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Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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January 29, 2006

Name Reactions for One Thousand, Alex

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Posted by Derek

Here's a question for people who have been out interviewing in the last couple of years (with special emphasis on those who've been seeking their first position in the industry): does anyone still do the old "Let's go to the blackboard and see how many reactions you know" interview? Syntex in Palo Alto was well-known for putting people through this twenty years ago or so.

I got a couple of those back when I was first looking around, and I'd be lying if I tried to tell you that I liked them. (I did OK under these conditions, but while you're up there on you're always worrying that the next question could be the one that makes you look like an idiot. The whole thing is too close to a PhD defense to be anything but unpleasant.

And I never understood the point of this technique to start with. Chemistry is not done solo in a spotlight in front of a hostile crowd. It's important to be able to speak coherently in front of people, of course, but that's what a seminar (and its associated questions) are for. It's also important to realize that a person who can whip out answers quickly might be an even better scientist if they trained themselves to slow down and think a bit.

Knowing the mechanism (under time pressure) for the Nosenko-Golitsin Rearrangment doesn't seem to be a good predictor of research success. That was true back in the late 1980s, when I was the guy at the blackboard, and I think it's even more true now. SciFinder and the other computer databases have really gutted the rationale for committing large numbers of transformations to memory. It's important to know what sorts of things can be done, but there's little point in memorizing exactly which reagents do them and what journal they appeared in. You can always look that up, and when you do you'll likely find a dozen alternatives that you didn't even know about.

These days, being able to sort out all those potential reactions into an order of plausibility is a more important skill than just memorizing them. I think I might work up some questions like that for the next time I interview someone. "Here," I'll say, handing over a sheet of paper. "SciFinder says that you can do this reaction any of these six ways. Which one would you recommend trying first, and why?"

Comments (19) + TrackBacks (0) | Category: How To Get a Pharma Job


1. Brian on January 29, 2006 10:12 PM writes...

Heck, I just had my Ph.D. defense, and didn't get anything even remotely resembling a name reaction question. Have these questions gone out of style everywhere, or just my department?

As a first time industry interviewee, most of the chemistry questions I had were 'how would you go about making this molecule?' I thought those were pretty fair.

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2. Lars on January 30, 2006 2:51 AM writes...

I have been to a few/organized a few interviews in the past 2-3 years and I also see a trend moving away from classical name-reactions and arrow-pushing towards assessing the breadth and general desicion-making ability of the candidate.

I think a working knowledge of areas outside specifically chemistry (eg. ADME, tox, drug-metabolism and other preclinical profiling parameters) will be more useful to medchemists in the pharma industry in the future.

Come to think of it...the last time I had a name-reaction question was in 2000 when I interviewed for my postdoc at Roche Bioscience...formerly Syntex-Palo Alto...go figure.

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3. Tom McEntee on January 30, 2006 7:16 AM writes...

Nosenko-Golitin Rearrangement...let's see...ahh yes...this is the flip-flopping of the stories of two Soviet defectors back in the 1960s, each of whom offered up the other as the double-agent during their debriefings by US intelligence. Seriously, I spent 8 years working for Syntex at their Boulder process development and manaufacturing operation. This included many trips to Palo Alto for meetings, including the Consultants Meetings where nervous Syntex post-docs got to present their work to the likes of EJ Corey, Gilbert Stork, and others. The consultants certainly never subjected people to "Name That Reaction" and I never heard of the practice being applied to job applicants. But it was a competitive environment and I can close my eyes and see some applicant being asked "So, Dr. Nervoos, tell us what you know about the Nencki reaction"...

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4. Derek Lowe on January 30, 2006 8:47 AM writes...

I was wondering how long it would take someone to get my name-reaction joke! It sounds like a plausible one, though, doesn't it. . .

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5. RKN on January 30, 2006 9:09 AM writes...

Before beginning my present reinvention in the life sciences, about five years ago I went shopping for a new job in scientific software development. The market for that was hot then and I quickly arranged five or six interviews. One asked that I come prepared to give a mini seminar on a relevant project I had done, others gave me written tests, and one sat me down at a computer and said, "Code a solution to the following problem..." That one was particularly frustrating because the proctor admitted to me that there was no way I could complete the "test" in the thirty minutes allotted. They said I was welcome to finish the problem at home and e-mail them the solution. Homework! I did so, but they didn't offer me the position, the other companies did.

