If H Is on the Horizontal…Then It’s Horribly Wrong

As an organic chemistry professor, I find that Fischer projections are one of the more challenging perspectives to view chiral centers. However, this projection also happens to be one of my favorites for viewing chiral carbons, chiral compounds, and meso molecules. Even though the Fischer projection can be quite challenging, it can also be the … Continue reading If H Is on the Horizontal…Then It’s Horribly Wrong

It’s All in the Arrows

In organic chemistry, I find that arrows are critical to teach organic content in a mechanistic perspective because they tell the story of all organic transformations. I try to impress upon my students that the arrows in mechanisms can provide a clear indication of how to move electrons. Mechanistically, students struggle with knowing the difference … Continue reading It’s All in the Arrows

Rules of Thumb

Nearly every semester, I am asked a question that I’ve never been asked before. I have found that by giving students some rules of thumb (ROTs), I can help them understand the basics while also giving them specific strategies for solving organic chemistry problems. More recently, I’ve recognized that the mechanistic organization helps enforce my … Continue reading Rules of Thumb

Mechanism Problems with Numerous Teaching Moments

Each year, as my students complete Chapter 8, I find tremendous value in assigning a handful of written mechanism problems that not only challenge students, but also reinforce important lessons about mechanisms that we learned throughout Chapters 7 and 8. This year, I assigned the following two mechanism problems (not found in Chapter 7 or … Continue reading Mechanism Problems with Numerous Teaching Moments

The Far-Reaching Benefits of Teaching Organic Chemistry According to Mechanism

In my experience, the traditional method of teaching organic chemistry courses according to functional group often leads students to rely on memorization. For example, a single chapter on alkyl halides may include substitution reactions, radical reactions, and additions to alkenes. With such a large volume of information, it’s very difficult for students to manage and … Continue reading The Far-Reaching Benefits of Teaching Organic Chemistry According to Mechanism

Ballroom Dancing as a Metaphor for Learning Organic Chemistry

Students are notorious for feeling overwhelmed by the subject of organic chemistry. This leaves the instructor perplexed with the thought of effectively and adequately teaching the course. Often, the question posed is … "…to use or not to use reactions?" Both as a student and as an instructor, I have heard that students only feel … Continue reading Ballroom Dancing as a Metaphor for Learning Organic Chemistry

Squarecap Is a Game Changer in My Flipped Classroom

Years ago, I switched to teaching a flipped classroom and using a classroom response system (aka CRS or clickers). In this format, my students are assigned to read about a dozen pages from the textbook before coming to class. At the start of class, I assign a problem to solve that is based on the … Continue reading Squarecap Is a Game Changer in My Flipped Classroom

Cis-trans isomerism: A valuable litmus test for things to come

Every time I teach Section 3.9, which covers rotations about single and double bonds and cis/trans isomerism, I’m reminded of how valuable an exercise it is to have students determine whether a particular double bond can have cis/trans configurations possible. It may not immediately jump out at you as a valuable exercise, but consider this. … Continue reading Cis-trans isomerism: A valuable litmus test for things to come

Proton Transfer Reactions and Thinking Like a Chemist

Teaching students how to think like a chemist is a challenging, but necessary feature of any organic chemistry course. A seemingly simple question such as, “How will these two compounds react when I mix them?” can stump even the best students. Since it is impossible to memorize every possible reaction combination, students must rely on … Continue reading Proton Transfer Reactions and Thinking Like a Chemist