An Alchemical Snake, a Day-dreaming Chemist, and a Molecule that tried to fail me: Ouroboros, Kekulė, and Benzene

Organic chemistry is not my friend. There are other forms of chemistry and physics that I can handle, but those evil aromatic compounds (yep, that’s what they’re called) were always a little too much for my neural networks to process – a process I attempted, for two long semesters. At the very least, I walked away with a story, and that’s worth something. A story that costs memorizing hundreds of flash cards of molecular diagrams is still worth something (there’s another story hiding here, one about why my professor had two missing fingers, but that’s his story. Luckily, I survived organic chemistry with all my fingers intact…)

There are dreams and symbols  that run through our collective psyches; I personally struggle with what this means. However, there is a symbol that spoke to C.G. Jung, the guy who made dreams culturally relevant: the Ouroboros, the snake eats that its own tail, forming an infinite loop. Here’s his take on it:

“The alchemists, who in their own way knew more about the nature of the individuation process than we moderns do, expressed this paradox through the symbol of the Ouroboros, the snake that eats its own tail. The Ouroboros has been said to have a meaning of infinity or wholeness. In the age-old image of the Ouroboros lies the thought of devouring oneself and turning oneself into a circulatory process, for it was clear to the more astute alchemists that the prima materia of the art was man himself. The Ouroboros is a dramatic symbol for the integration and assimilation of the opposite, i.e. of the shadow. This ‘feed-back’ process is at the same time a symbol of immortality” (C.G. Jung, Collected works, volume 14, para. 513)

Going further back in time, Plato seems to describe an Ouroboros as if it was a perpetual motion machine:

“The living being had no need of eyes because there was nothing outside of him to be seen; nor of ears because there was nothing to be heard; and there was no surrounding atmosphere to be breathed; nor would there have been any use of organs by the help of which he might receive his food or get rid of what he had already digested, since there was nothing which went from him or came into him: for there was nothing beside him.” (Plato, Timaeus)

Digging into the remote past, we arrive at the Egyptians…but that too, like my chemistry teacher’s missing fingers, is another story, for another day.I need to move on to why this damned snake tried to fail me.


August Kekulė.

The man who sank a million pre-medical student’s ships. All from a day-dream: the dream of organic chemistry; the dream of the Ouroboros, and the benzene ring:

“I was sitting, writing at my text-book; but the work did not progress; my thoughts were elsewhere. I turned my chair to the fire and dozed. Again the atoms were gamboling before my eyes. This time the smaller groups kept modestly in the background. My mental eye, rendered more acute by the repeated visions of the kind, could now distinguish larger structures of manifold conformation: long rows, sometimes more closely fitted together; all twining and twisting in snake-like motion. But look! What was that? One of the snakes had seized hold of its own tail, and the form whirled mockingly before my eyes. As if by a flash of lightning I awoke; and this time also I spent the rest of the night in working out the consequences of the hypothesis.” (qtd, Read, John, From Alchemy to Chemistry)

And so, in one fell swoop, August Kekulė changed the entire scope of human knowledge. We literally wouldn’t be living in our current age of technology without his insight; in many ways, it’s a Eureka! moment that rivals the discovery of another spiral, that of the double helix that underlies the biology of all living beings.

Some have questioned his story, and that’s fair enough. He might have made up his dream as an anecdote, or even as as a joke. For some rationalists and skeptics, it’s a matter of philosophical integrity to debunk the idea of a dream actually wrapping itself around a scientific discovery…like a serpent…(and somewhere, James Randi is rolling his eyes).

Whatever Kekulė’s motives were in ascribing his insight to a dream, there’s one thing I know for sure:

That damned snake didn’t want me to pass organic chemistry.

(Luckily for me, I manged to slither through)


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