C2O

I was in the grocery store when the following caught my eye.

Instead of thinking "Oh, that's clever and catchy. Instead of H2O, they call their coconut water product C2O", I automatically thought to myself: "Is C2O a stable molecule?"

When I teach Lewis structures in class, we use examples to build up four general rules of thumb to draw good structures.
1. Octet! (Especially C, N, O, F)
2. Small formal charges (+1 and -1 are okay)
3. If there are formal charges, negative goes on the more electronegative element
4. Resonance helps!
(In class, we actually go through the reason why these general rules work. I'll skip this so you won't feel like you're in chemistry class. The horror!)

So three seconds later, I have thought of the following structure for C2O.

The problem is that there is the carbon on the left does not have an octet. The structure is somewhat analogous to the interesting resonance structures of carbon monoxide (that we discuss in class). Yes, I think about this about ten seconds after.

Both the structures shown are important because even though both atoms follow the octet rule in the structure on the right, the formal charges do not follow element electronegativity. The whole formalism for Lewis structures is interesting because we attempt to statically represent the dynamical electrons to give ourselves some conceptual understanding of what the electrons are on average doing in the molecule. We cannot actually pinpoint the location of any electron to perfection thanks to the real Heisenberg (not W.W. for the Breaking Bad fans). The structure on the left sort of looks like the C2O structure except you cannot use the same "moving electrons around trick" to get octets around each atom.

Then I thought that one way that C2O could be come stable is by dimerizing to form (C2O)2. I've now used up probably about a minute of grey matter.

The octet rule is now satisfied. I don't even know if this molecule actually exists or if anyone has made it.

One that I do know exists is C2O2.

Now wouldn't this be better as a formula for COCO-nut water and make better advertising? I've now probably "wasted" 3 minutes total thinking up all of this while still at the grocery store.

Well, no. Because ethenedione is not good for you, nor is it an ingredient in coconut water. (Thank goodness!) What is in coconut water? Companies advertise this as an electrolyte replenisher so it's really just salt water with some sweetness so you don't spew it out of your mouth when attempting to drink it. And the whole point of C2O is its analogy to H2O in an esthetic and non-chemical sense.

What did I learn from this? That my brain automatically thinks about chemistry given half a chance in most any situation. The first time I read the word "unionized" in the popular press, I read it as un-ion-ized, i.e., a chemical species that remains neutral rather than turning into an ion (an electrically charged species). I was all confused for a bit before figuring out my error. However, every time I see the word, I still automatically read it as a chemist for a split second before I quickly realize that context matters. An even worse example was when the word "staycation" showed up on a headline and I actually pronounced it "stay-cat-I-on" and couldn't figure out what it was and someone else had to explain it to me (after a lot of laughing). Maybe no one else but a chemist will find it as funny.

And thus concludes my possibly useless chemistry lesson for the day, which I have found amusing as I muse upon it. Three minutes of thought. An order of magnitude longer to write down the thoughts and preserve them for posterity. Is this what blogging is about?

Quiz for non-chemists: There should be enough information in this article for you to draw a good Lewis structure for CO2. (Now that's a worthy molecule for a great many posts in the future...)