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Blog Carnival: What the Cope Rearrangement

Taught Me About Chemistry
by James
in Organic Reactions
Note: to celebrate the International Year of Chemistry 2011, theres a blog carnival going on. This is my
contribution. If you cant follow the structural details, hopefully the story tells itself without the pictures. You can
find the other entries by searching the #chemcarnival hashtag on Twitter JAA
One day in the mid 1990s at some random undergraduate institution, a bespectacled, soft-spoken organic
chemistry instructor wrote this reaction on the board.
https://www.masterorganicchemistry.com/2011/09/26/blog-carnival-what-the-cope-rearrangement-taught-me-about-chemistry/ 1/15
This is called the Cope rearrangement, said the instructor. Its a rearrangement of 1,5- dienes. Im slouching
in the front row of this class and to be honest I dont see the point of this reaction. To me, this looks like the
most useless transformation ever: the product and the starting material are exactly the same. This is not even
flash-card worthy. Little did I know that this useless transformation had a lesson to teach me.
Flash forward several years later : working as a research assistant in an organic chemistry lab. We pack up in a
car and drive across town to see a talk by a prominent organic chemistry professor. Ive been an organic chemist
for like, two weeks, and Im not getting most of it. After the intro, the lecturer begins by saying, We just
discovered a new oxy-Cope reaction. Now, I know what youre thinking wait a second didnt Leo Paquette
do all of those?. Uproarious laughter from the crowd. Killin em! I dont get the joke, but I got the
implication: I was now a part of a community where everyone spoke the same language and had the same
background knowledge, and to fit in, I should know as much about organic chemistry as possible so I can
understand what the hell these people are laughing about. And I needed to learn about this Leo Paquette guy.
Leo Paquette, rocking the anionic oxy-Cope
Several months later, after some courses and a lot of reading, the beauty of the Cope rearrangement was
becoming apparent to me. The reaction we were fed back in undergrad was only boring because the ends were
the same, leading to a degenerate reaction of two molecules in equilibrium. Where the Cope rearrangement can
find use is in systems with a lot of ring strain, which means that one variant will be favored.
Theres even a molecule called Bullvalene, which doesnt have a fixed structure: it spends eternity Cope-ing
with itself. Wild.
Whats particularly useful is the oxy-Cope variation, where an oxygen is bonded on the 3-position of the 1,5
diene. Rearrangement in this case leads to the formation of an enol, which tautomerizes to the ketone. This gives
you about 7 kcal/mol or so, enough to drive the equilibrium forward. The oxy-Cope can be used together two
complex fragments: you can start with an alpha-beta unsaturated ketone, add a vinyl Grignard to it, allow to
warm, and youre done (versions like this where the oxygen is anionic are particularly fast). One of the coolest
variations is when its combined with the Diels-Alder reaction to transform bicyclic ring systems into fused
rings.
For several years, the Cope rearrangement was something Id only read about in a textbook and the chemical
literature. I knew all about it but had never done one: like an exquisite wine that Id read about but never tasted.
About 3 years into my Ph.D. project, I was working with a funky ring system that was behaving strangely. As I
left it in the NMR tube overnight, its peaks slowly disappeared, to be replaced by new ones. The whole process
screamed out unimolecular rearrangement. And to make a long story short, that turned out to be the case.
Wanting to know more about this process, so I measured the integration of the signals by NMR. And I got this
graph.
Its hard for me to explain what a tremendous feeling it was to plug in the numbers and get a graph like this, a
beautiful curve. I know, I know its what youre supposed to get unimolecular decay, everyone learns it in
gen chem. But to get data, fit it in a curve, and get a half-life out of it, that was extremely rewarding. Something
abstract, which Id read about in a textbook, had become concrete and I wasnt following any lab manual or
procedure. It was the natural pattern of the data I was collecting.
I dont think any number of lectures, lab sections, videos, or inspiring lecturers can ever truly capture what its
like to have an experience like this. Its something you just have to discover for yourself. The Cope
rearrangement drove home for me that there is a beautiful order in the way that nature works, and we can
uncover it through recording and charting our observations. And it also inspired me to know more about organic
chemistry so that I wouldnt be left out of the inside jokes.
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Tagged as: awesomeness, cope rearrangement, fun, Leo Paquette, self-indulgence, self-promotion
{ 3 comments read them below or add one }
Curious Wavefunction
What a great post! The Cope is indeed a deceptively simple reaction which hides surprising riches.
Reply
james
Thanks! I was actually going to do combustion, but you beat me to it. Leave it to you to write a post
about the big picture.
Reply
Shreya B.
Thanks James, this is super helpful! Fun fact: Maitland Jones (who named Bullvalene, which you
referenced above) is my current orgo professor. My final is on Tuesday pray for me (your reaction guide
has been hugely useful this week)! SB
Reply
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9/29/2017 Blog Carnival: What the Cope Rearrangement Taught Me About Chemistry Master Organic Chemistry

Master Organic Chemistry

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Blog Carnival: What the Cope Rearrangement

Leo Paquette, rocking the anionic oxy-Cope

{ 3 comments read them below or add one }

Activating and Deactivating Groups In Electrophilic Aromatic SubstitutionPosted on: Sep

The Hofmann and Curtius RearrangementsPosted on: Sep 19, 2017

Reducing SugarsPosted on: Sep 12, 2017

Reductive AminationPosted on: Sep 01, 2017

About Master Organic Chemistry

Copyright 2017 MasterOrganicChemistry.com. All rights reserved

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Substitution: What is Substitution?

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