Tag: Nucleophilic Substitution

Seeing the Big Picture

As the semester comes to a close, I have been reflecting on my lectures and experiences with a mechanistically organized course. The Karty text has presented many different types of reactions; from all of the reactions, I want the students to be aware of the central theme in ALL organic mechanisms. In every step, there

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Favorite First-Semester Chapter: Chapter 9

My favorite chapter to teach in first-semester organic chemistry has to be Chapter 9 (“Nucleophilic Substitution and Elimination Reactions 1”) from Karty’s text. The introductions of S­N2/E2 and SN1/E1 reactions begin in Chapters 7 and 8, respectively, but Chapter 9 puts these reactions to the test and suggests to the students that reactions do not

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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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My Most Productive Start of the Semester Ever

The first time I taught out of Joel’s text, I had no idea where I was going to put the semester break. I enjoyed how well each chapter flowed into the next, but that left me wondering where to put a five-week break. I was used to a traditional ordering of subject which resulted in

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No Longer Dreading the Second Exam

Shortly after I began teaching, when I was still using a book organized by functional group, I came to dread the second exam of the first semester. The class would typically perform decently well on the first exam, but scores would plummet on the second one. I recently looked back at my records for a

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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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The Benefits of a Mechanistically Organized Book When Teaching a 2-cycle Approach

Two-cycle organic chemistry is a pedagogical approach that has gained in popularity over the last couple decades. It’s a rather simple idea: The first semester course is treated as something of a survey, dealing primarily with the fundamentals, whereas the second semester revisits many of the same topics from the first semester, but treating them

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Predicting the Products of an SN1/SN2/E1/E2 Competition

When I teach nucleophilic substitution and elimination reactions, I find that students typically have very little trouble drawing each mechanism and predicting the products, so long as they are specifically told which reaction. But many students find one aspect very challenging: predicting the winner of an SN1/SN2/E1/E2 competition. In my first few years of teaching,

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What Reaction(s) Should Come First?