ChemBark

Yes, you read that title correctly: Jean-Luc Picard, the greatest starship captain of all-time, failed organic chemistry at Starfleet Academy. In his defense, it was probably less to do with intelligence and more to do with being distracted:

I pulled that video clip so I can show it to my students during our opening lecture. It should go well with the “How to Win Orgo” handout.

Update (5/1): Thanks to a tip in the comments from “bad wolf”, I went and pulled a clip from Star Trek: Generations where it is revealed that one of Picard’s ancestors won the Nobel Prize in Chemistry. It makes his failure in orgo all the more astonishing.

Here are some nice reads to get you depressed about a career in academia.

1) Last week, The Crimson published a wonderfully deep look into the process of getting tenure at Harvard.

“The ad hoc process is greatly shrouded in mystery; remarkably little is written about it,” says current Senior Vice Provost for Faculty Diversity and Development Judith D. Singer. She smirks wryly as she swigs coffee from her mug, as if this is something she’s explained a hundred times before.

“What the ad hoc process does is it takes a recommendation that has come up out of a department, been through a dean, and says, ‘Let’s look at this with a fresh set of eyes. Let’s look at the totality of the evidence and make a dispassionate decision about whether the recommendations that have come up are really in the best interest of the University,’” says Singer.

In addition to the dossiers and area experts, the committee brings in a set of witnesses from the candidate’s department, typically the department chair and the chair of the committee that did the promotion review, among others. As the witnesses arrive at half-hour intervals, they see the membership of the committee for the first time. Until that point, the identities of the panel—except, of course, those who are ex officio—are kept confidential to prevent advance solicitation.

and…

The cases are rarely cut and dry. Negative witnesses are often called in to dissent the promotion. “Even in a canonization there’s a devil’s advocate,” says Singer, “and that’s part of what the ad hoc process is designed to do: to raise all of the questions and say, ‘Are they of sufficient concern to not make a tenure appointment?’”

The ad hoc is the mostly anonymous end to Harvard’s tenure process—when the dozens of classes and published papers boil down to a single decision. Many tenured and tenure-track professors say the process is unfair, that it is too subjective, too anonymous, and too unpredictable. But fairness may be beside the point. Those familiar with the process say Harvard is not interested in promoting good junior faculty, but rather in making sure it has the very best.

Quite a few very successful chemists were formerly assistant professors of chemistry at Harvard (who left for a variety of reasons). Steve Benner is one of my favorites.

2) Earlier this month, Slate published an essay by a humanities graduate student about how going to grad school was a huge mistake for her.

Don’t do it. Just don’t. I deeply regret going to graduate school, but not, Ron Rosenbaum, because my doctorate ruined books and made me obnoxious. (Granted, maybe it did: My dissertation involved subjecting the work of Franz Kafka to first-order logic.) No, I now realize graduate school was a terrible idea because the full-time, tenure-track literature professorship is extinct. After four years of trying, I’ve finally gotten it through my thick head that I will not get a job—and if you go to graduate school, neither will you.

I know the situation is different for students in the sciences, but I think some of her experience is still applicable. Here’s a more charitable assessment of going to graduate school in the sciences from last year, also in Slate.

3) Finally, an oldie but goodie from 1999: “Don’t Become a Scientist!”

Why am I (a tenured professor of physics) trying to discourage you from following a career path which was successful for me? Because times have changed (I received my Ph.D. in 1973, and tenure in 1976). American science no longer offers a reasonable career path. If you go to graduate school in science it is in the expectation of spending your working life doing scientific research, using your ingenuity and curiosity to solve important and interesting problems. You will almost certainly be disappointed, probably when it is too late to choose another career.

While I like Professor Katz’s piece, it should be noted that the man certainly has some strange opinions.

I have a confession. I know I am not supposed to admit it, but I love teaching. Don’t get me wrong—I love research too—but there is something about passing knowledge to successive generations that is so purely constructive that I don’t see how you could do anything but enjoy it.

Aside from the satisfaction of helping students learn, teaching has also given me the chance to continue thinking about the foundational material of chemistry that made me fall in love with the subject in the first place. And one irony in teaching others is that you regularly find that you are the one who learns the most. Teaching is excellent at identifying even the smallest gaps in your knowledge, as students are quite proficient at exposing inconsistencies in the material presented to them.