I'd prefer a less challenging interview, but I have to admit that when applying for a technical or scientific position, relevant tests and/or problem solving questions are entirely legitimate. My thought is that good interviewers are less concerned with you getting the right answer, and more interested in how quickly you can break down a problem and suggest multiple hypotheses for solving it.

A common question given to people applying to Microsoft for a position as a programmer used to be, "Suppose I give you a 20-digit integer; programmatically, how would you go about determining if the number was prime?"

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6. tom bartlett on January 30, 2006 9:44 AM writes...

I agree about name reactions, but, frustratingly, I find on interviews I get mostly touchy-feely HR-inspired questions instead of technical questions. It bugs the hell out of me. Maybe they figure that's a good way to "stress interview" a scientist.

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7. Demosthenes by day on January 30, 2006 9:57 AM writes...

My favorite interview horror story comes from Ciba in 1984 when one of my interviewers gave me a pop quiz. He handed me a sheet of paper with 10 chemistry questions on them and asked me to take it. He also told me time was a factor. I finished in 5-10 minutes and got them all right. But I sat there infuriated. I was on my first cycle of interviews, and this happened halfway through, and while I thought I had done enough in other interviews to get a job offer I didn't have one yet so I grinned and smiled and said yes sir. Anyway it made it easy to turn down Ciba's offer when it came. Although it was a recurrent daydream to go back and interview again but this time take the pop quiz fold it up into a paper airplane and boink it off the interviewer's nose.
I've always found the most effective interview technique is to ask the candidate about their own research. I've always goten a truer sense of how a scientist thinks when they talk about how they dealt with their own research trials and tribulations. The idea of putting someone through pop quizzes whether in paper or whiteboard form just seems lazy on the part of the interviewer, to me.

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8. LNT on January 30, 2006 10:01 AM writes...

I'm happy to say that I've never had a "name reaction" quiz on an interview. (I've been on 7 or 8 over the past 4 years) The closest experience I've had was at a synthesis CRO. The VP (a chemist) drew several molecules on a whiteboard and asked me how I would go about making them.
I'm also happy to say that I haven't had too many of those "HR" quezy questions (except from the HR representative that they always schedule you to meet with). Most of the interview conversation centers around the seminar and around topics on my CV.

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9. Chemgrad on January 30, 2006 12:27 PM writes...

I guess that is a waste of time and energy. I am familiar with these questions.Faced a similar type of question in my qualifiers a couple of years ago.
I don't understand as to why that is important.As Derek, U point out...remembering name rxns, all of them to memory is not a test of how good a scientist u are.

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10. PDOC on January 30, 2006 2:13 PM writes...

From my experience interviewing so far this year, I would say the quizzer questions are rare, process interviews are an exception, though. One person seemed quite dissapointed that I did not suggest Nitrogen NMR as a means to probe a certain reaction mechanism. I have used a lot of NMR techniques in my synthesis work (the typical hydrogen and carbon stuff, boron, phosphorous, fluorine) I never even heard of using nitrogen NMR!

I get a lot of HR-type questions, from chemists as much as from HR. Give me an example of a team you worked on? How have you resolved a conflict that has arisen? What happens when you and your advisor dissagree? blah, blah, blah.

As an aside, the job market is awful this year. I am doing a pdoc at a top instution working for a renowned chemist. I have had several site interviews but no offers. There are very few jobs out there. Have I been slaving away for the past 2 years only to have to beg for one offer?

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11. SRC on January 30, 2006 2:29 PM writes...

SciFinder and the other computer databases have really gutted the rationale for committing large numbers of transformations to memory. It's important to know what sorts of things can be done, but there's little point in memorizing exactly which reagents do them and what journal they appeared in.

About ten years ago I was on a board evaluating a chemistry department some years ago when I commented to the organic faculty that we were probably the last generation who would know (or need to know) the name reactions in detail because computers would shortly render that knowledge irrelevant.

