Adventures in Undergrad Chemistry 1: General Chemistry

To celebrate acceptance of my abstract at BCCE 2024 in Lexington, I thought I’d get some of my experiences from undergrad chemistry at Kentucky down on paper. In a sense, I never really left college (just moved to “the other side of the desk”), so many of those experiences have stuck with me over the years. Read on for a taste of chemical education in the 2000s!

My first chemistry course at Kentucky was General Chemistry II in Fall 2004 with Harriet Ades, an aged Jewish woman who, in retrospect, had clearly been worn down by years of teaching obnoxiously large courses. I didn’t take AP Chemistry, but Kentucky ran a placement test that gave credit for General Chemistry I, and I managed to pass it. Thanks to the dual advantages of chemistry running in the family and my being motivated to impress a girl, I applied myself pretty hard in high school chemistry and it paid off.

Ades’s course was my first exposure to a large college STEM classroom. My memory’s a little fuzzy, but I believe she used transparencies and an overhead projector—there were no smart boards or touch screens yet in 2004. Her lectures were mostly bland, although on very rare occasions she would get excited. We lived for those moments!

The thing I remember most from that course is the textbook. I had a floppy paperback version of the eighth edition of Chang with an electrostatic potential map on the cover. The book came with a CD full of videos of worked example problems by a company called Thinkwell, in the “document camera + talking head” style of Tyler DeWitt. Those videos were great! At the time, I think I figured the presenters were actors, or maybe high school chemistry teachers. Years later, doing work for Organic Reactions, I came across an eerily familiar author photo and realized that one of those presenters was organometallic chemistry professor Dean Harman! (Now I know better—publishers use faculty in these things because they know we’d make those videos for free.) Never did figure out who the Asian guy was, though.

I bring up the textbook and videos because they spurred me to adopt the dubious policy of attending every other class and using the book to fill in the gaps. Every day after I attended that class, I would drink a Dr. Pepper out of the vending machine in the Chemistry-Physics Building. (My diet in college could be a post unto itself—long live K Lair.) By the middle of the term, I had developed a distinctive shake in my hands before I “got my Dr. Pepper” for the day. Probably spent a good bit of time in that class thinking about the upcoming caffeine hit anyway. On my “days off,” I realized I could spend a half hour reading and taking notes on the textbook instead of an hour sitting in class. Thirty minutes of freedom!

I also remember making the conscious decision not to learn how to calculate the pH of a buffer after addition of strong acid or base to it. That was another highly questionable example of college “strategery.” That course used multiple-choice exams and I was comfortable applying the Henderson-Hasselbalch equation to determine the pH of a buffer. I also understood The Big IdeaTM of buffers that strong acid and base don’t change their pH much. Logically then, in a question asking for the pH of a buffer solution after the addition of strong acid or base, the correct answer is most likely the answer choice closest to (but not equal to!) the original pH of the buffer. In the event of an overwhelmed buffer or several close values, I told myself I was just going to guess and take the hit! I don’t regret the decision—it maximized my happiness at the time—but I do use it as a cautionary tale for students and to encourage them to at least engage in metacognition.

My first and only General Chemistry Laboratory course was in Spring 2005, bright and early at 8:00 am. Thankfully, I was blessed with an extremely peppy lab partner who never failed to shake me out of sleep. True to form, she tracked me down years later to try to rope me into a multi-level marketing scheme. (Yes, I went to the meeting. Yes, because she was a girl. Yes, I regret it.) Our TA was a well-meaning but inept international graduate student; my lab partner derived endless joy from messing with him, not so much in a spiteful or mean way, but in the spirit of initiating him into her version of “American college culture.” That’s about all I remember from that lab, as whatever lab reports I put together are lost to the sands of time.

I feel like students often don’t appreciate how important those first couple of semesters are in establishing the life habits and study habits they’ll carry through college and even their future careers. I carved out time every day to run in the late afternoon—back then, the Johnson Center was brand new—and I still try to run at least once a week. My diet was crap and remained crap until having kids (eight years later!) basically forced me to become a passable cook. The silver lining of the “attend every other class” policy was that I figured out that, at least in chemistry, my learning (1) was up to me, not the professor and (2) could usually happen more efficiently outside of class by reading and taking notes than in class. Lectures and YouTube videos are less efficient than reading, gang!

