"This post, dear reader, is 100% about cats."

December 5, 2012 11:31 AM

Screw organic chemistry, I'm just going to write about cats. James Ashenhurst uses (sometimes highly unorthodox!) cat pictures to explain topics in stereocatmistry, starting with On Cats, Part 1: Conformations and Configurations.

The full series:

On Cats, Part 2: Cat Line Diagrams
On Cats, Part 3: Newman Projections
On Cats, Part 4: Enantiocats
On Cats, Part 5: Enantiocats vs. Diastereocats
On Cats, Part 6: Stereocenters
On Cats, Part 7: The Fischer Projection
On Cats, Part 8: Moe the Meso Cat

posted by beryllium (43 comments total)

Loving this, thank you.
posted by Scientist at 11:39 AM on December 5, 2012

Thanks to flex for helping me with this post, and to koeselitz for jogging my memory!
posted by beryllium at 11:41 AM on December 5, 2012 [1 favorite]

This is great.
posted by rmd1023 at 11:44 AM on December 5, 2012

I've heard before that organic chemistry is some special kind of academic torture, but I don't understand why.

What makes it worse than Chemistry as a whole?
posted by Egg Shen at 11:45 AM on December 5, 2012

There's not enough awesome on the internet to ascribe to this.

(Organic chem came really easily to me, maybe that's why I think this is so great.)
posted by k5.user at 11:45 AM on December 5, 2012

This is the best possible way to learn about Chemistry. It's not all cations, but it might as well be!
posted by GenjiandProust at 11:45 AM on December 5, 2012 [2 favorites]

I believe this is exactly the kind of information that should be on Metafilter.
posted by blurker at 11:49 AM on December 5, 2012 [2 favorites]

Best (& most random!) thing to come out of a Nickelback parody thread, bar none.
I don't know anything about organic chemistry, but teaching with cats totally sells me on learning more.
posted by flex at 11:51 AM on December 5, 2012 [1 favorite]

Do not make me learn Chemistry! Do NOT make me Learn Chemistry! DO NOT MAKE ME LEARN CHEMISTRY! DO NOT MAKE.... awwww cats....
posted by HuronBob at 12:03 PM on December 5, 2012 [3 favorites]

Some people might point out that “conformations” and “configurations” are also concepts in organic chemistry that mean much the same thing, and that this post is a thinly disguised effort to teach concepts in organic chemistry through a discussion of cats.

Horseshit. This is 100% cat content here people! This is a cat blog.

Oh, thank god! I was afraid I might accidentally orgo! But whew, just cats!
posted by rtha at 12:04 PM on December 5, 2012

Cute, but there is an obvious problem with this approach.
posted by ChurchHatesTucker at 12:09 PM on December 5, 2012 [6 favorites]

See, and I was going to tell you "that link totally needs to be a post." Awesome.
posted by koeselitz at 12:15 PM on December 5, 2012 [1 favorite]

Argh, not even cats can make me interested in studying organic chemistry for more than like five minutes at a time.
posted by Scientist at 12:19 PM on December 5, 2012

Software Engineering, Now With Cats!
posted by Artw at 12:28 PM on December 5, 2012 [4 favorites]

I have learned more about Chemisty in the past 20 minutes than I have learned since 9th grade. Thanks Metafilter!
posted by Twain Device at 12:32 PM on December 5, 2012

Software Engineering, Now With Cats!

I first got a "Page cannot be found" error and thought, "This is the perfect metaphor."
posted by CancerMan at 12:37 PM on December 5, 2012 [1 favorite]

I've heard before that organic chemistry is some special kind of academic torture, but I don't understand why.

What makes it worse than Chemistry as a whole?

Every branch of chemistry is its own special kind of academic torture that cannot begin to be imagined by those who have only taken general chemistry.

It's just that organic chemistry is more likely to be taken by non-chemistry majors (especially pre-med) than other post-general-chemistry classes. Inorganic chemistry, analytical chemistry, and physical chemistry each have their own particular miseries, but those are more likely to be taken only by the chem majors (or those in very closely affiliated fields) who just hunker down and deal with it, rather than complaining about it. Or at least they only complain about it to each other rather than to the world at large.
posted by DevilsAdvocate at 12:43 PM on December 5, 2012 [5 favorites]

Now teach quantum mechanics through pictures of corgis! (Cats would be too easy.)
posted by JHarris at 12:48 PM on December 5, 2012 [3 favorites]

Argh, not even cats can make me interested in studying organic chemistry for more than like five minutes at a time.

