Got an email the other day from a student:
“My professor gave me this to help pick out a good tutor. Can you answer it so I can bring it to him? ”
Here’s the quiz.
My second reaction was: this is bullshit.
There are tons of people in this world who could answer these types of questions. If you do a Ph.D. in a good synthetic organic chemistry group, read a lot of papers, do a lot of problems, the knowledge of organic chemistry becomes a part of you.
So what does that have to do with tutoring? Pardon my French, but two words come to mind: Jack Shit, and capitalize both words please.
How many students give a crap if their tutor understands Seebach’s methodology for self-reproduction of chirality? Or the mechanism of the Kulinokovich cyclopropanation? Or Frater alkylation, or the Neber rearrangement?
In the over 1500 hours I’ve spent tutoring students all over North America, how many times have I gone through those topics? Close to zero. Sure, there has been the odd graduate student who’s needed assistance with higher level topics, and on those occasions I’ve relished the chance to bring out some of the more obscure items of organic chemistry flora and fauna that have entered my brain over the past 10 years. But that’s rare.
A deep knowledge of organic chemistry doesn’t make you a good tutor. When I started tutoring, I sucked at it. Really bad. And I probably knew more organic chemistry then, since I was fairly fresh out of a high powered postdoc, and was still spending more time reading JACS than Hacker News. I sucked as a tutor for the first six months or so, precisely because I saw the world through the eyes of a Ph.D. chemist, accustomed to talking to other Ph.D chemists. It took me months and months to see chemistry through a student’s eyes – to see all the little mistakes and misperceptions that students have when they’re learning the subject.. In many cases these were students from community colleges or small schools, dealing with organic chemistry on a really basic level. The reward for spending all of that time was an improved awareness of common student difficulties: the more I became a connaisseur of their mistakes, the better I got at reaching students who were new to the subject.
Nor does the absence of deep knowledge make you a bad tutor. Look at Steven, for instance – he’s not a chemist, and he doesn’t even specialize in tutoring organic chemistry. But he’s a pro at explaining the nuts and bolts of organic chemistry in a way that students can understand. Many Ph.D. level organic chemistry instructors could learn a lot from him.
Knowledge is useless if you lack communication skills. That means understanding your audience. I don’t always succeed, but that’s why I write blog posts about topics like seeing hidden hydrogens, and not the Kocienski modification of the Julia olefination. Because your average student learning the ropes of organic chemistry struggles with all kinds of little issues that many Ph.D’s are blind to, and has to master these before they can grasp the nuances of complex organic chemistry methodology. And that’s what the purpose of this site is – to help untangle all these tiny little issues that Ph.D. organic chemists often take for granted. I know I did.
Yes, of course it’s important to be knowledgable about organic chemistry in order to be an effective tutor. But being able to answer some arbitrary synthesis and mechanism problem is hardly the measure of one.
*In the unlikely event that anybody cares, here’s my answer:
1) tBuCHO, PPTS [formation of acetal] 2) oxalyl chloride, DMF, then TMSSiH, AIBN 3) LDA, –78 C , then acrolein. Separate diastereomers. 4) BOMCl, Et2NIPr. 5) LiOH [hydrolyze ester]. 6) SOCl2, then EtOH. 7) NaH, BrCH2CO2tBu 8) Tebbe reagent.
As far as the second one is concerned: the only answer I can see would be aryne formation, followed by Diels Alder (with benzene !?) followed by retro Diels Alder (forming naphthalene, kicking off acetylene) followed by another Diels Alder of naphthalene with the aryne, followed by another expulsion of acetylene, which gives anthracene. But I don’t really buy it; metal halogen exchange should be faster than aryne formation, benzene doesn’t like to undergo Diels Alders at 25 degrees C, and THF is a terrible solvent for t-BuLi. What’s the yield on this sucker?