Tag: Resonance

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

Read More

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

Read More

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

Read More

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

Read More

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

Read More

Teaching the Mechanism Means Testing the Mechanism

Exam questions are a primary medium by which students learn what their instructor values most in the course. If we evaluate what we value, questions should test the mechanism and thus emphasize conceptual understanding, utilize real applications, and require deep thinking. And for me, the most important reason to pose mechanistic questions is to see

Read More

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,

Read More

POGIL and Mechanisms are Natural Allies

Choosing a textbook is always an important part of class preparation, but when using Process Oriented Guided Inquiry Learning (POGIL) with a group of students of mixed academic and reading abilities, the choice is perhaps even more important. POGIL is an evidence-based teaching/learning method used across the country. Students work in structured groups to complete

Read More

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

Read More

Solving the IR Puzzle

My three year old son recently has shown interest in solving puzzles. He dumps the pieces on the floor and randomly clicks them together until he finds a match. This is often the same approach that students take to problem solving in organic chemistry. To help my students work more systematically, I introduce IR early

Read More