A Modest Proposal

by James

in Conformations, Organic Chemistry 1

Right around this time of year, tens of thousands of organic chemistry students are learning about the cyclohexane chair.

It looks like this:

It’s more of a deck chair than a wingback. See why we call it a chair? It’s got a “headrest” and a “footrest”? The cyclohexane chair form is more stable than flat cyclohexane, because if you look along any C-C bond of cyclohexane you will see that all the carbons are staggered.

On the opposite side of the energy spectrum is the bête noire of cyclohexanes –  known as the cyclohexane “boat”, less stable than the chair by about 6 kcal/mol.  It looks like this:

In the boat form, we have two eclipsed C-C bonds and also potential “flagpole” interactions through the “prow” and “stern”.

In my opinion, the case for calling this a “boat” is pretty weak. Would you really want to take a ride in this unseaworthy-looking vessel?  The S.S. Minnow looks like a luxury yacht by comparison.   Furthermore, since chairs and boats have nothing in common, in order to discuss them together textbook writers have to contrive situations like the one below.

(Nice “boat”, loser! )

The only good thing I have to say about the boat is that it makes a good joke for t-shirts.

Therefore, I have a modest proposal.

Look at the chair again: if you took the “footrest” and made it a “headrest”, what would you get? A hammock!

Makes sense right? Now we’re comparing two similar things – chairs and hammocks. Very clear.

Also, in a hammock, the headrest and the footrest both point in the same direction, and can therefore be close together in space. And if you were to drape your arms and legs while lying in a hammock, you’d see that they would each be straight down –  in the “axial” position. (Don’t try that with a boat. That sucker would sink in a heartbeat).

Therefore I modestly propose that the cyclohexane boat be renamed the cyclohexane hammock.

This is brilliant idea whose time has come. Who’s with me???

 [MY HAMMEC RULEZ]

Image source for Chair Girl/Boat Dude

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{ 3 comments… read them below or add one }

Trish

Then what are we going to call those flagpole hydrogens…..

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james

Well, maybe imagine the hammock is hung between two flagpoles?

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Dave Blackburn

I totally agree. Too bad we JUST finished this topic. Time to modify the handouts for next year.

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