A lesson on electrophilic addition reactions

In the TV series The Big Bang Theory, an atomic model of the helical structure of DNA, a structure of hundreds of plastic balls, stands in the background of the main set for several seasons until it finally, predictably, falls apart in a cascade of colorful balls that pour across the hardwood floor.

The models on the teacher’s desk are nowhere near as complex, but they are just as mysterious to me. They look neat, that’s all the further I get. The teacher holds one of them and in his excitement (yes, excitement) waves it around to underline the most important points of his explanation. He demonstrates how bromine is pushed to the side and the bromine becomes negative and floats away in an aqueous solution. There is an inductive effect, electrons are being lost, the plastic model soars back and forth, the teacher elicits the word carbocation (yes, I looked that up). 

The teacher places the plastic models on an empty desk and turns to the whiteboard. There in 2D marker is one of those diagrams that makes chemistry look like chemistry, Cs and Hs are connected with each other and sure enough the bromine, what else could Br be, looks to be leaving, just as we saw with the plastic model.

“Okay?” the teacher asks. Hats off to the students, they nod as one, they seem content, goodness gracious humans are good at learning stuff. There are only four human students here, kids in their last year of high school. Two want to go to medical school, one is interested in nuclear physics, the other in electrical engineering. How do they know this at 18 years of age?

The teacher passes out plastic models, gives the students a task, and they set to work taking Hs and Cs apart by breaking bonds. “Where does the bromine go?” asks the teacher as the students hold up their models. “Thank god you got different answers,” he adds, “because this is what I’m teaching today.” 

1870. Markovnikov’s Rule. One student has heard of him, a student from Poland. The teacher celebrates. “Yes!” He continues, almost thinking aloud: “Why is it that schools in the former Soviet Union were so good at teaching chemistry? Perhaps because the periodic table was part of the proud heritage of Russian thought. And by the way, why were the Soviets less interested in biology? Because Darwin’s theory of evolution didn’t fit so well with the communist message. And you think science is just facts?” 

So Markovnikov’s Rule. The teacher shares the English idiom about the rich getting richer. He relates it to Matthew 13:12: For whosoever hath, to him shall be given, and he shall have more abundance. An abundance of hydrogen attracts more hydrogen, I think that is his point. The information is coming fast and furious and I can hardly keep up. This is chemistry, but also history and philosophy. It’s been so long, but there were Kuhn and Popper in college, and the unsettling realization that at the top of our human fields of understanding there is a whole lot of debate about how to go about understanding. 

The performance today is masterful. We are watching 25 years of experience compressed into 45 minutes. 

The teacher looks at the pre-med hopefuls. “Do you know the number one reason med students don’t make it through med school?” 

The students laugh. “Organic chemistry?” 

“Right,” says the teacher. “But one time I asked my doctor how much organic chemistry he actually used. You know what?  He rolled his eyes, my doctor, and said ‘not much.’”

He shrugs, a non-verbal it-is what-it-is, the world is sometimes hard to explain. Then he tells the students that he will be on duty in the residential hall this weekend. 

“Come and get free tutoring,” he advises. He walks to the back of the room and sits down behind his desk. I can almost feel the curtains meeting in the middle of the stage, the house lights coming up. There will be an encore tomorrow.

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