A Racemization Revelation

In my experience, when students are writing a reaction mechanism, the most common error is to form a strong base under acidic conditions or vice versa.  I stress the importance of paying attention to reaction conditions in lecture, but the “function group” based textbook previously used at Western Washington University did not contain a section … Continue reading A Racemization Revelation

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 … Continue reading How the Ten Elementary Steps Unified My Course

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

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 … Continue reading Proton Transfer: Well Begun is Half Done

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, … Continue reading MCAT-2015 is Here

Surprises from Chapter 10

Organizing a course like organic chemistry with dense material and volumes of content to cover can be incredibly daunting. At times, it seems impossible to find a balance between giving fundamental concepts the attention they require and building up the toolbox of reactions for students to use at a reasonable pace. Like many professors, I … Continue reading Surprises from Chapter 10

Chapter 7: Elementary Steps but Giant Conceptual Leaps

If writing mechanisms is like giving good directions, then each elementary step is similar to saying “turn left at the stop sign.”  You might have to turn right many times during one trip just as you might need multiple acid-base steps during one mechanistic pathway. Joel’s “Most Common Elementary Steps” chapter lays out each possible … Continue reading Chapter 7: Elementary Steps but Giant Conceptual Leaps