School

A Course in Organic Chemistry Doesn’t Need to Be a Living Hell

A veteran instructor swears he could teach it to anyone—given time.

People in white lab coats put materials into a test tube.
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Earlier this week, the New York Times covered the dismissal of longtime and highly decorated professor Maitland Jones Jr. from his position as contract (non-tenured) faculty teaching a large organic chemistry course at New York University. Following the receipt of a student petition that said the class was too hard to pass, Jones was not accessible as an instructor, and the students’ future chances at going to medical school were being put at risk, administrators dismissed Jones, citing low student evaluation scores—even though his dismissal was not a remedy sought by students in the petition.

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The resulting online discussion was like a game of Clue, with people trying to figure out who was to blame for the outcome.

It was the aging professor, with his old-fashioned ways, in the lecture hall.

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It was the whiny students, with the petition to the director of undergraduate studies, in the departmental office.

It was the administration, with their craven pursuit of tuition dollars, at the treasurer’s.

Having had a nearly 20-year career as a college writing instructor, and having wrestled with student disengagement of the same kind Jones reported seeing among his students at NYU, I suspected there’s likely something to be learned by examining this problem at a structural and systemic level.

Unfortunately, I know squat about organic chemistry. I took earth science in college and didn’t cover myself in glory, even in that easier course. So I reached out to Dan Singleton, professor of chemistry and Davidson professor of science at Texas A&M University, where he has been teaching organic chemistry at the undergraduate and graduate level for 35 years. At Texas A&M, Singleton has been honored by the Association of Former Students with distinguished teaching awards in 1995, 2008, and 2015, and in 2017, he received the Wells-Fargo Honors Faculty Mentor Award.

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Singleton and I chatted over email, and I got the chance to ask him what makes organic chemistry hard for students, how doctors find it useful, and whether “weed-out” courses are a net good for education. Our conversation has been edited and condensed for clarity.

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John Warner: First, there’s one burning question that I think people are dying to know the answer to. Should we be referring to organic chemistry as “o-chem,” or “org chem,” or “orgo”? Also, for those of us who only know organic chemistry as that thing we did our best to avoid while in school, what is it? How do you describe it to a layperson?

Dan Singleton: I hear “orgo” mainly, these days, but maybe that is just because it stands out to my ears. “O-chem” is what I grew up on.

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O-chem, the study of organic compounds, is special because carbon is the ultimate Lego of atoms. It hooks strongly to itself in chains and rings and layers, it forms strong connections with almost any other atom, and you can build things limited only by your creativity. Life exists because the chemistry of carbon compounds, organic chemistry, allows an infinite and controlled complexity of structure and function.

There seems to be near universal agreement that organic chemistry is “hard.” What makes it so hard?

It shouldn’t be hard. Look, o-chem isn’t that deep, and it doesn’t require complex skills coming in the door. In 35 years, I have never once said to a student “If you had learned more in X class, o-chem would be going better for you.”

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But o-chem causes problems for students in two ways. First, students are used to courses where they have seen much of the material before. Each course is partially review, with a bit of an advance each year. Students taking gen chem in college may be seeing much of the material for the third time. O-chem is all new. Not a single student comes in knowing how to push electrons for an SN2 reaction or how to draw the chair conformations for trans-1,3-dimethylcyclohexane. After the first week, every bit is outside of their comfort zone.

The second issue is that the course is mercilessly cumulative. If you have trouble seeing resonance structures in Week 2, acidity is going to roll you over and over. Miss a reaction in Week 7, and you won’t know you can use it in a synthesis in Week 10. Fall behind and the lectures become harder and harder to understand. You can’t make up for it by cramming a couple of days before an exam.

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On Twitter, you said that you could teach anyone organic chemistry, given enough time. But I feel like this would be a steep challenge for, well, someone like me with no science background, limited technical knowledge of any kind, and no apparent facility for spatial reasoning. How would you reach me?

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I don’t need for you to know anything; I don’t assume that my class walks in with any useful skills. Much of what they do know is simplistic or wrong or off-focus for the course, or most often just too slow. Their ability to write a Lewis structure and assign charges in two minutes is no advantage over your not being able to do it at all. I will teach you the quick and dirty way, just like I do them.

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I would reach you by hunting you down and making you do problems, in class, online, in problem sessions, in problem sets and from old exams. Then when your arrows go wrong, when your equatorial bonds go astray, as they will, we fix them, curved arrow by curved arrow, charge by charge. You might not need all that feedback—a portion of students, a small portion, hear once “Start every arrow at a lone pair or a bond, don’t push atoms, don’t push positive charges,” and never make those mistakes again. Some need to go wrong and have it corrected a couple of times, some five, some 10, some 20—whatever it takes. If we can get you a few bottleneck skills, undergraduate o-chem devolves to details, nontrivial but more like a biology or history class.