Fortunately, the tar took some time to liquify, and they didn't have feathers to hand, which allowed me to beat a hasty retreat. That comment definitely hit a nerve, but its truth was foreseeable then, and is certainly manifest now.

Good thing I didn't mention that in time programs for retrosynthetic analysis will probably obviate that skill as well.

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12. Still Scared of Dinosaurs on January 30, 2006 2:35 PM writes...

Slightly off topic, but the worst interview nightmare I ever heard of was for Pharma sales. The candidate pool for a given position would be whittled down to three candidates who would all be invited to a final interview at the same time, Dating-Game style.
I've never had someone do something that felt like playing a game in an interview. I strongly feel that the management of employees is at its worst when in amounts to an inflexible "This is your job title and this is the description so go do it. Don't ask for help." Some folks are better at keeping the wheels rolling, some are better at fixing the broken ones, and some are better at figuring out why the broken ones broke.
I feel that interview techniques that try too hard to put candidates on the spot or see how they perform under pressure are used by people who are going to manage employees in the same way.

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13. CMC_PM Guy on January 30, 2006 8:47 PM writes...

I always had a habit of looking up and reading the papers of the staff that was scheduled to interview me. Did it even when I interviewed for a Director's position a couple of years ago. It came in handy when the VP pulled out his latest paper and asked me to draw a reasonable mechanism.

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14. Lucas on January 30, 2006 9:34 PM writes...

I recently interviewed for my first position in medchem, and I faced something like what you describe, though not nearly as intense and at a fairly basic level. It was more along the lines of "do you know some basic transformations and how they occur?"

I was first asked how I'd separate a mixture of aniline, phenol, and benzoic acid - basically to get an idea whether or not I know how to separate things and when it's better to use chromatography, extraction, distillation, etc. Then they gave me a couple of simple transformations based on that - N-alkylation of the aniline and conversion of benzoic acid to an ester. They gave me an unsymmetrical ketone and asked how to alkylate at either alpha carbon, then a fairly simple retrosynthetic analysis. Nothing complicated on the last - more like "where would you break this up to get it into easily manageable chunks?"

All in all, I felt like it was a good test - it didn't get into stupid details I would just look up on SciFinder, but established that I know the basics of how organic molecules react and know how to attack a problem.

Interestingly, they said that the retrosynthetic analysis question is one they usually ask Masters candidates, and many people have trouble or simply can't find an answer. I know that this is a skill that's becoming less essential as databases become more extensive and reaction searching software becomes more robust, but it still seems like understanding what bonds are easy to form (and what bonds aren't) is a key part of knowing how to build molecules, and something students should learn. Am I just behind the times, or what?

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15. Dr Snowboard on January 31, 2006 4:34 AM writes...

In answer to Lucas,
No you're not behind the times. Retrosynthesis shows you know your subject backwards (pun intended) and often more important, laterally.

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16. LNT on February 1, 2006 9:33 AM writes...

SRC wrote:
About ten years ago I was on a board evaluating a chemistry department some years ago when I commented to the organic faculty that we were probably the last generation who would know (or need to know) the name reactions in detail because computers would shortly render that knowledge irrelevant.
Good thing I didn't mention that in time programs for retrosynthetic analysis will probably obviate that skill as well.
That's an interesting observation. I wonder what synthetic chemistry will "look like" in another 10-15 years. Prior to ever going in the lab, will we submitt structures to a computer program that will "analize" the structure for the most efficient method of synthesis? Interesting... My number one wish for the future: a preparative HPLC/MS/NMR. You submit a crude sample in DMF/DMSO and the machine purifies it and characterizes it at the same time. Interestingly, I don't think that technology is too far out there...

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17. milo on February 1, 2006 4:50 PM writes...


Check out this cool lab toy:

I am not sure if it is prep scale or not, but it sure is nifty.

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18. Leblbdor on June 25, 2008 12:10 PM writes...

Of course, but what do you think about that?,

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19. Leblbdor on June 25, 2008 12:12 PM writes...

Of course, but what do you think about that?,

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