Canyon Ishikawa, Organic Chemistry at Scripps Research Institute, Week 2

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This whole week was largely spent continuing to familiarize myself with the lab and the cycle of reacting, testing, and purifying. During week two I shadowed Johnny for the first three days, and then when he took a couple days off, I shadowed Skylar for the remaining two. Shadowing Skylar was a very valuable experience, as it gave me perspective into another person’s projects and how their methods are different from Johnny’s. Skylar was also great at teaching me the complexities behind the reactions he was setting up and simplifying it into terms that made more sense to me.

 

 

On Monday, Johnny and I started the day by setting up three reactions. These reactions were exothermic (released heat), so to prepare for these conditions we set them in an ice bath. After a couple hours, we TLC’d them (Thin Layer Chromatography, which is where we can test seperation between reactant and product on a thin layer of adsorbent silica through their different polarities) to see if the reaction was complete. It was, so we were able to then load them into the biotage, a machine that purifies the solution by pushing further solvent into a filter that the product sits on and then were able to get vials of pure solution. We then rotovapped them to distill off the solvent and get just the product.

 

Tuesday followed suit, but these two reactions were endothermic (requiring xthe absorption of heat) and also produced nitrogen gas, so to prepare for this we set them in a hot oil bath and used high pressure resistant glass and lids to contain the reaction. We then followed the purifying process. Throughout this process, however, we ran an aqueous workup, which is where we added water to the solution, shook it around, then filtered it out. This just further purifies it, and we could because it is not a water sensitive reaction. We then finished the day by testing if we got the product we wanted by using NMR (Nuclear Magnetic Resonance).

On Wednesday, we ran through this process once more. These reactions weren’t indoor exothermic and did not largely produce any gas, so we could just put them in little viles to run them. To measure out all of these reactions we used these super precise scales that can measure out to a tenth of a milligram (Picture Below). We then went through all the purifying process with one of the reactions, but one of them wasn’t completely reacted yet, so we had to leave it overnight.

Thursday was my first day of shadowing Skylar, so it was a lot of getting used to how he ran things. Skylar runs a reaction on much bigger scales then Johnny. Instead of using tens of milligrams of solvent, Skylar uses liters of solvent to run his reactions. This was a big change, but was pretty fun to be dealing with these big viles and filters. Due to this, the whole cycle is much slower, so it took longer than a day to go through it all. We were able to solely filter the reaction he had already set up the prior day and rotovap (rotary evaporate) it off within this day.

On Friday, we continued this big scale work and only at the end of the day were we ready to NMR our sample and see if we had actually got the product we wanted. These two days were much more hands on and doing things around the clock rather than waiting for things to happen. Also, since it was Friday, we had our weekly lab meeting from 2-4 p.m. Within this meeting there was one “short” literature presentation, one long literature presentation, and three group problem-solving  chemistry questions. The literature presentations are presentations that everyone has to do in a rotation where they find scientific literature and present it to the lab. Skylar happened to be presenting the short literature this week. The group problems are a set of problems that someone creates that looks almost like a test (Pictured Below), and everyone starts off by themselves to try and solve them, then it goes to partners, then everyone joins to present the answer.

Other than the lab I’ve continued to go to the gym after the lab everyday. This filled up my day between the lab and the gym. On Saturday, I for the most part took it slowly as I was a little exhausted, but I then decided to check out Tourmaline Beach because I heard it has good surf. I didn’t surf that day, but it looks fun so I think I’ll return. Today, Sunday, I’ve also been taking it slow, but I think I’ll visit Mission Beach later today.

 

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