Next up, I’ll dig into my sophomore year and my organic chemistry experience. Stay tuned!

The Wildest Carbon You’ve Seen This Month

Reproducibility problems in organic chemistry have a long and storied history. Recently in Nature, Frank Glorius and co. provided a fresh set of recommendations to address the issue; that paper is worth a read.

One resource we can generally count on for reliable experimental information is Organic Syntheses. Org Syn procedures are extremely detailed, include photos (a surprisingly recent requirement), and are checked by editor’s labs. These are the cream of the crop of organic reactions, which means they can be boring and pedestrian at times. Cynical readers will quickly appreciate why flashy-looking reactions don’t often find their way into Org Syn…

Lately however, some super cool reactions have appeared in the pages of this journal. Take this reaction from the Alcarazo group at Göttingen. Starting from dibenzothiophene S-oxide, the authors synthesize an intriguing thiophenium-substituted diazoacetate ester via triflation and nucleophilic substitution at sulfur.

I feel like triflic anhydride can turn anything into an electrophile.

The way the diazo group is commonly drawn has always bugged me a little. It’s easy to forget that diazoacetates can be thought of as “alpha-diazonium enolates”—hence their nucleophilic character at the diazo carbon.

The diazo carbon in the product is even stranger, with a linked sulfur having formal positive charge. Now the structure looks like a “diazonium-substituted sulfonium ylide,” too! Take a guess of the chemical shift of that carbon. NMRdb puts it at about 70 ppm—way upfield of an alkene carbon but not exactly in carbanion territory.

So many resonance forms…!

The Count of the Floor Dogs (Happy Pi Day!)

On this most mathematical of days, let’s take a look at one of the most fascinating ways to calculate π, 3.1415926535…

Georges-Louis Leclerc, also known as Count Buffon, was an eighteenth-century French nobleman with a penchant for learning and research. He is credited with a delightfully elegant “experiment” that, when taken to its limit, produces the value of π. Yellow Jackets Against Computer Programming, a student organization here at Georgia Tech, did their own twenty-first century version of this experiment today on Tech Green.

The rules of the game are simple. We start with a massive vat of hot dogs (okay, Buffon used needles) of length a and a floor with an infinite number of equally spaced lines or cracks separated by a distance b. We begin throwing the hot dogs randomly at the floor, keeping track of the number of times a hot dog crosses a line (“hits” h) relative to the total number of dogs thrown (“throws” T). The ratio h/T is the measured probability p that a hot dog crosses a crack. The question is, what is the theoretical value of p after an infinite number of throws? You can play around with the experiment and simulate it yourself here.

We can simplify the problem by recognizing that we only need to look at the space between two adjacent cracks and focusing on short hot dogs with a ≤ b. The position and orientation of the dog can be parametrized using the distance of the dog center from the closest crack (0 < x < b/2) and the acute angle formed by the dog and either of the cracks (0 < θ < π/2). (This assumes perfectly linear and rigid hot dogs.) The total number of possible orientations can be represented as a double integral.

For a short dog with a ≤ b, a hit will only occur if x is less than or equal to (a/2) sin θ. Over all possible angles then, the number of hits is yet another double integral.

After those fun little exercises in integration, the probability of a hot dog hitting a crack is gravy.

However, a, b, and the probability p are measurable if we can get our hands on a vat of hot dogs, a ruler, and a floor with evenly spaced cracks. This means we can approximate π by throwing a large number of hot dogs on a floor with known a and b.

Although our Monte Carlo sampling approach will only approximate the integrals above, as we throw more and more hot dogs we are guaranteed to get closer and closer to the theoretical value of p. As a result, we will also get closer and closer to the value of π.

Buffon’s experiment can be taken even farther by bolting hot dogs together, using circular dogs, and more. For a great exposition of the problem, those extensions, and some of the implications for current research, check out this statistical mechanics course on Coursera (specifically, week 10). The case of a hot dog longer than the distance between two cracks, which is somewhat more complicated than the short-dog case due to the possibility of more than one hit, is discussed in the Wikipedia article for the problem.

Reading the Chemical Education Literature Between the Lines

Seymour and Hewitt (1)…found that 90% of the students who switched out of STEM majors and 74% of those who persisted in STEM majors identified “poor quality STEM teaching” as the most common concern…These findings highlight a need for transforming students’ learning experiences in postsecondary level STEM courses, particularly in introductory courses, to improve student outcomes and retention.

