Chemistry is the new Black
Posted by Phillip on Tue 19 Jun 2012Categories: News , Uncategorized | [3] Comments
— What is that chemical?
A couple of years ago, a letter popped up in the Chemistry World inbox, wondering about the identity of a chemical-looking logo on the Technicals line of outdoor gear from UK chain Blacks. General concensus at the time was that it could represent some kind of stylised neurochemical, but strictly the logo looked like a saturated hydrocarbon.
Well, two years and an undergraduate synthesis project later, another letter has arrived…
— Blacks logo synthesis
Mark Cockerton at Plymouth University in the UK took up the challenge to synthesise the logo hydrocarbon. Under the supervision of Simon Belt, Cockerton used Friedel-Crafts acylation of ortho-xylene and two rounds of hydrogenation to reduce out the ketone and benzene ring functionality, leaving the bare bones hydrocarbon ‘logo chemical’ as shown in the synthetic scheme here.
To me, this is a fine example of the importance of communication to science – through whatever channels that happens, and gives me a warm, fuzzy feeling that somehow our original correspondent, the people who commented on the blog and myself have helped inspire someone to do some new chemistry. Not only that, but in doing so, we may have helped guide a budding chemist on the way to exploring chemistry further. In his letter, Cockerton says:
Apart from the satisfaction of making my target molecule, this project gave me first-hand experience in obtaining and interpreting analytical data, especially from IR, GC-MS, and NMR spectroscopy. As an inexperienced undergraduate student, I found determining the identities of all diastereotopic protons of all chemicals made and the conformation of the ‘logo chemical’ particularly challenging, but if this mirrors the real life of a research chemist in any way, then the whole experience has left me craving much more.Good luck to you, Mark, in your further studies and exploration of the world of chemistry. However, there still remains one conundrum – what is the logo meant to represent in the first place? I guess this will forever be one of those unanswered questions…
Phillip Broadwith
Tue 19 Jun 2012 at 2:02 pm
Didn’t they get different products after the first step of the reaction? How did they proceed to separate them?
Thu 21 Jun 2012 at 5:33 pm
Hi Skrith,
I don’t have the full experimental details from Mark, but the o-xylene is symmetrical and my guess is that the position adjacent to the methyl is much more sterically hindered than the one further away, so the selectivity is probably OK, and the electron-withdrawing effect of the ketone in the product should discourage secondary reactions.
Mark did mention that the first hydrogenation did give a mixture of products – he got some alcohol as well as the deoxygenated product.
Either way, a bit of column chromatography should sort most of those mixtures out.
Tue 18 Sep 2012 at 4:26 pm
[...] we’ll talk high fashion. At Chemistry World, Phillip Broadwith noted a neat undergraduate synthesis project: making a hydrocarbon to match a clothing label’s logo. After just three steps, Plymouth [...]