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Inspirational Reads

Six Word Saturday, the Second Coming

March 28, 2009

Okay, so I had some fun the last time I did this. But then, the last time I did this, I was talking about pie and blow jobs. How can you not have fun with that???

Anyway, today's six words:

I should have been a cowboy!

Back when I was in graduate school at Notre Dame, the very first reaction sequence I tried could be summed up in the words "epic fail". Nothing went right with the material I had made, and it was a simple reaction of adding a Grignard to an epoxide in the presence of a Lewis acid. Simple stuff, right (trust me, non-chemists, a monkey could do this shit).

Problem never went.

I changed solvents (from anhydrous THF to THF from a still to THF run through our purification system); I changed the source of the Lewis acid (used three different bottles of copper(I) iodide from three different groups on the floor); I even remade the epoxide, thinking a different batch would help. Nothing. Still no product.

Now, for you non-chemists out there, a Grignard reagent is a kind of highly-reactive organometallic reagent, which means it mixes organics (carbon and such) with metals (bright and shiny and malleable) to give you something that will react wicked fast if you look at it cross-ways. That being said, you get a little water in there, and it all goes to hell. Fast. And being that northern Indiana in the summer is a bit...what's the word...*snaps fingers*...right, humid! A little bit of moist air and the bottle of vinyl Grignard you've got suddenly becomes magnesium-based sludge.

I suggested as much to my graduate school advisor. I know. The audacity of a first-year grad student saying "Maybe this highly reactive and water-sensitive reagent over here is the problem." My advisor insisted I was full of beans--or shit, take your pick--and gave me some different conditions to try, all using the same bottle of vinyl Grignard, all the while reminding me that what I was trying to do was a "literature reaction" (which, essentially, means that someone else has already figured this out, all I had to do was follow the recipe like a good monkey). Finally, after one of the last conditions still failed to yield the desired product, I closed my eyes, rested my head against the cool hood sash and said to myself (because everyone else in the lab was down at Happy Hour) "I should have been a cowboy..."

Yes, it was about that time that the Toby Keith song was popular, and if you've ever spent any amount of time in Northern Indiana, you'll know that country music is the aural poison of choice. Plus, I kind of liked Toby's sweet mullet.

To cap that off, I skipped work the next day (it was Saturday) and moved my stuff from my old, crappy apartment into the house I was sharing with three other guys. After moving, I was too tired to go to work, and--honestly--too pissed off with chemistry to worry about it. Unbeknownst to me, my advisor was in, running that exact reaction.

I came in Monday morning to find him standing near my hood. Figuring I was fired, he simply stated, "That bottle of Grignard is bad. Order new." And left. Vindicated, I ordered the new Grignard (actually, I ordered two, the bromide and the chloride). The reaction worked just fine after that.

Now, I don't want to give the impression that I dislike my job. I love my job. I love the people who work with me. I love the project I'm working on. I might not bust out of bed every morning like Spongebob screaming "I'm ready!", but I do hop out of bed and head off toward work and do my job with a big, dumb smile on my face.

However, every so often, a cascade of events affects me in the lab that goes so far beyond absurd that it thrusts itself deeply into the realm of situational comedy. This past week and a half has been one of those eras in my life. See, I've had this compound that we've really wanted to make, and I've made it. Problem is, it's not getting pure. And, I've tried everything. I tried traditional chromatographical ways of purifying it. Still dirty. I've tried recrystallization. Still dirty.
It might not be thermally stable, so I haven't tried sublimating and depositing it. Finally, I decided to work on the HPLC--essentially, a robot whose soul sole purpose in life is to purify compounds. Problem was...when I took my stuff up in methanol (a very polar solvent) didn't fully dissolve. Thinking that I would help it along with a few drops of DMSO (an even more polar solvent), my stuff suddenly crashed out of solution. Yes, I recrystallized my material with methanol/DMSO. My supervisor laughed and said, "Well, maybe we can get a paper out of that..." I took the polar solvents off and tried again. This time, however, I decided to see what would happen if I added water, since the HPLC uses water to purify the compounds.

My reaction essentially puked orange-white stuff onto the sides of the flask.

Heaving a heavy sigh, I shook my head, looked at my friend Joe, and simply said:

"I should have been a cowboy."


Cowguy said...

Cowboys are good. Toby is good. Chemists are good. I got lost with all the alkaline/bromine/turkeydressing/acid stuff. I apologize for not following better.

My lab experience... I spent a lot of time putting vinegar and baking soda in tight containers, when I was young. Oh and I ate a lot of different pills and stuff and smoked some things. :-)

Scope said...

Yeah, the pure ones might give you more prestige with the other boys in the lab, but it's the dirty ones that are more fun to play with.

