Spring Quarter 

Course: CHEM 242 Organic Chemistry Lab 

This was the most rewarding and enjoyable lab course I have ever taken. Throughout the quarter, we completed four experiments: Camphor reduction to borneol and isoborneol, a three step synthesis starting with benzoin (and ending with 1,2,3,4-tetraphenylnaphthalene), an ester synthesis, and an unknowns lab, where we had to figure out what three unknown compounds were (two liquids and one solid). Lab has always been challenging for me, because it was really easy to fall into the trap of just following the lab manual instead of understanding the chemistry behind it. However, this quarter, I was determined to make this lab experience an educational one, rather than a test of how well I can follow instructions.

The first three labs went well. In the Camphor reduction lab, I successfully identified isoborneol as the major product, because the hydrogen in sodium borohydride experiences less steric hindrance when it does an endo attack. The three step synthesis was an interesting experience. We were given five days for a three day lab, but I was out sick for the third and fourth day, so I had to come in on the last day by myself. I felt bad for my TA, Alex, since he had to show up for only one student, but we bonded over music and our experiences in Seattle and UW, all while making 1,2,3,4-tetraphenylnaphthalene. He even came to my band's show a few weeks later! He was most definitely my favorite TA of all time, and I would highly recommend taking his quiz section to any incoming CHEM 242 student. The ester synthesis went by quickly, and I correctly identified my starting alcohol as 2-pentanol. From these labs, I learned how to use the GC-MS software and interpret the results, label IR spectrums, and strengthened my NMR analysis skills. 

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The Unknowns lab was another story. This was the first time I was going into an experiment without much guidance, and I was nervous that I would not be able to figure out my unknown compounds in only nine days. However, after six days, I correctly identified my solid, liquid, and spectroscopy unknowns as benzophenone, 2-butanone, and pinacolone respectively. It took me the first two days to determine that the solid and liquid unknowns were both ketones (+ DNP and - Cerium tests) and then the rest of the days to analyze the NMR, IR, and results of the derivative tests to figure out their identities. I struggled a bit with the derivative tests because my semi-carbazone derivative test kept failing for my solid, so I spent an entire lab period retrying a test that did not work. The next lab period, I did the 2,4-DNP test for my solid instead, and successfully made an orange solid derivative (pictured on the left). I had not originally thought to do the 2,4-DNP test because the semi-carbazone test was supposed to produce derivatives with more distinct melting points but I was fine with this because I was pretty confident my solid was benzophenone due to the aromatic peaks on the NMR spectrum. Since concluding this lab, I am more confident in my ability to direct my own lab experiments and the organic chemistry laboratory seems less scary than it used to be. I got full points on all three unknown reports, which was a testament of my understanding of the chemistry behind these practical experiments. 

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Unfortunately, I lost my 4.0 to a mediocre performance on the second exam despite having scored well on the first exam and aced all my lab reports, but I am still proud of the effort I put into this course and how much I learned as a result. This class showed me that organic chemistry is so much more than reactions on paper; it is a gateway to creating important pharmaceuticals that can benefit millions of people, and for that, I have developed a much deeper appreciation and admiration for chemists.