Posted on behalf of Sugar Daddy

Sorry for my extended absence. I was reading some old posts in the Skeptical Chymist for inspiration for today’s post, and I found one by Catherine that encourages us to name more chemical reactions after people. In the post, she further asks whether we would prefer to have a reaction or a football stadium bear our name. I’d like to take that one step further.

If I discovered a new reaction, I would like to sell the naming rights to a corporation. There are many benefits – good press for the company for supporting basic scientific research, excellent promotion for the inventors of the reaction, and of course, most importantly, a much-needed income supplement for the graduate student inventor so he/she can put food on his/her table. There are some good candidate reaction/company partners already available:

The Henry reaction (“O’Hungry?”)

The Suzuki coupling (“Driving aryl-aryl bond formation since 1979”)

The McMurry coupling (“Would you like a side of TiCl4 with that?”),

The Huisgen [3+2] cycloaddition (“Buy the LEGO “click” kit today!”),

And, of course, the Corey-Bakshi-Shibata reduction (“America’s most-watched enantioselective reduction of ketones to secondary alcohols” – I think that slogan might have to be improved, but it can’t hurt too much – they are already trailing NBC and ABC quite badly in the 6 o’clock news ratings anyway.)

Any further suggestions?

Posted on behalf of Retread

The Scandinavian Goddess I had a crush on all through high school could pick up any instrument and play it — piano, clarinet, guitar, saxophone, etc… She didn’t think it was a big deal, it was just the way she was. The Hungarian uprising of ’56 occurred while I was a freshman in college. A friend who already knew 12 or so languages picked up Hungarian in a week or two and went up to Camp Kilmer in New Jersey to act as a translator for the refugees. It was just something he could do. 50+ years later, the 16 year old high school student auditing an upper level college course in abstract algebra I was taking looked up occasionally from his German homework when the lecturer made an obscure point. He blitzed the course and later went on to college.

I don’t think there is anything remotely like that in organic chemistry, although the rumor back then was that Woodward knew all of Beilstein before he hit puberty. Learning organic chemistry always seemed pretty easy and intuitive to me (even now when revisiting it years later). Perhaps it was playing with TinkerToys as a kid. I’ve found math much, much harder.

In organic chemistry you come to know carbon inside out and at least one atom of it is always present, so you can bring everything you already know (which is quite a bit) to the problem at hand. Math isn’t like that at all. You are always bumping up against new definitions, concepts and theorems. Once you get past the plug and chug part of math (use the chain rule n times, integrate by parts m times to find an integral, look for a recursion formula by repeatedly differentiating) you are proving theorems. Here, you must bring everything you know about math to proving the theorem or problem at hand. You may have to create a function, a group, an ideal to solve it, reason by contradiction, think of a counterexample etc., etc…

Is anything like that in organic chemistry? Of course there is. The theorems of organic chemistry are its syntheses. Every reaction you ever heard of comes into play, new ones must be invented, mechanistic pitfalls considered, conditions carefully adjusted etc., etc… You are not asked to synthesize strychnine as a college junior but you start proving theorems in math at that point and never stop. That’s why math is harder (to learn).

So math is harder to learn, but organic chemistry and math are equally hard to do. If we really understood mechanism and reactivity, we could just write out the steps and have a robot perform them. We don’t because our knowledge is very incomplete. In this sense, organic synthesis is actually harder than math, because in math you are starting with a huge background of solidly proven results which are at your disposal. In chemistry you have a similarly huge background, but there is no guarantee that any of it will work on your particular problem. It’s your job to figure out why something which should have worked didn’t do so and a way around it as well. That’s not easy at all.

Retread

Posted on behalf of Mushy:

One of the reasons which drew me to the physical sciences and maths was the inherent, cold, emotionless objectivity. There was right or wrong; black or white. No matter what my lecturers’ views on me, all I ever had to do was write down in an exam what they’d told me in the previous year, and I’d get top marks. Easy as that. Right was right.

Fast forwarding to postgraduate studies, when armed with a clean, fully-assigned NMR and a sensible mass spec, it was a piece of cake to go into a meeting, basking in the warm, hazy glow of certainty that no matter who was in the room, the facts would speak for themselves. I had made what I intended, and woe betide anyone who differs. I was right. The facts were there for anyone to see, criticise, and then ultimately to agree with me. [In truth, none of that happened very much; I was a dreadful synthetic chemist. My NMRs were seldom clean, often shoddily-assigned, and my mass specs mostly laughable. But I digress – that’s all for a later post]. Right—for the most part—was still right.

Fast forwarding further, I found myself in the Big Wide World, and the crutch that had borne the weight of my hubris over the past eight years of university was suddenly whipped from under my shoulder. All of a sudden, right as I needed to be, potentially, it could mean nothing. With a receptive ear further up The Company Hierarchy, my words would be heard, my judgments considered, and my recommendations acted upon. If the ear was less receptive, however, I could find myself in a completely foreign place. I had never before been in the situation where I could prove conclusively that what I was saying was right, that I had a surfeit of evidence, and yet it could mean nothing. No matter what I said, or how I said it; the evidence I produced, or how I produced it, I was completely unable to prove myself right. As a recovering scientist, this was anathema to me. In all honesty, it still is. Gradually, I had to transform from being the analyst I was at university, into the salesman I needed to be in order to get across the ideas which I though were correct. I no longer dealt in cold, emotionless, fact. I was now a purveyor of warm, fuzzy, dangerous perception. Right—all of a sudden—was only what my boss perceived it to be.

Of all the culture shocks to have hit me throughout my slow and ongoing transition from scientist to whatever-it-is-I-do-now, not being able to trust just being right is the greatest, and by orders of magnitude. Being a chemist was—for the most part—great. Working in the City is—for the most part—great. In order to jump between the two, however, it has been necessary to subdue a few of the preconceptions I held dear, and to try to assimilate a whole new bunch of concepts which—useful as they are—are not as black and white.