Canyon Ishikawa, Organic Chemistry at Scripps Research Institute, Week 3

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This week I met with surprise when I came in on Monday and was told that Johnny had gotten sick over the weekend.  This meant that I’d continue my shadowing of Skylar for the entirety of this week, too. Overall though, it was another super interesting week full of learning and more hands-on experience.

On Monday we began running a reaction on a 1-liter scale while several others were finishing up. This reaction in specific took a long time to complete so there was lots of TALKing to check the progress of the reaction to see the separation of the reactants and product. Throughout this time, we were able to run plugs on the smaller, complete reactions. These plugs are small purification systems that use cotton, sand, and silica to hopefully filter out all the impurities and get just the product in the vial (Pictured Below). After all this, at the end of the day we checked the big reaction once more and it still wasn’t done reacting, so we added further catalyst and kept mixing overnight.

Tuesday morning, Skylar asked me to run a TLC (Thin Layer Chromatography) of the big reaction, and there was still starting material on the plate, so it still hasn’t reacted completely yet. We added more catalyst to the reaction and continued with our day. First we NMR’d (Nuclear Magnetic Resonance) the samples that we got from Monday (Pictured Below). With the NMR that we used, you could just insert your samples and leave them running, then the results were emailed to you, so we put them in and waited. All the samples came back and we were able to see that we got the products that we wanted. We then set up reactions for the next day.

On Wednesday I came in and Skylar had figured out that if he used a newer sample of catalyst for the liter reaction, then it fully reacted, so we added that to the reaction and waited on it. Due to all this freetime, Skylar decided that he’d teach me some more “textbook-y” material. He taught me how to arrow push electrons in an equation and how to predict the products of a reaction when given the electrons movement (Pictured Below and in Feature Image). After this we TLC’d the reaction and it was finally complete, so we put it on the rotovap and called it a day.


Thursday we ran a column on the material that we had extracted from the rotovap the previous day. Running a column is where you push solvent through a cylinder with a layer of sand on top, sand with the product in it, and then silica. You then collect the solvent in little vials that hold only a small portion of the total solvent in each. You can then go through and TLC all the vials to see where the product ends up in the whole process. You can then determine that the product is in vials 9 through 17 or whatever the case is. You then put those vials in a flask and rotovap it off. So we did all this to further purify the liter reaction.

Friday was a pretty slow day, but I was able to get off a small-scale column that Skylar gave me full responsibility for. After this was finished, since it was Friday we had a group meeting. Keary, the leader of the lab or primary investigator as his official title is, was gone so we had the meeting on Zoom instead of all gathered in the conference room. We saw a research summary, short lit, and group question.

Other than the lab, I went to Mission Beach on Saturday. Mission Beach was way more chill than any of the other beaches that I’ve visited so far. This Sunday, as per usual, has been just for relaxing and I haven’t really done much today. Also, I figured out how to solve a strange mirror cube with 2 sets of 3 matching sides, pretty stoked on that (Pictured Below).

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