Stains, M. et al. J. Chem. Educ. 2024, ASAP. (link)

The passage above appeared in the abstract of a recently published Journal of Chemical Education article titled “A National Snapshot of Introductory Chemistry Instructors and Their Instructional Practices.” This important paper, for which yours truly was just an infinitesimal data point, describes the demographics, training, and practical characteristics of introductory chemistry instructors in the United States. The major findings?

  1. Most instructors of introductory chemistry are white males of European descent with minimal training in teaching. After being hired, most faculty receive only very short informal training (one-off workshops and the like).
  2. While most instructors are aware of active-learning strategies for teaching, lecturing remains the predominant instructional practice, particularly when examining how class time is actually used.

Nothing too surprising here. The paper includes all kinds of other interesting results as well, such as statistics on the number of decision makers associated with various aspects of course design: textbook, content covered, exams, and instructional methods. It’s absolutely worth a read as a descriptive snapshot of introductory chemistry instruction in the second decade of the twenty-first century.

What we do or recommend with these results in a prescriptive sense is a whole other can of worms…and the recommendations often don’t follow logically from the data. (The older I get, the more this bothers me. I used to resent the old-codger naysayers, but I can feel myself turning into one.) The quote above is representative of the way in which many articles in the STEM education literature try to make the awkward jump from “is” to “ought.” The logic is easy to unpack, if we just try: because 90% of those who switch out of STEM majors cite bad teaching as a major concern, we just need to improve the teaching to keep that 90% in the STEM fold.

But “improved teaching” means different things to these authors, the faculty they surveyed, and the students of those faculty. Increased instructor charisma and entertainment value—changes that students would view as an improvement—will lower that “poor quality teaching” statistic significantly without improving the retention rate of STEM majors. Charismatic instructors with high standards can create “sticker shock” for students looking at their grades (ask me how I know). On the other hand, making exams easier will cause an increase in retention without an objective decrease in “poor quality teaching,” despite what student course evaluations might say. In any event, this isn’t what the authors mean by “improved teaching.” They want more active learning and research-based instructional strategies (RBIS) in the classroom. The assumption here (really the definition of “research based”) is that, with no change to assessments, greater RBIS leads to improved student performance and improved retention.

Practitioners of teaching have to ask the “but does it?” question here. Fundamental questions about the underlying research abound: what about the Heraclitean effect of never being able to give the same exam to the same group of students twice? In surveys of perceptions of learning, what about response biases? Old codgers often frame these questions as excuses to continue doing things the way they’ve always done them. I don’t want to do that here—there is no question that some amount of active learning is beneficial—but I do want to call attention to some of the more legitimate reasons why the faculty surveyed may not be using active learning in introductory chemistry as much as the research community would like. (That the research community benefits from being a bunch of Chicken Littles re: the state of chemical education is a post for another day, but this undoubtedly plays a role in the tone of CER papers: “please fund my research.”)

Imagine, if you will, a classroom built entirely on active learning. In the first thirty seconds, the instructor says hello to the class; in the remaining forty-nine minutes and thirty seconds, students are working through structured activities under the guidance of the instructor and learning assistants. No explanation lasts longer than two minutes. There is no motivating introduction to the day’s topic, no conveyance to the collective of the instructor’s passion for the subject, no summary at the end of what’s been accomplished. And the students are busting ass!

The environment in our hypothetical classroom is as one sided as the most boring traditional lecture (the hyperbole is the point). There’s a rightful sense that students are pulling all the weight and doing all the work. While some would argue that getting students to do the work should be the goal, the instructor isn’t fulfilling his or her social obligations in this classroom. In the vast majority of STEM classrooms, some amount of lecture is part of the social contract. This is, in my eyes, why lecture continues to endure in STEM classrooms, particularly in more advanced courses. Implicitly and sometimes even explicitly, students demand “tell me what I need to know!” and discounting that demand completely isn’t socially realistic.

Then again, fighting against that demand is part of our work in promoting student growth and independent study. Those in the know will throw out a figure of 70% as the “research-based” portion of class time that should be spent on active learning activities in introductory STEM courses. Of course, in practice the ideal number will depend on the social context of the classroom, the day’s topic, the level of the course, the instructor’s personality, and other factors. Most days in my semester-long Organic Chemistry II course, I’m not going to hit that number even if I try, and I’m okay with that.

