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Mr. Hexane

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 than the molecular biology stuff that I was beginning to get tired of. After all, my roommate seemed pretty happy 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 introductory lab sections I had previously taken. Excited, I dove straight into synthesis — my two projects being the synthesis of Aspartame (better known as NutraSweet) which was, incidentally, discovered by a guy doing random amino acid-like fragment coupling who just happened to lick his unwashed hands (not something I’d recommend) and the Wieland-Miescher Ketone, an interesting chemical structure which is used to synthesize taxol (a potent anti-cancer drug) and other hormones.

Excitement is not the same as skill, however, and, perhaps unsurprisingly, I was a very poor synthetic chemist. An illustrative example of this was during the Aspartame synthesis project. One of the steps of the project entailed azeotroping away acetic acid (what makes vinegar vinegar-y). Acetic acid does not readily boil off or evaporate, but heptane (C7H16) does and because heptane is known to azeotrope well with acetic acid, 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 C6H14 (not heptane), and, while in principle, hexane and heptane can sometimes be good replacements for one another, it did not work quite so well — 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”.

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