How (Not) to Find A Good Tutor

by James

in Teaching

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 first reaction was actually, “uh oh, it’s been too long since I did problems like this, I hope I’m not too rusty.” But then I sat down and worked through it.(* below*)

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?

Related Posts:

{ 5 comments… read them below or add one }


You got me with the “Frater alkylation”…never heard of that one. :-)

In all seriousness, excellent post. One of the hardest things for me to remember is that the things that motivate me are not the things that motivate students. What I find cool because it fits in with what I already know (e.g., Mannich = glorified aldol), students will see as a brand new beast. This is true even if I tell them “Mannich = glorified aldol” in class…it’s jsut how the brain works!



I worked in a lab where people did Frater alkylations to form quat carbons… it’s pretty obscure.

Agreed on the later. I can point out patterns that are obvious to me (by now) to students and expect them to say “aha!” immediately, but I sense that it still takes some repetition in order for them to “get it”.


Bryan Sanctuary

Well of course this is not restricted to organic chem. Try teaching physical chemistry to students who 1. do not have/like the math, 2. and do not realize that the math gives the visualization of the microscopic (no other way–all your organic mechanisms are based on this). It is extremely hard to teach students physical chem when they think that all they need to do is remember mechanisms in organic, inorganic, materials, nano etc. One of the common questions about my physical chem courses are: “What do I need to memorize for the exam?” I usually say nothing, you have to understand it. That answer is not popular.

Frequently students come back to me in later years and say that they wish they had realized the importance of the basics when they took physical chemistry.



That’s true. Also, since you’re dealing with a classroom, you have an additional tough decision to make. What portion of the students you are most willing to alienate? If you go slow, explaining every concept in detail, repeating constantly, you won’t have time to get to more advanced material which is the basis of further courses (which the more advanced students will need to take).


Maurine Pen

Great Post! No matter what is said I still do think that generally tutors are great and they are really helpful for students like me don’t understand some topics. I even tried to have a tutor via skype at to help me out. I learned a lot and I am grateful for their help so I hope tutors out their would also do their best at teaching their students.


Leave a Comment