“Last Four Out” Methods

A thought-provoking tweet here about an undeniably useful synthetic method! The combination of silyl enol ethers and Lewis acid enables alkylations that enolates can only dream of.

The linked paper was the first in a series reporting on the tertiary alkylation of silyl enol ethers by the Reetz group. For example, a subsequent publication showed high levels of retention in reactions of certain tertiary alkyl halides having stereoelectronic or steric biases, such as 7-chloronorbornene. Silyl enol ethers have since enjoyed a long and fruitful period of development as nucleophiles that continues to the present day.

My gut reaction on seeing the tweet was that, if I had 16 weeks to teach an advanced organic chemistry course, this method might be just outside the scope of coverage. In the spirit of March Madness, it’s a “bubble method”—undeniably useful and interesting, but with limited applicability. Sure, we don’t have many methods to make quaternary carbons, but how often is that actually needed? Personally, I’d lean toward a deeper dive into Mukaiyama and Lewis-base-catalyzed aldol reactions of silyl enol ethers, particularly since the products can be taken in more directions.

All that said, this is a tough choice. We have to make these kinds of tough coverage choices all the time in chemistry. There’s just too much known out there. Is it useful to know that we can use tertiary alkyl halides in alpha-functionalizations of carbonyls? Sure. But “knowing we can” often isn’t worth pointing out in an academic setting, particularly as that knowledge is just a web search away. Instructional value is more than just “knowing we can.”

The Synthetic Machete 2: Fun with Internal Redox Chemistry

Bakke, J. et al. Acta Chem. Scand. 1972, 26, 355. (link)

Last year, I described reactions that shave several steps off a synthesis as synthetic machetes. The idea is that these reactions cut through the thicket of manipulations sometimes needed to get a target just so: add a protecting group here, interchange a functional group there, oxidize this, reduce that, etc. A synthetic machete recently showed up on r/chemistry: the conversion of o-nitrotoluene to anthranilic acid via formal oxidation of the methyl group and reduction of the nitro group. A nifty reaction, to be sure—instead of oxidizing the methyl group and then reducing the nitro group (or vice versa) in two steps, both the oxidation and reduction can be made to occur in one step, apparently internally.

An interesting and potentially useful rearrangement!

The first comment on the Reddit post took the typical teacher angle of “you can’t do that”—you have to oxidize first and then reduce. Hordes of Organic Chemistry II students (and instructors!) would agree. However, the noble teacher was then immediately well actuallyed by a commenter who pointed to an Acta Chem. Scand. paper reporting on the reaction. Sure enough, treatment of o-nitrotoluene with sodium hydroxide in ethanol yields anthranilic acid. Why don’t we teach this stuff?!

Well, the devil’s in the details with this one. The abstract, where the big flex is supposed to be, reports a whopping 13% yield of anthranilic acid. In the teacher-commenter’s further defense, they did suggest just…ya know…buying anthranilic acid. That would probably be cheaper and faster than trying to run this reaction. It’s a reaction to keep in mind for that post-apocalyptic fantasy world in which you’re the only chemist left in the city, but not one that will knock people’s socks off with its utility in the world we actually inhabit.

The mechanism of the reaction is a potential head-scratcher. Deprotonation of the methyl group in 2-nitrotoluene by hydroxide seems plausible (at least reversibly). The resulting anion contains an electrophilic carbon poised beautifully to be attacked by a newly negative oxygen atom. That’s one C–O bond down! Proton transfer back to the remaining anionic oxygen sets up a structure in which water can be eliminated to form a long conjugated system. E2 elimination with hydroxide as the base does that job.

A plausible mechanism, although the final two proton transfers may come before the last elimination step.

Interestingly, this elimination makes the same carbon electrophilic again. Now, hydroxide adds there to establish yet another C–O bond. Following proton transfer, another elimination occurs to establish the C=O pi bond. This may occur after proton transfers set up an N+/O– zwitterionic intermediate, but I’ve drawn it in the neutral structure with proton transfers occurring afterwards. The zwitterion may well be more plausible, though.

With subpar yield and minimal scope, this synthetic machete is little more than a mechanistic curiosity. It’s a case of “too good to be true”!

