Orgo Thursdays

ed_academic_bigOne of the nice things about being a professor is that you have the agency necessary to successfully garner support for causes you feel are worthwhile. Earlier this year, I brought to SLU something that I had sorely missed from my time as an undergrad at NYU: organic division problem sessions. These were held once a month during the school year and worked as follows:

Each organic group took turns hosting the sessions. The hosts would be responsible for bringing pizza, beer, and 3 or 4 hard, graduate-level organic problems. The organic students and faculty would gather at 6 pm, eat, drink, and work the problems. Volunteers would put up their answers, the audience would nitpick and argue, the faculty would weigh in with suggestions, and if no one could figure them out, the people who brought the problems would set us straight.

The attendance of organic graduate students was expected, and undergraduates were welcome to attend. In something of a paradoxical twist, I think these sessions were instrumental in both (i) making me appreciate that organic chemistry is hard and (ii) making me feel like organic chemistry was something I could do.

At Harvard, I attended Christina White’s monthly organometallic sessions, even though I was the dumbest participant by far. Each person was responsible for bringing one slide that summarized a recent paper from the literature. While these weren’t problems, there was a fair amount of arguing over mechanisms. The White Lab’s departure to Illinois marked the end of these sessions for me. It’s kind of unfortunate that Harvard had nothing else—that I know of—considering the rich history of late-night organic chemistry seminars at Harvard led by Woodward.

Earlier this year, I decided to champion these blasts from the past and start one at SLU.

On the third Thursday of every month, I host a voluntary organic problem session. I bring pizza and three graduate-level problems, and the students work them over, present ideas, and face my ridicule—or occasionally, approbation. Usually I steal problems from texts, but if I’m feeling saucy, I’ll write them based on interesting papers I’ve come across and stashed away.

While attendance at Orgo Thursdays is completely voluntary—except for my grad students, for whom the session replaces group meeting that week—we’ve averaged 12 participants over the first seven sessions. That’s makes the sessions just a shade smaller than those at NYU, and isn’t too shabby given the size of our department.

Now that I’ve seen these sessions from both sides of the table, I am convinced of their value in a number of areas:

1. For any skill, if you don’t use it, you lose it. The problems keep students and me thinking about fundamental course material long after final grades are in the books. The continued practice is going to help our grad students become better teachers and perform better on their comprehensive exams, which are taken in the summer between their second and third year.

2. There is something to be said for placing students in uncomfortable situations where they have to think on their feet and be brave. This is a life skill that classes often don’t focus on developing.

3. These sessions are a great opportunity for everyone to interact with people from other research groups. I believe strongly that departments should actively foster wide collegiality, where students and faculty have meaningful interactions not only with their labmates, but with people in other labs. Such an environment is so much more enjoyable and supportive than when each group is an island.

4. These sessions help me get to know our students better. It’s never a good situation when a professor has to write a ‘third’ rec-letter for a student he hasn’t talked to since a class four years ago.

5. The problem sessions give undergrad students an opportunity to stay involved in organic chemistry after their sophomore classes in the subject are done. Undergrads also get a taste for what graduate school is like, given they are working graduate-level problems alongside our graduate students. When I was an undergrad, it was empowering to participate in these sessions.

My plan is to keep hosting Orgo Thursdays until I run out of problems or money to buy pizza. So long as people keep coming, I assume they see value in the activity too.

Papers That Got Off to a Good Start

This week, an interesting discussion on Twitter was sparked by the publication of this paper in JACS:



That’s a great first sentence to a paper, and soon people chimed in with other memorable examples.


Tehshik Yoon pointed out this review on C-H activation as his favorite:



…which Nicolas Fanget countered with a microbiology paper from 2000 that begins with a quote from Monty Python’s Flying Circus:



My personal favorite belongs to the man himself, R.B. Woodward, who began a 1963 paper with the simple exclamation, “Strychnine!”:



Are there any other chemistry papers out there with memorable openings?