A recent column in Nature Chemistry brought my attention to Berate My Professor, a blog written by an anonymous professor of chemistry. Inspired by the thoughtful and humorous tidbits that the mystery professor extracts from his teaching evaluations, I decided to go back and have a look through mine.

When you’re teaching, you get used to being the person responsible for handing out grades, so the close of each semester brings an element of surprise when the tables are turned and you must face the judgment of your students. Many instructors bemoan student evaluations as flawed, but I look forward to them. As regular readers will note, I value all forms of feedback and comments. Perhaps there is a skewed element to the process in that teacher evaluations are made public while student grades are not, but I have no problem with that aspect of the system. Teachers, in theory, are more mature and should be able to handle public criticism. Furthermore, students (and their parents) are paying for a service and deserve to collect information to guide their decisions. While disgruntled students may use the anonymous forum to exact revenge on teachers they dislike for personal reasons, I have to believe that these cases constitute the minority. Having participated on both ends of the evaluation process, I think that the majority of students provide thoughtful praise and criticism. That’s not to say that the feedback is always polite, but it is usually honest.

Below, for your enjoyment, I have posted a scanned copy of every single student evaluation I have received from the courses I’ve taught. These records are complete; I have not omitted any negative evaluations or censored any negative comments. But to respect the privacy of my colleagues, in instances where other teachers were evaluated on the same page as me, I have redacted their names using black rectangles.

My first gig as the leader of a recitation section at Harvard was for Chem 27, the “Organic Chemistry of Life” (see evaluations). I played soccer for six years as a goalkeeper, and looking back on the experience, I cannot remember any of the saves that I made. Not one. But I can remember most of the goals I let in, and my most vivid memory of my athletic career is of our team losing the final of an all-star tournament on penalty kicks. A similar bias in my recollection holds true for my teaching evaluations. Despite the fact that I had a good set of evals and won a teaching award from the College for my work in Chem 27, the only comment I can remember is this one:

Bracher was quite good. At times, however, he did not adequately understand the subject material.

Grrrrrr. After viewing this comment for the first time, I tried to figure out if it referred to a specific lesson, but I came up with nothing. In hindsight, it should not have come as a surprise. This was the first course I’d ever taught and my section was filled with a bunch of hard-charging premedical students at the greatest university on the planet. That said, there can be no excuses. I just wish the comment were a little more specific.

My wish for specificity is one-sided, because I have no problems accepting general comments like “Paul is the man.” This first set of evaluations did a lot to impress upon me that students really appreciate humor, good review handouts, and hard practice problems (with solutions). Seeing comments like the following really made my day:

Paul was amazing – dedicated, enthusiastic, and extremely helpful. Fabulous handouts, extra office hours – I won the TF lottery!

The next semester, I packed up the lessons I’d learned from Chem 27 and stepped up to the plate in Chem 30, the second semester of organic chemistry for majors at Harvard . It was a great experience, and I thoroughly enjoyed it. Come evaluation time, for an instant, I knew what Don Larsen must have felt like in the ’56 Series, the excitement that coursed through Mary Lou Retton after her vault in the 1984 games, and the elation experienced by the ’72 Dolphins. I had a perfect semester: 5/5 responses from every single student on every single evaluation criterion (see evaluations).

I know people on the Internet only want to see my negative and insulting evaluations, so I’ll just move on. Sorry, there were none.

I had the opportunity to teach Chem 30 again the next year with a new (world famous) professor. Again, it was a great experience. For the first time, instead of having to start my handouts from scratch, I had the opportunity to focus my effort on making quality revisions and taking the handouts to the next level. I think the students appreciated the effort too, especially since some of them felt frustrated at the challenging problems presented by the professor that year. I am all for hard problems, but you quickly learn that if you’re going to assign hard problems, you’re going to have to spend a lot of time in office hours or review sessions if you want to avoid a student revolt. My student evaluations did not rise to the level of perfection attained in Fall ’03, but I’ll stand by them any day (see evaluations).

