Orgo Thursdays

August 10th, 2015

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.

13 Responses to “Orgo Thursdays”

  1. paula kazarosian Says:

    Hello Paul,
    First I’ll let you know I am not a PhD scientist. I am a recruiter who has worked with scientists for many, many, many (ugh, I’m old) years.
    Your thoughts recalled a conversation I had with Ray Firestone, a wonderful old curmudgeon of a man who was at Merck for many of the early years, then BMS, then BI. He is now in his 90’s and still has an amazing website with lots of thoughts and questions ( put up for discussion.
    Anyway, during that conversation he had mentioned to me that the demise of Merck (in his opinion) started when they stopped having pizza and beer sessions for any and all chemists/scientists. They used to have these once a month and hundreds of people would show up and just talk about science and chemistry problems, not just happening at Merck but in other companies and institutes as well. He speculated that the pure love of science and the problems endemic to science drives the passion in a scientist to solve those problems. And I would argue that man ,being a social beast, does not typically function best in a vacuum. So the connection you are providing is of great value!!
    keep going, produce lots of great students and ENJOY!!

  2. Curious Bond Maker Says:


    Would you consider posting the problems from the sessions online after you’ve discussed them? It would benefit us as well, even though we are missing the actual insight from the sessions. Thanks.

  3. LiqC Says:

    These events were called colloquia in Russia, and where a graded part of many courses. They would usually be held 2-3 weeks before the final. You don’t get to take the final unless you pass the colloquium. Often they would last for multiple days, for up to 6 hours each, until all students would arrive (often in groups) at the answers to their problems and could explain (individually) them to the professors.

  4. Hap Says:

    1) One of the characters in a book I read said “What happened to weekly spelling bees? It’s the only activity I would have signed up for.” I felt that way about mechanism problems (though that explains grad school for me, I think.)

    2) One of the things that was missing at Harvard that would have helped was an introductory get-up-to-speed session. When I took grad classes in undergrad, the first three weeks of class spent roughly two hours a week on a list of mechanism problems. They went over some of the mechanisms for reactions people might not have seen for a while, in groups of about fifteen. This might have been helpful. They also had synthesis problems that were done in groups of four grad students among the synthetic groups; that would have been interesting, but less generally useful than mechanism problems would be. (It would also be hindered by the fact that in some cases, groups at Harvard aren’t playing nice and work on the same targets – I think two of the spongistatins were studied by the Kishi and Evans groups, for example.)

  5. Will Pearson Says:

    A wonderful post. Problem-solving sessions were one of the most important portals for learning (and teaching) that I experienced in my training and my time as a faculty member. I agree with your five areas of value and will add another:

    6. Learning how to give feedback and guidance in a way that encourages learning. When someone is up at the board and is stuck or has gone pretty far astray, what then? It’s tempting for an audience member to blurt out the answer and show their chops, but that may be a missed opportunity for learning. Many times, the person at the board has it in them but doesn’t know it or hasn’t yet found it. Skillful questions and nudging from the audience, offered in “teaching mode,” can help him or her find their way. Embarrassment turns to excitement and then to confidence. If everyone is encouraged to put on their teacher hats, it’s amazing what can happen.

    When someone is stuck or off track, It can be helpful as the facilitator to say to everyone, “Let’s pause for a moment here. How are we doing? Can anyone provide some guidance?” Next thing you know, rather than someone blurting out the answer, you hear thoughtful leading questions like “Where have seen something like this before? What is this like?” People get on board with helping this person make their own way through the problem. Naturally, those in the audience who are more senior and experienced have a lot to offer in this mode, so they still get to shine a bit. :-)

    I found this approach is a good one for getting new students up to speed and connected with the more experienced folks. The master of this was my PhD mentor Barry Trost. He almost never provided answers himself; he skillfully helped lay bare the way problems are solved. How does one tackle a problem one hasn’t seen before? What are the mechanics of problem solving? How can one help a less experienced person see that it’s not pulling a rabbit out of a hat? That one doesn’t have to be some sort of genius to do it? Barry was a genius at this. He could get the whole room pulling for the person at the board. As you can imagine, that has many positive repercussions.

  6. Poison Ivy League Says:

    While largely for “mechanism club” type meetings, I think that there is a real risk (especially for student and postdoc-generated problem sets) to try to “out-clever” your peers, above all else. The number of counterintuitive, obscure, and (ultimately) useless cascades that we did (I’m looking at you, Au-carbenes) seemed to be more to make everyone feel stupid than to refine/enrich mechanistic understanding…

  7. Hap Says:

    Unfortunately, I can see that happening (because I wanted to show how smart I was, though my projects and chemistry did not care one bit). I’m not sure how to avoid it – either people have to be relatively friendly (so that status isn’t all) or the moderator needs to be skilled. I don’t know if a mixture of undergrad and grad students would have helped diminish the “smarter-than-thou” impulses.

    When I was in grad school, it was the Pd-catalyzed cascade cyclizations.

  8. Paul Bracher Says:

    @paula: Very interesting to hear that these sorts of sessions used to be a big part of the culture at Merck.

    @Curious Bond Maker: I don’t plan on posting the problems from the monthly sessions because most of them I steal from books. What I do plan on doing in the near future is posting about my favorite books from which to steal problems!

    @Will Pearson: I completely agree with your statement:

    Many times, the person at the board has it in them but doesn’t know it or hasn’t yet found it. Skillful questions and nudging from the audience, offered in “teaching mode,” can help him or her find their way.

    I tend to go into coach mode when the first attempt doesn’t quite get there, giving progressively more telling hints. It’s better when other students post their ideas and we can ask ‘what should you be thinking here?’ and ‘how do we weigh these competing effects?’ In regular class office hours, I find that it is usually more valuable to have a student propose an answer and then analyze why the proposal is incorrect rather than for me to directly show a student how I would approach the problem.

  9. paula kazarosian Says:

    Thank Paul, for our response, I was surprised to hear it as well. I highly recommend your connect, either via his web site or by phone, with Ray. he is a unique and amazingly experienced scientist with so much to share and, well, frankly, not too many years left to do so.
    If you’re looking for tough questions to steal, check with him i bet he has a ton!

  10. Future Student Says:

    I found this by chance doing a bit of stalking on my future organic chemistry professor. You sound like an interesting guy, Dr. Bracher. Can’t wait to start the semester, although I am dreading your course I will say. Count me in for Orgo Thursdays.

  11. Paul Bracher Says:

    @Future Student: There’s a rumor going around campus that I’m pretty awesome.

  12. Hap Says:

    On one of the posts on In The Pipeline, Prof. Dan Singleton talked about his group’s activity, “What’s Wrong With This Paper?”. I think that might be less helpful for undergrads, particularly since I hadn’t started reading journals yet, but it might still be interesting for them.

  13. Phillip Says:

    My PhD lab’s group meetings always included a problem set, circulated before the meeting and discussed at the meeting. Each student worked up a problem set in turn (questions and answers). Sometimes they would be on interpreting spectra, sometimes on mechanisms etc. A favourite source of mine was Alexander McKillop’s Advanced problems in organic reaction mechanisms which presents transformations from papers, but doesn’t include the solutions (and some are seriously tough) – you have to work them out yourself, sometimes by referring back to the papers (if you can find them – you need to do a structure-based search usually, as the referencing is limited, which would be my only criticism of the book). Occasionally there’s a problem in there that comes from an unexpected reaction in a complex synthesis, which even the original researchers aren’t 100% confident on the mechanism, which always makes for an interesting discussion!

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