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Ok...what's a ketone?

May 5, 2007

I tutor for a little extra money. It's mostly beer and video game money, and it's all tax free since I mostly free-lance (I do also work through an agency, which is shifty as they took me 18 months to convince them that yes, indeed, I do have a master's degree from a university you might have heard of once or twice and I should be getting paid for that level of 'expertise'). A while ago, I started tutoring a friend of my wife's. She's enrolled at NC State and, after going through general chem and analytical chem, we've been doing organic since January. Thusly, my comfort level with the material has gotten much better, understandably.

Well, today we were reviewing for the final on Monday, and (of course) the best way to review for a final in organic is to go over all the reactions. Well, we hit up alkynes and went over the reaction using mercury to transform the alkyne into an enol and then tautomerize into the ketone. I got her to the point of drawing out the enol, and then gave the little lecture about how they're unstable and drew out the mechanism for the tautomerization, and I finished with "...and so you'll get a ketone as the final product."

That's when she responded with, "Okay...what's a ketone?"


Here now, let me backtrack a bit. This girl is anything but an idiot. I've never seen anyone (your's truly included) who could translate a Newman projection into the line model so quickly. She's quick to pick up on any concepts and is good at applying them. This is anything but her problem. The professor hasn't told them what a ketone is yet. We're halfway through the book and we haven't hit on ketones??? I came out of high school knowing what a ketone was, it's true, but my organic prof in undergrad taught us all the IUPAC nomenclature in the first week of the course. I think it's inexcusable to allow your students to not know the difference between a ketone and an aldehyde at the end of the first semester. But, this goes beyond that. They don't even know what a ketone is! Ridiculous.

Later, I was going over the difference between activating and deactivating substituents on a ring (since he couldn't be bothered during class...but it will be on the final!) and I was trying to list off what the o,p-directors are as opposed to the m-directors. I said "Ethers are very ortho-, para-directing, and they'll usually go para- first due to sterics."

"I see. Now...what's an ether and what are sterics?"

I realize this is a young professor in his first teaching position, but I think maybe, just maybe, you got your eggs in the wrong basket when you spend half a lecture period telling about how chlorofluorocarbons are bad for the environment and why (because THAT hasn't been hammered into our heads since the 80s) and yet you haven't explained a simple thing like sterics.

Now, I realize I shouldn't complain; so long as this guy keeps "teaching", I stand to make a pretty penny. I can keep myself in long, drawn-out RPGs for years. The other is, I'm not teaching, so I'm not doing the work of preparing the lectures, the homeworks, and dealing with all the students who come in and complain about how nothing in the lectures and homeworks prepared them for the exam. I realize that, as much as they're dogged for being inept and lazy and glorified babysitters, teachers DO actually work and work hard. It's just not usually seen as being hard work because they're sitting in their comfortable chairs bleeding red ink all over some kid's proposed mechanism featuring six bonds to carbon (sometimes known as hedgehogane). But could, possibly, touch on some of the more important aspects of the subject you teach, such as what certain functional groups are, how to describe them, and what happens when you have a t-butyl group on cyclohexane. Yep, you guessed it: never heard the terms "1-3 diaxial interactions".

I think out there, somewhere, Marye Ann Fox just shed a tear.


Ψ*Ψ said...

That makes me sad. Very, very sad. Reminiscent of the descriptive inorganic class I just took where we spent weeks talking about global warming and solubility of salts in water but didn't cover HALF the material we were supposed to.
Fun fact: Excimer named his cat after C60.

the iNDefatigable mjenks said...

Oh that makes sense. I was getting C60 and the name of the cat from Get Fuzzy confused (hence the confusion in one of the comments sections on CBC)

Chemgeek said...

Wow, you just touched on a lot of things I want to comment on.

#1. I use Mary Anne Fox's (and James Whitesell) organic text. I like it because chapter 2 and 3 is all about functional groups. It covers nomenclature, physical properties, hybridization etc... I am a big fan of her text. It is laid out in a similar way to how I learned organic.

#2. As an Organic Chemistry prof, I am amazed/flabbergasted/shocked/astounded, that they had not gotten to a ketone. I am a big NON-fan of introducing functional groups only when covering the respective reactions. Ugh, I couldn't think of a worse way to teach.

I've described organic chemistry as being similar to writing. When you first start out you need to learn what words are. Then you must learn what a noun and a verb are before you can start writing sentences. Once you learn the sentences, then you can write paragraphs and eventually chapters and finally books.

You can't learn to write a sentence if you don't learn what a verb is. Likewise, you can't appreciate or even do organic chemistry if you don't know what a ketone is.

#3. Teaching is hard work. It is a lot harder than I ever thought it would be. I realize now, this is a 12 month job crammed into 9 months. The temptation is always there to give a little less, but I cannot and I will not allow my students to leave my class not knowing what a ketone is or an activating group is. I do not profess to be the best professor around (like the play on words there?). I've been teaching for 10 years now (minus a few for a little PhD work). Every year I get better and laugh at myself for how bad I was when I started, even though I naively thought I was the best back then.

That's enough.

Does Fox still teach Organic at NC State?

the iNDefatigable mjenks said...

I used Marye Ann Fox and James K. Whitesell's book in undergrad, too. I still use it. It has a very nice chart on the inside back cover that gave the pKas of most important functional groups. I was really surprised to find that she wasn't using Fox and Whitesell's book, as she's going to NCState.

I feel (and this is personal) that functional groups should be introduced early on, like on the Wednesday of the first week. Monday should be the definition of organic chemistry, it's uses, applications, and start going over the basic names of the chains. Wednesday should be functional groups and so on. But that's just me.

I just wanted to reiterate, I'm not dogging teachers. It's not an easy job. I considered it for a while both while in grad school and then when I got laid off at my first job.

Marye Ann is now the chancellor or president or something of San Diego State or San Jose St. I'm not sure which. The chemistry building at State is named after her. I considered going down to get my book autographed by her before she left (a bunch of my students at Notre Dame went to Purdue one weekend when I was a first year to get Loudan to sign their books...he called up Marvin Miller laughing over the whole thing).