“Friedel-Crafty” Reactions with Chloroacetone

Zaheer, S. H. et al. J. Chem. Soc. 1954, 3360. (link)

Friedel-Crafts alkylations and acylations are staple reactions of Organic Chemistry II. After alkylation is introduced, its tendencies for rearrangement and polyalkylation are usually pointed out to motivate the Friedel-Crafts acylation. Acylium ions, as a rule, don’t rearrange. But are there electrophiles other than acyl chlorides with built-in “anti-rearrangement” structures? For example, consider an alkyl halide with unsaturation in the α-position such as chloroacetone. Although rearrangement with loss of chloride, giving ethylacylium cation, seems feasible, it’s unclear how rapid such a rearrangement would be. Migration of C(sp2)—C(sp3) bonds is not common and is virtually absent from the typical reactions of Organic Chemistry II. Could we have stumbled upon a useful Friedel-Crafts alkylation with a primary alkyl halide electrophile, sans rearrangement?!

Will chloroacetone participate in Friedel-Crafts reactions without rearrangement?

A student reviewing for our first exam in CHEM 2312 proposed this idea. On paper at an introductory level, it looks good, but on a practical level it looked suspicious (sus?) to me. Chloroacetone is a heck of an electrophile, with two electron-poor carbons directly linked to one another. (It’s so electrophilic it was used as tear gas in World War I. Thanks Wikipedia.) The ketone carbonyl carbon could very well get involved in the reaction, perhaps even before the alkyl halide, especially in the presence of a Lewis or Brønsted acid. I just had to find out the end to this story, so I dusted off the ol’ Google Scholar and, rather surprisingly, quickly found this paper describing the reactivity of α-haloketones with arenes in the presence of Brønsted and Lewis acids.

When combined with a Brønsted or Lewis acid, chloroacetone and arenes condense to form α-methylstilbenes.

Regardless of the acidic promoter, these investigators observed the formation of α-methylstilbenes when phenol, anisole, and phenetole were treated with chloroacetone. Two molecules of the arene condense with chloroacetone with the loss of HCl and H2O. The mechanistic possibilities are intriguing…

In an earlier publication, Bhargava and Zaheer postulated that an initial Friedel-Crafts alkylation was followed by addition of a second molecule of arene to the ketone. Dehydration then established the alkene in the product.

Alkylation-addition-dehydration mechanism proposed by Zaheer in April 1953.

They later revised this proposal and suggested that two molecules of arene displace the carbonyl oxygen first, and then rearrangement and dehydrohalogenation occur.

A second mechanistic proposal put forth by Zaheer in November 1953 invokes double addition of the arene to the carbonyl carbon followed by rearrangement and dehydrohalogenation.

It’s interesting to speculate whether a phenonium ion is involved here, although this work was carried out before the detailed work of Olah and others on these kinds of carbocations. Phenonium ions are essentially spiro arenium ions derived from addition of phenyl cations to alkenes or ionization of 1-halo-2-arylethanes. The structural elements are present in the first intermediate above for phenonium formation; loss of a proton would then give the product stilbene.

One plausible mechanism involve a phenonium ion intermediate.

The stereoelectronics of that elimination do look a little odd; opening of the ion to a tertiary benzylic cation also seems plausible and is consistent with Zaheer’s later proposal (note the tertiary benzylic chloride, which likely came from this benzylic cation). A more recent study indicates that formation of styrenes from phenoniums is generally a minor pathway…but the additional benzene ring could change this!

Small Molecules Doing Big Things: Mavacamten

Wikipedia is never too far away when I’m watching television. Whenever a pharmaceutical commercial comes on, I’ll leap up and grab my phone to frantically search for whatever alphabet soup of a name Merck’s marketing department has chosen for their latest shot. Or, more often than not, I’ll squint or move in closer to the TV to get a good look at the chemical name. A name ending in “-ib” or “-ab” is a dead giveaway for an antibody, but there’s still quite a market for small-molecule drugs out there with relevance to the not-so-biochemically-inclined organic chemist! The latest to catch my eye is mavacamten, which BMS is marketing as Camzyos (a very Final-Fantasy-boss-sounding name, if you ask me).

Where do they get these names? Throwing darts at a Ouija board?