Textbooks Make Me Feel Dirty

ChemBark Ed on Dollar BillWe’re three weeks away from the start of the semester at SLU, and this time of year always brings the first wave of e-mails from the next class of students. While these messages vary in length and tone, they can generally be distilled to one question: “Professor, what do I really need to buy for your course?”

Can I use the previous edition of the text? Do I really need a model kit? Do I really need the model kit on sale in the bookstore? Can I share my model kit with a friend? Do I have to buy the subscription for the online homework?

Whenever I read these e-mails, a part of me dies inside. I feel their pain. They’ve just paid their bills for thousands of dollars in tuition, with two more years of it to go. And now, after absorbing that massive hit, they’ve got to scrounge up another $375 dollars for my coursepack. It’s a slap in the face.

The cost of these materials makes me sick, and the prices are rising at an astounding rate. For my college organic text, I paid less than half of what students are asked to pay today. Are today’s books really worth double my book, which remains a valued reference on my office bookcase? Has our understanding of introductory organic chemistry really changed that significantly in the last 15 years? No.

I’ll be teaching Organic Chemistry I for Majors again and using the same coursepack we did when I arrived at SLU.¬† It contains: (i) the textbook, (ii) the solutions manual, (iii) a plastic model kit, and (iv) a subscription to the online homework assignments. That all costs about $375 when purchased together.

Three hundred and seventy-five American dollars!

While I could easily point the finger at the publishing companies as the villains that they are, ultimately, they are not the problem—I am. After all, I’m the one who assigns the books for my course. And for that, I’m truly sorry, but allow me to explain:

While there are a dozen good organic texts, I think we can all agree that it makes sense for a class to adopt a single textbook. As a teacher, I literally want everyone on the same page, with a precise understanding of what information everyone is responsible for. In the absence of a strong external force, inertia will govern this decision. It makes sense for an instructor or department to stick with the book it used the previous year, because the switching costs of an instructor having to rework the syllabus, slides, and order of practice problems can introduce a lot of unnecessary work. And there are benefits to students when we use the same book as the year before, because they can buy a used version. Furthermore, they can get something out of borrowing their friends’ old notes and exams.

Now, here’s where the publishing industry appears and sinks in its fangs. The used-book market poses a serious threat to their revenue stream, because they only make money by selling new copies. It’s the bookstores and old students who make money from the used-book market. So, what do the publishers do? Release a new edition! By releasing a new edition, the publishers can (i) find professors to drive orders of new books and (ii) stop printing the old edition so colleges can’t find enough used copies of it, forcing adoption of the new edition.

These new editions usually contain few or no substantive changes relative to the previous edition. It can be as silly as shuffling content between chapters, renumbering the practice problems, and adding a few new photos. Case in point is the 4th edition of the text I use now. Anyone with the 3rd edition would have no problem following my class, because hardly anything changed.

Another thing that burns me up is that by the 4th edition of a text, you’d expect all of the errors would have been ferreted out and corrected by now. Have they? No. I maintain a list of errata in the text on my webpage and use it to show my students that organic chemistry must be hard—not even the textbook’s author can get it right.

Textbook publishers erode the used-book market to drive the sale of expensive new editions, but professors are complicit in maintaining this skewed market. Why? Because we are the ones that assign these textbooks as required course materials. And you know why professors don’t especially care? Because we get our textbooks for free. The publishers will just give away a $250 text to us because they want us to force 200 students to buy it. They’ll even sweeten the deal by giving us free lecture slides that correspond to the text. The sales technique is brilliant: make life as easy as possible for the professors and give them free stuff so that they will force their students to buy your product. While it’s not exactly a kickback, it’s not terribly far from it.

So, the textbook market is not a fair one as far as students are concerned. Students can’t shop around for the highest quality book at the best price; they are essentially required to buy whatever textbook their professor decides at whatever price the publisher is charging. And as if that wasn’t enough to make you sick, publishers send instructors e-mails like the one I received a month ago:

From: <Textbook Publisher>
Subject: When it’s required, they’re prepared required_advert_450Disgustingly shameless. I feel gross just reading it.