We're talking chemistry, right?

Melissa B. said...

Or a Cowgirl, as the case may be, huh?

Chemgeek said...

As a chemist, I feel your pain. We've all been there. It sucks.

I always envision the molecules looking out of their flasks laughing at us. They say something like, "Oh, the idiot is going to add water to us. OK, everybody, insoluble precipitate in!!!"

That's why when a reaction doesn't work like it should, I smash it on the floor and stomp on it and yell at it and then piss on it, just to teach those molecules a lesson.

Usually things go much better after that as long as the unreacted starting material has seen or read accounts of my rage in times of insubordination.

It's a lot like religion.

Poobomber said...

Stupid carbon-based things. Or whatever.

Donnetta said...

I'm so confused....

BUT gotta love the mullet - business in the front, party in the back!

Sass said...

I'm not sure about that...

I bet cowboys have lots of chafing in weird places.

I'm just sayin'.

Girl Interrupted said...

Well, in all honesty I didn't understand half of that post.

What I DO understand is that the cowgirl is totally wearing the wrong shoes with that outfit!

And I don't think a cowboy would blog (too busy rustling n stuff and showing off with his lasso) ... so I'm glad you're a chem boffin instead

Cora said...



Soda and Candy said...

I actually really enjoyed chemistry in high school, they showed us all the flashy things like burning magnesium and those quick color change reactions.

The best part was when they taught us how to make sherbet. I think it was confectioner's sugar, citric acid and baking soda.

Good times.

Call Me Cate said...

Cowboys have all the fun. Lab work? Not so much for me. Thanks for playing!

coolred38 said...

Its not too late...since you've no doubt learned some really cool stuff as a you just need to mix that with horsefeed and go get your horse...Im sure you will discover new and exciting things when horse eats horsefeed...just a thought.

Sassy Britches said...

I cheated in high school chemistry.

Ride 'em, Cowboy!

Some Guy said...

I have three words for you: more chemistry posts.

I don't really understand what you're describing, but for some strange reason I find it fascinating to read.

Lisa-tastrophies said...

1. You and Chemgeek are killing me!! I now regret sleeping my way through chemistry (even if the professor WAS hot ;-), because now I have no idea what you guys are talking about and I feel left out :-(

2. I think Scope is right about that.

3. And I think you would make a much more macho cowboy than the semi-gay-porn-rope cowboy in the picture. Plus I would love to see Wizard Cat as you trusty side-kick.

mevans said...

See, that kind of bullshit with the Grignard is the stuff that drives me nuts about professors. Think how much time (and emotional energy) you would've saved if he'd listened to you!

coolred38 said...

Not to mention that Brokeback Mountain is for sure way better than...say...Brokeback Chem Professor...boring.

Hap said...

I thought copper-mediated additions were notorious for being unreliable (did you blink twice? no product for you!), so it wouldn't have surprised that it didn't work, just because.

Considering how not well my chemistry went in grad school, I might have wished to be a cowboy, had I been more physically fit, coordinated, laconic, and pain- and discomfort-tolerant. I don't think that would have gone well.

Ψ*Ψ said...

Much sympathy for anyone who's trying to clean up impossible crud! One of my projects involves nothing but.
Of course, we just got an xtal structure of one of the more promising compounds, and...yeah, doesn't inspire confidence. So the project's dead. Not sure whether to be happy about that or not...

Fancy Schmancy said...

I don't remember high school chemistry, but I do remember freaking my teacher out by writing an excellent paper on lysergic acid diethylamide.

Melissa B. said...

BTW, I'm celebrating One Year in the Blogosphere with a special 2-day Sx3 today and tomorrow. The winner gets a $50 Tar-Jay Gift Card. Please say you'll play!

The Ambiguous Blob said...

Cowboys are the hotness. That is, if you're into boys with 12 words in their vocabulary and in need of a replacement lip because the chaw wore right through their old one.
Oh, and the cowboys I've known don't change their Wranglers near-often enough.

Susan said...

I'm going to run upstairs and read "Chemistry for Dummies". And then I'll be back to re-read the post. But hey, all in all, cowboys rock, ok?

Frank said...

Can't you just show up to work in the lab with a cowboy hat? You may still screw up the reactions from time to time, but you'd look like a complete badass, especially if you could use your lasso to grab beakers and shit off the shelves.

Nej said...

Is your horse named...tttttriger.

D*mn, now that song is stuck, stuck hard, in my head. :-)

I didn't officially take chemistry in high school, I was a physics gal....but I was a teacher's assistant for our chemistry teacher. I took the test at the end of the year for sh*ts and giggles...and got one of the highest scores in the class.

I couldn't talk him into giving me credit though. :-)