Six Word Saturday, the Second Coming

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 was...it 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)...it 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."