

I have always approached my organic sequence as a mechanism-driven course. Every reaction that we discussed in class started with a mechanism to show how it wasn’t really anything new, but an extension of the types of behaviors we had learned to describe and anticipate. I avoided texts that listed reaction after reaction as completely

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Proton Transfer: Well Begun is Half Done

Of all the chapters in Joel’s mechanistically organized textbook, my favorite is Chapter 6: The Proton Transfer Reaction. Acid-base chemistry might seem like an odd topic to pick in an organic chemistry textbook. It seems almost…inorganic, a throwback to general chemistry of sorts. So why do I like it so much? It accomplishes two vitally important

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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.