Final Post: Summer Reflection

Summer research was an experience that I will never forget. There were times when it was difficult or frustrating but all the things I learned were incredible and I am so thankful I was given this opportunity. Being able to work for nine weeks straight on my project gave me a much deeper understanding of my specific reactions as well as the background literature relating to my research. I was able to acquire positive results that will allow me to keep moving forward in the fall.

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Week 7: New addition and dehydration reactions

This week the focus was on trying addition reactions in order to move the current product closer to one of our goal molecules. The first two reactions were run next to each other. One was a grignard addition using isopropyl magnesium chloride and then other was an organolithium reaction using n-butylithium. The grignard, which had been run once before on a smaller scale, was run using ether as the solvent instead of dichloromethane. This reaction did not actually occur on the larger scale and we think it is because the solvent could not get the starting material completely in solution. However, all the starting material was recollected so nothing was lost from this trial.

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Week 6: Primary Reactions and Optimizing Yields

The focus of this week was to optimize the original reactions, using all previous runs and yields to determine the reaction conditions. The first dibal reduction was run with standard conditions in dichloromethane. This reaction gave a 50% yield of the desired aldehyde which was higher than previous trials. The TLC taken while the reaction was running was difficult to read because both the starting material and product have limited UV activity and do not stain well on the plates. However, enough product was made to move forward with the aldol condensation. Since the starting material will not react with the next reaction, the product was not purified

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Week 5: National Organic Symposium and past Reactions

The work on my project was a little different this past week. Instead of being in the lab, my professor took our research team to the National Organic Symposium at Indiana University. We arrived on Sunday and that evening, I presented my research thus far with my research partner at a poster display. It was a great experience in talking through the chemistry and reactions that we are doing. Also, we were able to talk to many other professor about what we had done and what problems we had run into. It was helpful to not only be given suggestions but also to be asked questions that made us think about things in a different way.

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Week 4: Reaction Modifications and Results

The reaction results of my fourth week have displayed results that will allow the reaction conditions to be changed in order to be the most efficient. It was observed in the previous week that there is a dominant isomer that makes the cyclization more efficient. This week, that same pyrrole condensation reaction was run on the mixed isomer product as well as the dominant pure isomer in order to gather more information regarding their reactivity. The results provided some important observations, but more trials are still needed to completely understand.

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