Marie Wu

For our final project in third quarter Honors OChem, we decided to make ibuprofen. It didn’t seem so difficult from the paper we read: a reducing step, followed by a substitution, and then carboxylation via a Grignard reagent. The first session went well, and we walked out with high hopes, working far ahead of schedule and having finished both of the first two steps. The second session was when things started to get rocky. Turns out, Grignard reactions are awesome when answering synthesis questions on a test, and not so awesome when actually trying to carry out in a lab with only college-level equipment. We spent most of that four hours staring at our round-bottomed flasks, laughing as we tried to figure out exactly what “vigorous foaming” meant and why we weren’t seeing it. The next time we attempted it, we got stuck trying to figure out how to bubble one liter of carbon dioxide gas through the mixture under air-free conditions. I remember laughing as Austin ran back and forth between the carbon dioxide canisters with a balloon and tried to figure out how to get said balloon onto the drying tube, before we figured out that dry ice would be easier to use. We never did manage to make ibuprofen with any more success than the wonderfully high 0% yield, even though we put all of our very best efforts into scrounging up every possible white fleck at the bottom of our flasks. But it’s okay - all the fun we had made every single failure absolutely worth it.