Tag: Curved Arrow Notation

It’s My Favorite Time of the Year! Chapters 6 and 7

It’s my favorite time of the year. Finally, we get to do chemistry in organic chemistry! Not to malign BDE, IMF, chair vs. boat conformations, etc., but I have always thought of the stuff leading up to this point—strains and conformers, the designation of stereochemistry and the terms and rules associated with their nomenclature—a bit

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Teaching Solvent Effects Early Helps Keep Students’ Heads From Spinning

We started Chapter 9 in class a couple weeks ago, where we learn how to predict the outcome of the SN1/SN2/E1/E2 competition. Similar to how it’s done in most books, we do this by first learning about the major factors that influence the rate of each reaction in this competition. But unlike other books, this

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When Should Resonance be Taught?

In my textbook, resonance is presented rather extensively in Chapter 1 (“Atomic and Molecular Structure”), ultimately teaching students how to draw all resonance structures of a given species. I like to teach resonance to that depth early in the course because it reinforces topics that are vital to student success throughout the entire year of

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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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MCAT-2015 is Here

The new year traditionally brings a time for both reflection and looking forward. For teachers of organic chemistry everywhere, this past year stands out more than most. After years of planning, MCAT-2015 is finally upon us. I previously wrote about the challenges and opportunities this change holds for us and how we, at Middlebury College,

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Delay Reactions, Hasten Understanding

In my early years of teaching, I would break the ice the first day of class by asking my students what they know about organic chemistry. Without fail, the first student to respond would say something to the effect of: “It’s really hard! I’ve heard that there are so many reactions to memorize!” A low

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Getting Students to Connect Acid-Base Chemistry to the Rest of Organic Chemistry

Many professors agree that a strong foundation of acid-base chemistry is vital for students to understand the great majority of organic reactions they will face, and I firmly agree. Certainly, the importance of acid-base chemistry is reflected by the fact that organic textbooks typically discuss acids, bases, and proton transfer reactions early. Despite these early

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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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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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Is Organizing by Mechanism Necessarily “Higher Level”?

Because organizing by mechanism really helped me turn around my own organic chemistry course, I was eager to share what I had learned. Many instructors I’ve talked to over the years have been very receptive; some have even adopted this organization themselves. But I’ve encountered a good amount of apprehension as well. Some instructors worry

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