ETC: Vonnegut, Djerassi, and a Mystery Polymer

I've recently finished the 1973 novel Breakfast of Champions, by acclaimed science fiction / humor writer Kurt Vonnegut. For those unfamiliar with Vonnegut's work, I enjoy drawing parallels* between him and "chemical provocateur" Carl Djerassi.

These two men share some odd similarities: born within 13 months of one another, each man suffered the Second World War - Djerassi as a refugee; Vonnegut as a POW - and had their personal lives scarred by young, tragic deaths in their families. Nevertheless, both became prolific writers of short stories, novels, and plays, and both lived to be elder statesmen in their chosen careers: Vonnegut to 85, and Djerassi to 91.

I'd even wager that they looked somewhat alike, with their bushy mustaches, well-coiffed hair, stylish clothing and impish eyes:

Novelist Kurt Vonnegut
Credit: Enotes

Chemist and writer Carl Djerassi
Credit: DLD / Stanford

Breakfast of Champions convinced me that Vonnegut may have had more than a passing fancy for chemistry, himself. Consider this hand-drawn rendering of a mystery plastic, ostensibly factory run-off that main character Kilgore Trout has unfortunately found stuck to his feet after wading through a river in Midland City, Michigan:

Credit: Kurt Vonnegut, Breakfast of Champions

Clearly, that's a cyanoacrylate co-polymer - think Superglue - and it seems to be drawn with a dendrimeric A-B-A architecture. I'm guessing that the ethylene glycol spacers (O-CH2-CH2-O) are meant to suggest the foaminess several characters encounter in the novel, that this mystery polymer is "...the stuff f***ing up Sacred Miracle Cave...", an in-book tourist trap overrun by large, odorous brown bubbles.

Incidentally, I love Vonnegut's inference for the continued polymer chain; where we chemists might write n, Vonnegut inserts his time-work "ETC."

Why? I'll let the author explain his philosophy:

"The man who taught me how to diagram a segment of a molecule of plastic was Professor Walter H. Stockmayer of Dartmouth College. He is a distinguished physical chemist, and an amusing and useful friend of mine. I did not make him up. I would like to be Professor Walter H. Stockmayer. He is a brilliant pianist. He skis like a dream.

 And when he sketched a plausible molecule, he indicated points where it would go on and on just as I have indicated them - with an abbreviation that means sameness without end.

 The proper ending for and story about people it seems to me, since life is now a polymer in which the Earth is wrapped so tightly, should be that same abbreviation . . .it is in order to acknowledge the continuity of that polymer that I begin so many sentences with 'And' and 'So,' and end so many paragraphs with '...and so on.' 

And so on. 'It's all like an ocean!' cried Dostoevski. I say it's all like cellophane."

Sometimes you encounter (surprisingly accurate) chemistry in places you didn't expect.
So it goes.

--
*Bonus: Here's Roald Hoffman interviewing both authors in a 1999 piece for American Scientist magazine

The Chemical 'Real Book'

Buying a Real Book is complicated.

For the uninitiated, the Real Book provides jazz charts, including chord progressions, lyrics, and harmonies for gigging musicians playing in bars and clubs. It's something of a badge of honor, like a construction worker's tool belt or the chemist's model kit and beat up copy of March's 3rd Edition.

It's also technically illegal.

Hand-drawn charts from The Real Book

See, the Real Book cobbles together scraps of published music, overheard solos, and lyrics cribbed from cocktail napkins, and publishes them on fuzzy photocopied pages. No copyright information, official publisher, or complex index. Just 400 pages of non-ASCAP-approved* scribbles. But, funny thing: everyone has one, because they're so darn useful. If an audience member suddenly shouts out "play God Bless the Child" or "Mood Indigo," you can just flip to the right page (136 and 242, if you're curious), and go.

I'm amused how often organic chemistry and jazz dovetail together. Something about the overlap between formalized education - scales and chords for the musician, periodic trends and name reactions for the chemist - and free, artistic improvisation jives with both fields. Both have subdivisions, leading lights, and roguish subcultures.

So, I have to ask: Where's the O-Chem Real Book?

You could say that PiHKAL, the "how-to" book scribed by the Shulgins, might be our version. But even that tome has a publisher, typeface, and a copyright! I'm curious about even more clandestine collections of notes, like a longer version of those clipped-together, ragged notebook pages of hand-drawn structures everyone prepares before final exams. Does anyone still have those, and do you use them to inform your lab work? Do any chemistry professors prepare photocopied books that you collect from University Press just before the semester starts?

Real Book Cover

Even if these books exist, acquiring them might be less fun than the rite of passage required to buy my Real Book.* Ten years ago, I walked into a back-alley, nondescript music store. I asked the clerk fairly routine questions, then glanced towards the bound anthologies on the wall. He told me he didn't know, and motioned towards the end of the counter. Money, that I didn't know if I'd see again, went onto the counter. The clerk nodded, and told me to come back in 20 minutes. A paper bag awaited me near the back of the store.

*Coda: Although I own a copy of the book, I don't condone theft, especially of intellectual property. Songs count. When I need actual sheet music for a group or performance, I always purchase it directly from the composer or ASCAP-approved music shop.