I think the pinnacle of praise is when students who are not in your class start showing up in your class for fun. Of course, this can be especially rewarding when it’s time for evaluations:

I really didn’t have Paul as my section leader, but I attended his section because of time conflicts and because he’s so amazingly good. I really appreciated the time and effort he put into preparing for his section and that he tried to make it fun (he’s funny! =D)… Improve [section] by cloning Paul and making him the only section leader.

And that’s all I have for now. An eminent professor of chemistry at Columbia once taught me that you should maximize perceived productivity by publishing the same paper two or three times. Consequently, I’ve decided to cross-post this write up on my personal site. Please don’t turn me in to the Internet police.

There is nothing like a trip to my mailbox to bring a nice little blogging hiatus to a crashing halt. While attacking my pile of C&ENs, I caught this ad for TOSOH Organic Chemical Company on page 43 of the 11 June 2012 edition:

I guess the hair net and painter’s mask ensure that—unlike my Orange Chicken at Panda Express—these products arrive free of human hair. Matters of lab attire aside, what actually piqued my interest in the ad were the compounds for sale:

Sigh. That is not how I was taught to name organic compounds. My orgo professor—on the recommendation of IUPAC—told us to start by numbering the longest chain of carbons. Thus, 1-bromo-2-ethylbutane is properly named 3-(bromomethyl)pentane, and 1-bromo-2-ethylhexane should be 3-(bromomethyl)heptane.

Avid readers of ChemBark know that I love trick questions, and structures like the ones above make for great nomenclature practice. Many students will instinctively assume the carbon chain extending from left to right is the longest. When I taught orgo, I had to purchase red pens by the dozen.

One overlooked aspect of the importance of wearing safety glasses in lab is the protection they afford to UV light. A report in today’s Harvard Crimson reminds us of this fact:

On Tuesday afternoon, about 60 LPSA students headed to Science Center 117 to complete the last lab of the semester, which involved observing DNA samples placed on a transilluminator that emitted ultraviolet light.

Although a protective shield is supposed to cover the device whenever students make observations, some students did not use the shield correctly while viewing their samples. Some were also not wearing safety goggles, resulting in temporary injury to their eyes that caused irritation and blurry vision a number of hours later, according to students in the course.

A number of students were sent to the hospital, although no one is expected to suffer permanent damage. This incident should serve as yet another reminder that you can’t get lazy about personal-protective equipment in lab just because “oh, we’re not working with fire or chemicals, so it should be okay”. Also, while it sucks to have to be the bad guy, when you are a TF (or TA, in non-Hahvahd speak), you must continually pester students who fail to wear their safety gear.

While almost all laboratory safety glasses sold nowadays have a UV-protective coating, one easy way to tell if yours do is to use your set-up for running TLCs. When you put your glasses in between your UV lamp and a fluorescent TLC plate, the fluorescent green color should go away.

Photo credit: Mark E. Brady, PGFD

Earlier this week, something went wrong in the sophomore orgo lab (CHEM 242 class) at the University of Maryland, and two students were injured in an explosion+fire. The details (and pictures) were almost immediately posted to the PG County Fire Department’s Web site.

The fire department announced that the cause of the accident was the addition of a nitric/sulfuric acid mixture into an (organic?) waste container. Jyllian Kemsley^[1] of C&EN interviewed UMD chemistry department chairman Michael Doyle, who had a slightly different story. He believes the accident was the result of adding the nitric acid to a bottle with an organic reagent in it (not necessarily a waste container).

Mitch has raised this issue before, but it is worth repeating…If you are teaching orgo lab and your students are using nitric acid in high concentrations, you must Must MUST tell them to be careful that the HNO₃ does not come into contact with the acetone or other oxidizable solvents you’ve given them to wash their glassware. You had also better label the organic waste bottles that day with a warning that adding HNO₃ will cause the bottle to explode.

[1] Incidentally, I am a huge Jyllian Kemsley fan. C&EN‘s safety beat writer has done a phenomenal job covering safety issues in academic research, including the tragic case of Sheri Sangji at UCLA and the jaw-dropping idiocy of Preston Brown at Texas Tech. Kemsley runs a blog, the Safety Zone, on C&EN‘s Web site. It is the place to go for news pertinent to chemical safety.