Medicinal chemists love heterocycles…often because the heterocycles love them back. The magic of aromaticity means that condensation reactions to form heteroarenes often work fantastically well. Plus, the pieces can be varied structurally to create a broad library of candidate compounds. Rings can be made though annulation reactions or bought and functionalized using cross coupling or SNAr.

This particular heterocyclic compound is used to treat pathological thickening of the heart muscles and its mechanism of action is delightfully simple (for the molecularly minded): it inhibits the activity of cardiac myosin through allosteric binding, causing the heart muscles to relax. As mavacamten is the first drug to target this deep biochemical mechanism for muscle tightening, I have a feeling we’re at the beginning of a long and beautiful story.

How the compound is made is a much shorter but no less beautiful story. The structure is reminiscent of uracil, with an extra bit of oxidation at the carbon linked to the benzylamino moiety. It feels right to install that amino group last in the synthesis using SNAr, as it’s the only bit of chirality in the molecule. This gets us back to a chlorine-substituted pyrimidine-2,4-dione, which can be made from the 2,4,6-trione using phosphorus oxychloride (a positively magical reagent that every medicinal chemist should be aware of).

Retrosynthesis of mavacamten.

There is a hint of symmetry in the trione that suggests an efficient preparation of the ring. If we pretend the isopropyl group isn’t there, the molecule has a plane of symmetry cutting right through it. The combination of urea with a malonate ester would forge the ring beautifully via [3 + 3], “AA + BB”-type annulation. Since the ester groups in the malonate are equivalent, we can just use N-isopropylurea to make the exact product we want. Two amides, one flask!

Synthesis of mavacamten. More details can be found in a 2021 patent by MyoKardia, Inc.

THINK! and Other Helpful Advice from College Professors

One of my organic chemistry professors who couldn’t stand silence used to yell THINK! at us after he asked a question, if the room stayed quiet for long enough. I often felt a little pang of resentment—I am thinking; the problem is that I don’t know! I’m not confident that the basic premises on which my understanding of chemistry is based are robust and correct enough to answer the question correctly—or even incorrectly in a not embarrassing way!

In retrospect, THINK! was less aimed at eliciting a correct response than designed to set our neurons in motion doing something, the way one would command a dog to LIE DOWN! or SIT! He wanted chemical reasoning to become a kind of automatic Pavlovian response to chemical questions, thinking ahead to moments when such questions would come up in our future careers or lives. As the inimitable Wes Mantooth laments in Anchorman, “even the guy who can’t think says something…come on!”

It’s a testament to a belief I’ve observed in many teachers over the years, that trying to reason is better than just staring slack-jawed at a problem until someone with more expertise (or just someone louder…) steps in. Eventually that extra “someone” will disappear, as you’ll be working on a problem so new, so esoteric, or so big that there is no “someone” with more expertise. The teachers are right, aren’t they? Everyone speaking up and being wrong, but slowly refining the collective understanding over time, is better than no one saying anything.

Thoughts on the Republican Primaries and Trump

My seven-year-old son recently asked about former American Presidents who are still alive. My wife and I rattled off the list in reverse-chronological order: Carter, Clinton, Dubya, Obama…and then we reached He-who-must-not-be-named. There was strain, particularly for my wife, in having to acknowledge “ownership” of the fact that Donald Trump served as POTUS from 2016 to 2020. Although we could claim having done all we could by not voting for him, the thought that Trump represented our country to the rest of the world for four years was disgusting, shameful, and rage inducing. Such feelings tend to energize me (with predictably problematic results…), and so I launched into a bombastic “teacher-mode” speech about how we have to break the Voldemort-esque hold the idea of this man has over our minds. His deeds and nature have to be named and explored, as hard as that might be. Speaking embarrassing truths takes courage but is the only way to prevent destructive fantasies from enveloping us.

My wife likes to remind me that these highfalutin speeches are lost on a second grader. She’s probably right. It’s right there with “the university will run without you,” “pick your battles,” and all the other things she tells me to stop unproductive rants. This is, however, one of those times when I feel I cannot be silent; as a matter of personal morality and self-respect, I feel I have to articulate why you—each and every voting American, no matter your hometown, race, gender, or creed—should not vote for Donald Trump in the 2024 Republican primaries or general election.

