Ten Elementary Steps Are Better Than Four

Mechanisms can greatly simplify learning organic chemistry because the hundreds of reactions that students need to know have mechanisms that are constructed from just a handful of distinct elementary steps. This is easy for us professors to see—after all, we’ve been through the year’s reactions and mechanisms multiple times. Students, on the other hand, must … Continue reading Ten Elementary Steps Are Better Than Four

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

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 … Continue reading Seeing the Big Picture

pKa Values: A Chemist’s Best Friend to Predicting a Reaction

Proton transfer reactions are described in Chapter 6 of Karty and are the students’ first experience with a general reaction. When introducing this material to my students last week, they were a little nervous when I said the word “reactions.” I told them that my job, in guiding them along their organic chemistry journey, was … Continue reading pKa Values: A Chemist’s Best Friend to Predicting a Reaction

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

No More Fearing Alkenes and Alkynes

Since this is the second year I am using Joel’s text, I was sure that I would be comfortable with the syllabus and schedule I set. But I again became nervous as I approached Chapter 11, “Electrophilic Addition to Nonpolar Pi Bonds.” Years of slogging through additions to alkenes and alkynes, working example after example … Continue reading No More Fearing Alkenes and Alkynes

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 … Continue reading Teaching Solvent Effects Early Helps Keep Students’ Heads From Spinning

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 … Continue reading Memorization Not a Choice: Mechanisms Matter

Starting the Semester with My Biology Students in Mind

Like so many other organic courses, at my school approximately two-thirds of organic students are biology majors. Of these, most have some sort of pre-health professional aspiration. Because of this audience alongside my chemistry and biochemistry majors, I come to my organic classroom (as I know many of you do!) with two sets of course … Continue reading Starting the Semester with My Biology Students in Mind

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