First of all, I am extremely happy in Siena as part of the Emory University's Chemistry Studies Abroad Program. So far, this trip has brough nothing but fun and excitement while providing a very unique educational opportunity for us to partake in. Among many of the events that this trip has brought to us within the first week, one was the poster session held by the graduate researchers here at the University of Siena.
After reading much of what you all wrote about the chemistry at the poster session, I came to an astonishing revelation: I actually learned something in school! (Chi, if this is not being humble, then I don't know what is...) But regardless, I realized that all the chemistry that was presented to us at the graduate poster session is just a very specific extension of informaion that we already learned in undergrad.
For example, I took a personal interest in the poster in the field of organic chemistry, which happens to be one of my areas of interest and knowledge. The poster was titled, Photo-Fries Rearrangement of Aromatic Amides as a Tool for the Heterocyclic Synthesis, and it studied a reaction that is usefull in the preparation of a hard-to-synthesize molecule. For the scientific-minded individuals reading this, specifically the reaction extended the use of a photo-fries rearrangement (see figure below) to include aromatic amides as compared to the commonly used aromatic esters. This reaction serves the purpose of providing a useful technique for the formation of aromatic ortho-amino ketones, which are used in preparing various heterocyclic systems.
A general Photo-Fries reaction.
Normally has oxygen in place of "X"
New study works with nitrogen for "X"
After reading the poster, I realized that I knew what the poster was about, the science behind the reaction, reasons why the reaction is important, and I was even able to come up with my own proposal for a possible mechanism for this reaction (which I later Googled and discovered I was partially right!). I actually wondered if the reaction was solely intramolecular or intermolecular, as I could see a possibility for both. I also noticed that data was given that showed the variance in percent yield of product due to changing para-substituents. I figured that the next step in this line of research should analyze the correlation between the lowering of energy of the molecule (via changing para-groups) and the reactivity for photo-Fries, and this can be measured from both a kinetic and thermodynamic perspective. You see... I was able to take my knowledge in organic chemisty and apply it to a graduate research poster that I thought would be so far above me head I would have to work my a** off for another 4 years of intensive sciences to understand. This experience was truly mind-opening and gave me the confidence and the motivation to go study hard and learn as much as I can about whatever interests me (but only after the party that night... and the next night... and the next... and the next...) I mean, get real: what do you think a bunch of intelligent college students would do when given the opportunity to study (as well as get drunk) halfway around the world? Now that's what I call studying abroad! ;)
After all... what more is there at my age than to strive to be an intellectual and enjoy life while I'm at it, eh?
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In reference to your quote:
ReplyDelete"I was even able to come up with my own proposal for a possible mechanism for this reaction (which I later Googled and discovered I was right for the most part!)."
What was your alternate proposal?
my alternate proposal? The main mechanism is a radical reaction (as Jose said today) that breaks off the ketone from the ester and then resituates itself in the ortho position. I proposed a carbonyl attack by a radical on the benzene ring BEFORE breaking off the ketone R group. That part was apparently wrong.
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