It’s easy to write off these arguments based on the my position and background. What’s the catch? What do I have to gain by writing this? I can’t keep you from asking those questions. All I can do is try to make the best argument I can, while being transparent about where I live—inside the city limits of a major American city—and where I’m at economically—doing fine, in an education job that is extremely stable with a wife in healthcare in a similar situation. If you want to write off my argument as the ramblings of a rich urbanite, or you just came here expecting chemistry or chess, feel free to stop reading now. I can’t stop you. However, I don’t think my take is the prevailing narrative and I think it’s one that can appeal to everyone…yes, even those who’d like to close our borders!

As of January 15, 2024, Trump appears highly likely to win a plurality of votes in the Iowa caucuses. The margin of victory will likely be large, but this is only because of a remarkable lack of challengers. To me, someone who gives a cursory once-over to the Atlanta Journal-Constitution and Wall Street Journal every morning over coffee, it looks like the GOP has been eating itself since 2016. Republicans in Congress have used denial as an excuse for doing nothing, which has led to thin resumés, which has led to an embarrassingly thin field of candidates. All this to placate a minority of Americans who want Trump to be the face of the GOP.

My issue with this situation is not the Trumpian agenda of exclusion, hate, and ignorant populism. Of course I don’t agree with it and this is why I would never vote for the man personally as a matter of self-respect. But my personal take, for all the “rich urbanite author” reasons outlined above, will not convince anyone who is going to vote in the Iowa caucuses—or the Georgia primary, for that matter—not to vote for Donald Trump. My argument is that Trump had a shot and his problems as President are now a matter of public record. The problems are that he is (1) ineffective in executing laws (i.e. his would-be job as President) and (2) an “empty vessel” and mouthpiece for God-knows-who. Both issues should be extremely concerning for all Americans.

I’ll start with the mouthpiece bit. This is obvious and has been for decades: Trump will say and do whatever is necessary to save his own skin and line his pockets. Savvy groups of people—anyone from a nation to an NGO—can and have played him by taking advantage of his insane penchant for self-preservation. I believe many conservative groups think they can work this to their advantage, but there was so much of it from 2016 to 2020 that the result felt incoherent. However, the actions of a few groups, such as Russia, likely had very damaging effects. The damage to the United Nations, now completely unable to stop Russia and Israel despite an international consensus against both, started then and is only being felt now.

Maybe you hold onto the idea that, in following Trump, he will listen to you and promote your personal political philosophy, whatever it might be. The problem is, you have no power as an individual. Trump and his advisors are highly sensitive to this fact. You cannot help him line his pockets and so he spouts words that pay lip service to your views without backing them up with action. Your collective, which shares your views, doesn’t even have enough power for him to take real action. He believes that talking out of both sides of his mouth will enrich him most, promising without delivering.

Regardless of your political views, this is the most reasonable conclusion that can be drawn from 2016 – 2020. Yes, the country took several steps backwards. But things didn’t fall apart, because our country lumbered on its capitalist way at a much more humdrum pace than Trump’s rhetoric suggested. All talk and very little action, except the hate he inspired by existing in the office of POTUS—which was very dangerous in its own right (January 6 comes to mind) but probably unconvincing to a farmer in Iowa, for whom life changed little in those four short years. We all still went to work, worked hard, and sent our taxes to Washington.

This brings me to Trump’s ineptitude as a President, which should be very concerning to anyone who looks for leadership from that office. From my point of view, no meaningful federal legislation was introduced between 2016 and 2020. It should be borne in mind that I was busy raising my first kid, born four months before Trump took office, but even so…the Trump administration introduced no meaningful legislation to Congress in four years. Denial, evasion, and kicking the can down the road took the place of tackling the real problems facing our country.

We Americans do love denial. Problems? Grab a beer and watch football. Angry? Head to the gym and pump the pain away. But it is the job of government officials to face and address our nation’s problems, or at least argue for how we’re currently dealing with them. (Obama, in my mind, was great at cogently arguing for the status quo.) Trump did neither.

The President will almost certainly have little direct effect on your life. Whether you’re a rural farmer or an urban executive, in this massive country, it’s easy to ignore our government and focus on our little corner of things. Obama made this easier for me and I have no doubt that Trump made it easier for many conservatives. But we have to be wary of those feelings as a society and continue to pay attention. At the very least, we have to acknowledge that someone like Nikki Haley or even (ick) Ron DeSantis would do a better job as President than Trump would…and has!