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My field is teaching writing, and one of my consistent refrains about how we teach writing is that we really know quite a lot about what works to help students improve as writers, but the systems we teach and learn inside of are largely hostile to doing the things we know are effective. Most teachers have too many students to work with closely to give the kind of feedback that helps students progress. First-year writing courses are often taught by grad students who are dedicated, but lack experience, or contingent faculty, who are busy trying to cobble together a reasonable living. It makes doing what we know works very difficult.

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I suppose this is a long way of asking about the structural conditions of teaching organic chemistry. What are the conditions? Are they sufficient to do the work?

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The situation seems the same in organic chemistry. We know what works—working problems with feedback. That takes time, which takes both university resources and the students being able to take advantage of those resources. My university surely tries—we have a long-term commitment to relatively small classes, maxed at ~100, with each having an extra supplemental instruction leader and with the instructors holding extra problem sessions. But we know it isn’t enough, because we lose about 20 percent of our organic chemistry I students as DFQs (people who get D’s and F’s, or who drop the class). That is too many. I think we could save half of those without lowering standards, but getting students the required one-on-one interaction and feedback is harder and harder with larger classes. I have been teaching a small honors class in an experimental way, and what worked smoothly for 20 students is on edge at 35, and is largely impossible in a class I am subbing with 67 students. You just can’t get to everyone or catch all the errors.

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But we should never separate entirely a discussion of resources from a discussion of students’ ability to take advantage of those resources. Profs tend to complain about students not coming to office hours or problem sessions, but many are taking a full load and working long hours to survive or at times support their families. Courses like o-chem are really hard for those students, and it is a problem with our system.

I want to ask about organic chemistry and its status as a so-called weed-out course, particularly for medical school. I’m curious about your feelings about this concept of weed outs? Good thing? Bad thing? Some mix of both?

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I don’t like the idea of any course being a weed out, because we should surely consider people in a holistic way. Also, there is no reason to view the subject matter of organic chemistry as being particularly important for medical school, though I will defend it being of some value.

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But with that said, I will perhaps get myself in trouble by saying that o-chem success is worthy of careful consideration. O-chem is the first course that many students take where being a rich child who has had every prior advantage and the very best preparation is of little help; being lazy but very bright won’t cut it; falling behind, then cramming, is a sure recipe for doom.

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O-chem can’t equalize everything—as we said above, having the time and ability to get help comes with privilege, and we can’t get away from it entirely—but I suspect it is a fairer measure of students than gen chem or calculus or composition, all of which will be greatly influenced by their high school. So the lore is that the organic chemistry grade is the best indicator of how someone will succeed in the first two years of medical school.

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Is organic chemistry truly vital for future medical students who then become medical doctors? If so, in what way?

We just went through a pandemic where nonsense and pseudoscience were rampant and killing people, and they still are, and I think the only thing that saved us as a society was that you could say to people “Talk to your doctor.” Their doctors are the only scientifically trained and trusted authority that most people know. There were obvious exceptions, but doctors held us together. With social media blasting that Paxlovid and ivermectin were the same thing, you could at least rely on no doctors who took organic chemistry thinking so. It would help society if doctors knew even more science, surely not less.

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And you really don’t know any chemistry until you know organic chemistry. At its core, chemistry is about understanding molecular structures and what they can do. You learn that in o-chem. Sure, the details get lost—no non-chemist need ever use or remember a Diels-Alder reaction. But I know from the experience of taking biochemistry before organic that before o-chem so much was just incomprehensible lines on paper. O-chem gives all those lines and letters meaning. The details may be lost more and more over the long run, but the basic ideas remain. I can’t imagine thinking about, say, pharmacology without having learned o-chem.

While not every situation like what’s going on with Jones and the students and administrators at NYU makes the New York Times, in my experience, examples of disconnects between students and a college course are common as dirt. Throw in the complications of the pandemic, and things are even more fraught. Rather than debating about which group is most at fault when these things happen, what should we be doing to bridge these gaps?

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The days of students being passive consumers of whatever kind of course a prof wants to throw at them are gone. They are going to make judgments on courses and broadcast their opinions, and at times it can snowball into a course meltdown. Students can certainly be ridiculous at times, and the evidence is that there is often little correlation between the popularity of a course and its effectiveness, but the students’ opinions can’t be ignored. That is just the lay of the land. Their happiness affects learning in courses all by itself.

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Profs need to do a better job of communicating what they are trying to accomplish in a course. We have wildly differing educational philosophies. Many are deep into personal responsibility—a colleague tells students not to come to his office until they have read the textbook chapter. Me, I don’t know anything about teaching students responsibility. I am trying to teach o-chem, and I am going to drag you kicking and screaming through my problems if need be. Some teach at a minimum level to make the course accessible to everyone; others push everything beyond the students, trying to give them a lofty goal for aspiration. There should be room for all these philosophies at a university, but we need to explain it to the students. Break the fourth wall: “I see it was frustrating, but here is why I asked this question.” Students can be very understanding, and they will buy in and even help you defend against complaints, if they know you have a reason you do what you do.

So I am putting this on the profs. The students are what they are, which is mostly reasonable, and they did a champion job accepting the complications of COVID. We can do better.

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