The Organic Challenge 3/28/23

History of Richard Bleil

Yes, the FBI knows me.  I’m sure they’ve known about me since I lived with my friend Kosta and his family.  Kosta was not a favorite of the FBI’s because of his association with Russians like General Miltstein, but he also published national secrets.  In the ‘80’s, he was the one who figured out and published the fact that, at that time, US spy satellites had a resolution of at least one square inch.  They wanted to arrest him, but he pointed out that a highly touted treaty with the then Soviet Union was made publicly available, and two parts in that agreement, when taken together, would mean that the US must have such a resolution for the treaty to be verifiable.  Nothing came of it since it was a part of public record (for anybody to put the pieces together), and it resulted in nothing more than a very funny comic strip featuring a penguin picking his nose from a top-down view. 

Not many years later, I would get back on their radar for my very own actions.  It would have been the turn of the century, and I was teaching organic chemistry.  The first semester, required by a few majors, was taught every year, but the second semester wasn’t required in many majors at all.  As such, it was offered every other year, and the class was always small because, for the most part, it was only required for chemistry majors.  The first time I taught it, there were only three or four students (I don’t recall exactly; I mean, it was a few years ago).  Because of university policy requiring a minimum of ten students in a class, I wasn’t paid for teaching it, but had no choice as some of the students needed it to graduate (yes, I cared more about the students than the administration did). 

Now, of all of the chemistry subjects, organic chemistry is my least favorite.  It’s probably because when I had it, I had to pay for a very expensive twelve-hundred page textbook, and all they said was, “memorize this, we’re having a test.”  I am not good at memorization, and in my opinion, you don’t really learn anything when you do so.  It took me a full academic year, but by the end of my organic course, I realized that it may be organic, but it’s still chemistry.  A good deal of the memorization could be eliminated if I simply understood what the compounds were doing using the principles from general chemistry (later I would take a course called “Mechanistic Organic Chemistry” which taught us exactly what I had learned on my own in that year).  So, I decided to teach my organic chemistry a little bit differently.

I always told my students what they should memorize if, indeed, they would be taking standardized exams like the MCAT, but I taught my students, in the first semester, how to learn organic chemistry.  We went through the chapters, like a regular organic course, and I covered the functional group, how to make it, what it can make and what its properties are, but I taught them how to figure it all out.  By the second semester, I did something completely different.

There was (and may still be) an organic chemistry challenge site.  It listed compounds that mostly pharmaceutical companies wanted to make, although they never said why.  They offered rewards, to, up to $100,000.  Mostly it was for organic chemistry majors and post-docs to do for fun, but I saw this as a great opportunity for my students to see how real organic chemistry works.  I never expected any of them to actually win the prize (and they didn’t), but they knew that these were real-world problems.  I had them choose one of the challenges, decide on a reaction pathway to actually make it (which needed my final approval), then make it and analyze it to see what they got.  They didn’t need to get the exact compound, but they needed to figure out what they produced. 

Now many of these organic reactions start with what are called “precursors”.  These are organic compounds with similar structures that can be modified in some way to get the necessary compound.  As it turns out, illegal drugs and other compounds that are on the naughty list can be made from many of these precursors.  More than once, after ordering some of these reactants, I would receive a fax from the FBI that said, “Bleil, what in the hell are you doing?”  Of course, the quantities I was using was not enough to try to sell it (or even use), but it was still fun to see that I could raise an eyebrow in the government.

This was a true learning experience for my students, and there is no doubt in my mind that they learned more from that than me standing in front of them regurgitating information that was already in their textbook. 


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