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DBL%20Hendrix%20small.png College chemistry, 1983

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: derekb.lowe@gmail.com Twitter: Dereklowe

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In the Pipeline

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March 27, 2005

Ten Questions

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Posted by Derek

1. Did the American Chemical Society realize, when it started the journal Organic Letters, that all it would manage to do is turn the competing Tetrahedron Letters into a European journal and force libraries to subscribe to both of them?

2. Can there be a more worrisome lab nickname than the one given to one of my wife's former co-workers, a radioisotope user known as "Mister Chernobyl"?

3. What percent of chemists are the same type as me: willing and able to start new reactions all day, just so long as I don't have to work them up and purify the products?

4. Are there still undergraduate organic chemistry courses that do a lot of the old qualitative tests in their lab sections - Tollens reagent and all that? (I deeply hope that no one answers "yes" to this one.)

5. When you're scheduled to speak with a visitor from academia, is there any more surefire conversation starter than "How's the funding going?"

6. Have I really been looking at the same gel in all those molecular biology lab presentations over the years, or does it just seem that way?

7. Will I ever have cause to use a spinning-band distillation column again in my lifetime? (Bonus question: at what point will I be the only person in my workplace to have ever seen one of the things?)

8. Did anyone ever actually use those crazy bar-code things, condensed versions of the tables of contents, that the Pergamon journals used to have on their first pages? (This is equivalent to wondering if anyone's ever made the "Mock Apple Pie" recipe on the Ritz cracker box.)

9. Is there any reagent more pyromaniacal than dimethyl zinc? (The stuff makes most of the other flame-spouting reagents look like chicken broth.)

10. Could there be anything less likely to attract members of the opposite sex than reading the Journal of Organic Chemistry while you're at the laundromat? (Yes, I did this in graduate school, and I can attest to its powers.)

Comments (13) + TrackBacks (0) | Category: Life in the Drug Labs


COMMENTS

1. Aaron on March 27, 2005 9:54 PM writes...

Re: Tollens test, etc. I took undergrad organic a few years ago (this would have been 2001? 2002? In that range) and yes, all the qualitative tests are still part of the unknown lab. Tollens test, iodoform, discoloring bromine in water, you name it. We did them all, then just used the damn NMR to figure out what we had.

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2. Greg Hlatky on March 28, 2005 6:05 AM writes...

No. 3: Me, me, me!
No. 9: Trimethylaluminum
No. 10: Try Inorganic Chemistry

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3. Derek Lowe on March 28, 2005 9:09 AM writes...

I've heard trimethylaluminum spoken of with admiration, but I've never used the pure material (just a 2M solution, which doesn't give you the full flavor.) Perhaps we can arrange some sort of flame-off. I note, though, that Aldrich will sell you straight trimethylaluminum, but they don't sell neat dimethyl zinc. . .

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4. The Novice Chemist on March 28, 2005 9:47 AM writes...

1. Yeah, but at least with Org. Lett. you get spectra and procedures. It's at least a glimmer of hope.
3. Count me in.
4. Yes, I did one in 1997.


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5. Drew on March 28, 2005 12:57 PM writes...


In reference to #1, did they also realize they would be making JOC more and more of a dumping ground journal, alighned with Tetrehedron itself?

Re#4, we had an Israeli post-doc (2000) who loved quan/qual spot tests, there is a huge bible of 'em, circa 1965 or so. Fast, easy, but in the era of LC/MS and GS/MS, why?

Re #9, I second the trimethylaluminum, yikes. BBr3 (neat) is pretty damn mean, too.

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6. Cameron on March 28, 2005 10:18 PM writes...

1. Seconding Novice on the procedures; if I'm SciFindering a prep and TL comes up, why bother? 3. Yep yep. 7. We have a spinning silica purification thing in the lab, but I'd never heard of a version for liquids before! 9. Triethylborane (neat) is good too.

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7. Derek Lowe on March 29, 2005 8:45 AM writes...

You have a Chromatotron? I used to use one of those myself; I'm glad that they're still around. A spinning band distillation column is a different beast, though - see www.brinstrument.com/fractional-distillation/spinning_band_distillation.html for an example.

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8. Jim Hu on March 29, 2005 2:28 PM writes...

#2. One of our first year students was given the nickname "The Berserker" by the other students. He cracked up during the first lab rotation.

#10 Discussing the relative merits of different ways to sacrifice lab animals? Friends of mine were doing this at a pizza joint and the people at the next table got up and moved further away.

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9. larry on March 29, 2005 3:26 PM writes...

#7: When I was in grad school, I lived at the spinning band column, purifying small ring hydrocarbons. I spent so much time there (as well as the prep gc, another story altogether), I contemplated getting my mail forwarded to the lab. #9: We were using Boron tribromide and then in a separate step adding in trimethyl aluminum. After some manipulation, we had to pull a vacuum, and we saw a green flame shooting out of the vent of the vacuum pump. We figured out it was trimethylborane bypassing all the traps we had set up.

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10. qetzal on March 29, 2005 4:51 PM writes...

#6. Speaking as one who got my Ph.D. in molbio, yes. It's all the same gel, originally run by Fred M. C. Seakem, a struggling grad student from Berkeley. The rest of us just use his photo.

Fred never did complete his Ph.D. Instead, he lives quite handsomely off the gel royalties. (He supposedly bought a small island using just the income from the CSI and Law & Order franchises.)

;-)

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11. Cameron on March 30, 2005 11:49 PM writes...

We had a post-doc who used the Chromatotron all the time my first summer in the lab, but I think it's been sitting in a corner for the four years since. Everybody's doing prep TLC these days, though I don't understand why ...

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12. Conservative Mutant on March 31, 2005 1:22 AM writes...

#4 Oh, yes indeed. ~2000. I particularly remember one (for amines?) that involved heating the unknown with a small lump of sodium in a test tube. Over a Bunsen burner. Why we never took a casualty from that is beyond me.

#6 Yeah. We run plenty of gels, but the bands always disappear when you transfer them to transparency, so it's back to the One True Gel.

#9 Happily, I've never had to work with anything more exciting than t-BuLi. But the borane commenters might get a rise out of "The Green Flame," the autobiography of one of the chemical engineers involved in the 1950s efforts to produce decaborane for "zip fuel" experiments. One (minor!) incident was the ignition of a dump full of borane-contaminated ether drums, which at intervals rose into the air and hovered on a column of green flame before exploding...

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13. NoFreeLunchMD on April 4, 2005 2:15 PM writes...

#4: As of 1998, youbetcha. Stanford University, chem...what was it, 136? Organic identification lab. Of course, it was kind of fun because most of the reactions we did were for identification purposes (tollens, and other things that pop, smoke, and change color). Of course, you had to determine a molecular weight (by titration), get the IR spectrum, the melting/boiling point, and have performed at least 3 tests for functional groups (tollens, bromine, etc) before they'd give you the NMR spectrum...which might or might not be a crappy-quality spectrum obtained before you were born (1977). The alarming thing about this lab was that that some of the chemicals they gave us were TOXIC, CAUSTIC, MUTAGENIC, CARCINOGENIC, and TERATOGENIC and they wouldn't tell us what they were!

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