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Mr. Hexane

Date: (Spring 2005)

There was a semester where I considered going into organic chemistry. Why not? I had liked the orgo classes I had taken. The subject matter, at least from textbooks, seemed fascinating to me — using the properties of Carbon, Oxygen, Nitrogen, and my other friends from the periodic table to either construct or understand molecules of industrial and biological importance — and it seemed so much more creative-driven and less luck-driven than the molecular biology stuff that I was beginning to become disillusioned with. I mean, my roommate seemed pretty content with his Chemistry major.

So, I took Chem135 — Experimental Synthetic Chemistry, a much more advanced and realistic look at synthetic organic chemistry compared with the intro lab course in organic chem. All excited, I dove straight into synthesis — my two projects being the synthesis of Aspartame (aka NutraSweet) which was, incidentally, discovered by a guy doing random amino acid-like fragment coupling who just happened to lick his hands (which were not washed), and the Wieland-Miescher Ketone which is an interesting chemical structure which is used to artificially produce taxol (a potent anti-cancer drug) and various hormones.

Given that I’m not currently a synthetic organic chemist, one can conclude that the experience showed me that I didn’t have what it takes to go down that path. Basically, I was not a good experimentalist when it came to synthetic chemistry. A good illustrative example of this was during the Aspartame synthesis project. In the middle of that project was a step which required azeotroping. Azeotroping is described in more detail by wikipedia, but long story short, the reaction mixture contained Acetic Acid (vinegar) and we needed to get rid of it. Acetic acid does not boil off or evaporate readily, but heptane (C7H16) does and because heptane is known to azeotrope well with acetic acid, as in a mixture of acetic acid and heptane will boil/evaporate together well, one can eliminate the acetic acid by adding heptane.

I, the brilliant and attentive budding scholar that I was, made the mistake of adding HEXANE (not heptane) C6H14. And, while in principle hexane and heptane ought to be good replacements of one another, it experimentally did not work quite as well as one would hope — necessitating me to evaporate off an extra four equivalents of heptane. D. Zhao, wonderful friend that he is, hence dubbed me Mr. Hexane — and from that day forth, I labeled all of my tubes and flasks and vials “Mr. Hexane”.

And I never lost or misplaced another flask.

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