Aromatic Rings!

Last Friday in my organic chemistry class, there was a take home test about benzene chemistry due. I, for the first time in memory, had finished the test a day early. So, instead of staying up all of Thursday night in order to finish my test, I made the decision that there was going to be a donut party in class the next day. This is a food pun which I have been resisting since the end of gen chem, and I simply could not hold back any longer. So I whipped out my kitchen notebook, reviewed some of the literature, and began planning my synthesis. I was going to make some aromatic rings!

Don’t you feel like you could go furan aromatic ring right about now?

Method

I based my donut dough on this recipe, which was posted on Vegan Hedonism about a year ago. I always use some variation of it whenever I feel like making donuts. I left out the “egg replacer”, and used all cold soymilk instead of the mixture of water and warm rice milk called for by the Vegan Hedonism folks. The dough was mixed around 8 pm Thursday, fermented it in the refrigerator until 8 am Friday, then sectioned into 3.5 oz round balls of dough, placed on a floured pan, covered, and returned to the fridge to rest/proof. When I got back from my tech writing class at 11 am, I removed the pan from the fridge, and let the dough warm up while I prepped my icings and started heating my oil. When the oil was 375 Fahrenheit and the dough was sufficiently spongy, I stabbed each dough ball through its center, and pulled it out into a nice donut shape. Into the hot oil they went, two at a time. They fry on one side for 90 seconds, then get flipped with a skewer, and then fry on other side for 90 seconds before lifting them out with the skewer onto some waiting paper towels. I like to throw in the next two donuts at this point to get them started, then glaze the first ones while I wait for it to be time to flip the new ones. I glazed half of the donuts right out of the oil, and left the other half to cool so I could dunk them in the thicker frostings. I was in a bit of a hurry when I was frying and decorating these, so I didn’t record the weights of the glaze and icing ingredients I used. I will have to make donuts again some day and document it as a tutorial for you all.

(Transition state)

Discussion

Despite the horrible/awesome mockery of my beloved “food science”, there WAS some real live aromaticity going on in these donuts. All of the icings contained your favorite and mine, 3-hydroxy-4-methoxybenzaldehyde, AKA “vanillin”, the major molecule responsible for the flavor of vanilla

3-hydroxy-4-methoxybenzaldehyde

The pink icing was spiked with benzaldehyde (which is what makes bitter almond extract taste like bitter almond extract).

benzaldehyde

I’ve always been more interested in using food science to affect the structure of bakery foods, rather than the details of flavor chemistry, but now that I’m almost done with this school year of O-chem, flavor chemistry is starting to seem more interesting to me- probably because I can understand parts of it now. Two years ago if I looked at these funny stick drawings, I kind of spaced out. Now, my mind fills with thoughts of resonance, sterics, functional groups, and pKa values. I tentatively think this is kind of cool, but I guess I will have to get back to you on that…

Look! Shiny!

So, all in all, I think its safe to say this synthesis was a success. The yield was 100% and the solvent was able to be filtered and reused, so these are some pretty damn green donuts, yknow?

And the best part is…. Theres only 50 kilocalories[1] per 6.022×10^23 donuts! … And they are “organic”! [2]

[1] About 50 kcal down to cyclohexene, and really I do not feel like going and remembering how to calculate the rest of the C-C and C-H BDEs. So lets just say 50 kilocalories because I’m sleepy. I had a physics test this morning, and have already done all the thermodynamics I feel like doing thankyouverymuch.

[2] Sorry. That wipes out my pun quota for at least a month, right?