How to improve your memory through, uh, uh…um…organic chemistry

24 Jul

Just about everyone wishes they had a better memory. Fortunately, improving your memory is easier than you might think.

Let’s take a typical grocery store shopping list: oranges, cabbage, apples, soda, bread, and potato chips.

Should you write it down? Not if you have a basic understanding of graduate-level organic chemistry!

First, look at the list. There are six items. Since 3-methyl-1,2-cycloheptanedione has numbers that add up to six, and since it exchanges the largest number of hydrogens for deuterium when treated with KOD in D2O, you should remember that there are six items you should get at the store.

Next, group the items according to their department; say, oranges, cabbage, and apples are all in the produce section. Now, recall that Jones’ reagent oxidizes aldehydes to carboxylic acids but normally does not oxidize ketones. In other words, an Oxonium Conjugate acid of the Aldehyde, or OCA: oranges, cabbage, apples!

Second, the lithium enolate base from cyclohexanone reacts with alkyl halides, and methyl iodide and tert-butyl bromide react to give different organic products, 2-methylcyclohexanone and a mixture of cyclohexanone. Recall that acetaldehyde with a R 1,2-propanediol (acid catalyst) gives two isomeric acetals, among them conformers like the base for acesulfame, a sweetener used in many sodas. So, soda is the fourth thing on your list!

Finally, 3, 3 dimethylcyclopentylcarbaldehyde and meta-chlorobenzadehyde are enol tautomers of methylcyclohexanone, which, when treated with an excess of cyclohexanone produces an intermediate isotope exchange. Bread and potato chips!

I’m not really sure how that follows. Maybe you should write those last two on your hand.

Finally, what if you get to the checkout but realize you forgot your wallet? Simply throw brevicomin, a bicyclic acetal, into the checkout guy’s face and run like hell!


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