Hey, instructor buddy! You want your students to learn? Well, then you need to *require* them to purchase our expensive online add-on! And don’t worry—we’ll give instructors free access to the system, of course!

Don’t get me wrong. I recognize that authors and publishers perform a valuable service. While our understanding of first-year organic chemistry hasn’t changed in 30 years, our ability to make instructive figures has certainly improved to the point that no one would choose a text from the 1980s over those offered today. So yeah, publishers should be compensated for the materials they produce. But at the same time, there is a limit to what is reasonable. Issuing a ‘new’ edition every three years at $375 a pop is ridiculous.

So, students, please forgive me. I know the system is unfair, but there really isn’t a good alternative at the moment. I would much rather you spend $375 on a nice iPad and download the coursepack for free. Unfortunately, the free organic texts in existence pale in comparison to the expensive texts out there, and the time required for a professor to produce all of the necessary materials for a class is too much to do in one shot. I hope you will believe me when I say that I’m working on it, but it’s going to take some time. Every year I produce a little more material and build towards the goal of obviating the need for an expensive text. Give me 20 years and that should become reality. I hope someone else beats me to it.

C&EN is Cutting Staff

CEN Fake Cover of Paul BracherYesterday brought the alarming report that Chemical & Engineering News (C&EN) is cutting eight members of its staff. It appears that these cuts are rooted in the continued sag in advertisements and other sources of revenue at the magazine.

If I recall correctly, C&EN had a similar cutback when the economy tanked, and it is alarming to see a new round of cuts. I think C&EN serves an important and underappreciated role as the major—sometimes, only—means by which many ACS members keep track of chemical news, major advances, and society business. For any large democratic organization to operate efficiently, good journalism is required to keep the electorate informed.

Based on grumbling in comment threads, I think many people are skeptical whether C&EN fulfills this role, but the magazine is really the only publication that comes close (as far as the ACS is concerned). It is more than distressing to see these cuts and think what they mean for the coverage the magazine will be able to provide. Will there still be resources to send reporters to courtrooms (as with the Patrick Harran case)? Will the magazine pursue misconduct cases with the same vigor it has in the recent past?

I know that C&EN recently underwent major changes in its editorial staff, and I hope that means they will be reevaluating their approach to ‘new media’. There is revenue there, along with the chance to engage a wider audience. Given the latest round of cuts, it’s obvious that staying the course and relying on a traditional model is not working. When one looks at the direction of major news outlets like the New York Times and Washington Post, it is bizarre to see that C&EN shuttered its CENtral Science blog network. The blog platform never got the resources it deserved. There was never a full-time blogger who could throw herself into the system and innovate, rather than juggling a responsibility to pump out stories for the print edition.

I’ve got to wonder whether anyone there ever considered the obvious move of hiring Derek Lowe, the godfather of the chemical blogosphere. Given Lowe’s problems ‘under the hood’ at Corante and his impending move to Science Translational Medicine, I have to imagine C&EN could have made a competitive offer. His blog would have represented a strong foundation at C&EN on which to build.

But that ship has sailed. I hope the magazine’s future efforts experience fair winds, because the chemical community needs and deserves good journalism. Fortunately, the staff at the magazine is a great group of people. I hope the Society gives them the resources and editorial latitude they need and deserve to keep the membership well informed.

Chemistry Error on Seinfeld

Something didn’t quite look right when I saw this scene from ‘Seinfeld’ in real time:

Closer inspection of the fire diamond reveals the flammability rating of the paint thinner to be 8:


That’s pretty impressive, considering the maximum score is 4 on the NFPA 704 standard. If acetylene is a 4, I wouldn’t want to be driving around town with an 8 in my trunk.

For those curious, the episode is ‘The Pothole’ from Season 8. The IMDB page for the episode already lists the scene as a goof.

Longtime readers will remember that this is not the only time Jerry Seinfeld has used chemistry for laughs.