Cute, eh? I can think of a number of ways to use this molecule in undergrad chemical education:
Identify the functional groups
Calculate the degree of unsaturation
Name R/S stereochemistry
More difficult problems could be
Name the compound
Predict the products under given reaction conditions
Give reaction conditions that would produce a specific product.
Functionalizing the phenyl ring would be especially good to ask about, since it would reach into resonance stabilization through the alcohol function, possible interference from the cyclopentene double bond.
If I was feeling really mean I’d ask for a retrosynthetic analysis… using only terpenes.
One problem, though. What is this molecule?
It’s easy enough to draw — I just timed myself at 11s. On paper, that is. But naming is a bit annoying, especially since I haven’t really been using the ‘organic nomenclature’ portion of my brain for the last fifteen years. It’s a 1-ol, phenyl, 2-(cyclopent-2-enyl) … propane? Screw this, I’ll look it up in PubChem!
Ten minutes of fighting with the pubchem structure drawing engine reveals that the compound was deposited as (S)-[(1R)-1-methylcyclopent-2-en-1-yl]-phenylmethanol … deposited by the good folks at Nature Chemistry, in fact. Ah yes. Actually PubChem has a convenient link right to the article, from which I can download the Supplementary information PDF, which contains a slightly different name– ((S)-((R)-1-Methylcyclopent-2-enyl)(phenyl)methanol) and a slightly different diagram (with an explicit Me at the 1-carbon of cyclopentene). And if I drive all the way through the full text of the online article (or Google the InChIKey, GZJFLEKXATUYSK-OLZOCXBDSA-N), I can find that this compound actually has its own home page on Nature Chemistry, with a link to PubChem and downloadable representations of the molecule in ChemDraw and mol formats.
I’m not saying this to single out Nature Chemistry, by the way. This is great stuff, and much better than the way it used to be — I am young enough that although I was trained in how to use Chem Abstracts, I was fortunate enough to never need this knowledge.
But what if the article had been printed with a tiny QR code in it, like this: This encodes the InChIKey, from which you can easily do a PubChem or Google search. A chemical structure QR code doesn’t just have to be the InChiKey; a journal could include a link back to the figure or compound’s home page.
Try it out yourself – you scan scan QR codes from your screen natively on an Android phone; with iOS you need to install an app (I use the ‘free’ ad-supported version of Qrafter)
Imagine if you could easily include this QR in every chemical structure drawn in ChemDraw. Imagine if, while going through a stack of reprints or preprints or articles to review, you could easily get to an online structure database and search the literature around a particular compound.