Organic 7/16/21

Science with Richard Bleil

The other night, I had a dream that I had been asked to teach one last organic chemistry class. Of course, in the dream, the number of students registered were so much larger than the capacity of the room that they were lined up in the hallway to get it, and yet, somehow, they all fit by the time the class began. No, in the dream they had not registered because I was teaching it, but rather because they needed the class, and it was the only section.

I really didn’t want to be teaching the class, even in the dream. But, I have taught (in real life) organic chemistry often enough that it was not a problem to just jump right in. The reality is that organic chemistry is one of my least favorite chemistry topics, but it’s the course that, other than general chemistry, I’ve taught most often.

As a side note, one of the students who, in the dream, had registered was a very good friend of mine in Oregon that I have known (quite literally) for decades but had never met. Yes, I mean in real life. My concern was that, as excited I was to finally meet her in person, I was worried about the strain organic would put on our relationship because it is so difficult for so many students.

Organic chemistry has its roots in the Vitalism theory that says that any organic compound can only be made from inorganic elements through the action of some kind of living organism, such as bacteria. This theory was disproved by Adolph von Bayer (yes, like the aspirin) when he created an organic compound from inorganic quite by accident. Reacting carbon monoxide with ammonia under high temperature and pressure, both inorganic compounds, he created the first ever organic compound without extracting it from a living organism. And this breakthrough molecule? This astounding molecule that destroyed the theory that a living organism was needed to make organic compounds? Urea.

Out of about a hundred or so useful elements (meaning they are stable enough to create compounds), inorganic chemistry deals with all but one, carbon. Organic is the chemistry of carbon compounds. It might seem like the simpler subject is organic since it is just one element, but there are a multitude more organic compounds known today that all of the inorganic compounds together. Actually, it’s not even just carbon. Typically, it’s carbon and hydrogen containing compounds. Yes, there are other elements that can be in organic compounds (often oxygen, nitrogen, sulfur but other elements are also possible), but if it has carbon and hydrogen, it’s considered organic. This is why carbon dioxide and carbon monoxide are not considered organic compounds.

So one has to wonder why it is that this one element, carbon, is so unique in that it can form so many different compounds. There are really two reasons. First, carbon forms four bonds. These bonds can be double or triple bonds so it can be bonded to fewer than four other elements, but it (almost) always bonds to at least two elements.

Second, carbon has a very unique characteristic in that when it bonds with itself in a single bond, the strength of this bond is about as strong as when carbon bonds with any other element. Most other elements form very weak bonds with elements of their own type, making single bonds of two of the same elements (except carbon) very unstable, and very uncommon. For example, a “peroxide” has a single bond between two oxygen atoms. Hydrogen peroxide, for example, is H-O-O-H, and is so reactive that it’s excessively damaging to living things. This is why hydrogen peroxide is used as an antibacterial. It literally burns living cells killing them, and yes, it also kills skin cells, although we hope it’ll kill more germs than healthy cells. Fortunately, once it’s done acting, it simply turns into oxygen and water. But most peroxides are so unstable that they are explosive.

Forming four bonds, just as strongly with itself as with other elements, kind of makes carbon the “tinker toys” of the chemistry world. You can link carbons together in chains, making them as long as you want, including branches and even creating carbon rings. Polymers, for example, are typically several hundred carbon units long on the molecular level, or even thousands of carbons long. You have, in your body, a protein called the “Titan protein” that is over three hundred thousand atoms long, and this protein has a hundred thousand side chains as well.

This is why organic chemistry is so complex, so large, and literally so important since we, you and I, are solutions of organic compounds.

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