I read the first 2.5 posts, then glazed over and just looked at the cat pictures. I'm guessing that my wife who teaches college chemistry will find this much more useful.
posted by slogger at 1:01 PM on December 5, 2012

This is brilliant.
posted by thelastcamel at 1:01 PM on December 5, 2012

Actually this is rather good. I was thinking, fleetingly, of doing this course but, well, no cats there. MOOCs and the venture capitalists who have sunk millions into you - this is where you are going wrong...
posted by Wordshore at 1:11 PM on December 5, 2012

Sweet mother of pearl, this is wonderful.
posted by you must supply a verb at 1:28 PM on December 5, 2012

I've heard before that organic chemistry is some special kind of academic torture, but I don't understand why.

What makes it worse than Chemistry as a whole?

Organic chemistry is used as a sort of litmus test for prospective med students and as a reader for the MCAT examination. (This was how my organic chemistry professor presented it to my class at the beginning of the course.) It is often taught in such a way as to intentionally feature as much rote memorization as possible specifically to test the abilities of pre-med students to rote-memorize vast mountains of context-poor information.

As a biology student who probably will not use a lot of O-chem in his life but who nevertheless could have used a solid conceptual grounding in the field (but who has no use for memorizing the literally hundreds of individual reactions and mechanisms that make up 95% of most O-chem courses and which are forgotten by everyone almost immediately after the relevant examinations) I found it frustrating, pointless, and deadly dull.

Of all the competently-taught courses I have taken, organic chemistry was the worst. Not due to the difficulty, but due to the deliberately-shitty presentation of the subject matter.
posted by Scientist at 1:44 PM on December 5, 2012 [7 favorites]

I first got a "Page cannot be found" error and thought, "This is the perfect puuurfect metaphor."

Scientist - oddly, that was my thoughts on Bio 102 - memorize Kingdom/Phylum/Class/Order/Family, be able to answer trivial differences between various taxonomies and their related evolutionary changes/adaptations. Snoozefest and not my strong point (rote).

Organic was about how to read various graphs/charts (specs, NMR, etc) to identify a molecule, naming, spatial orientation (as seen in TFA) and most importantly, synthesis/reactions (ie how to create things).
posted by k5.user at 1:52 PM on December 5, 2012

Chemistry to replace corporal punishment, says school district
posted by telstar at 1:58 PM on December 5, 2012

Hey neat! I went to grad school with James' wife. I'll see if I can convince him to come here and answer questions.

I can vouch that James is a bona fide expert in organic chemistry. His website, Mastering Organic Chemistry, has been getting tons of well-deserved attention lately. It's pretty inspiring to think he's making a successful go of it outside of the traditional academic path for research chemists.
posted by beepbeepboopboop at 2:02 PM on December 5, 2012 [2 favorites]

(He goes by @jamesashchem on Twitter.)
posted by beepbeepboopboop at 2:03 PM on December 5, 2012

Memorizing Kingdom Phylum Class Order Family is easy. "Kinky people come over for good sex". Job done.

And for me anyway there was a lot less rote memorization in my biodiversity course than organic chemistry by far. Nobody likes memorizing latin names, but at least they sound like something (which makes them easier to remember) and at least nobody expects you do to like 500 of them per course. Even my entymology course this semester, which is an upper-division course taken only by people who want to be there, only required me to memorize maybe 100 insect families. And it also had field trips and mostly involved looking at bugs under a microscope, which you can't tell me isn't a ton of fun. As for the trivial differences between various taxonomies, it helps if you think of them as important differences that both chart the history of life on Earth and also explore the weird and wonderful alternate paths that non-human lineages have taken.

Whereas O-chem was just "OK, this week we are going to do 100 slightly-different reactions involving aldehydes and ketones, here is a 35-page PDF diagramming the reactions, now we are going to go through each one step by step in PowerPoint, memorize them for the test."

My point being that it's all in the presentation. I'm sure your Bio 102 class was a dreadful slog, but it doesn't have to be if it's taught well and contextualized properly so that students are constantly in mind of the conceptual framework into which the things they are learning fit and of how awesome the tapestry is that is being gradually woven in front of them over the course of the semester. (I would argue that it's easier to do in Biology than Chemistry because so much of Biology is breathtakingly beautiful but whatevs.)

Intro bio courses can be taught badly, but usually aren't. Organic chemistry can be taught well, but usually isn't. This is specifically because pre-med students need to learn it a certain way because medical schools use it as an arbitrary litmus test and standardized tests expect pre-med students to have large numbers of reactions memorized by rote, not due to any legitimate pedagogical constraint.

What pissed me off about O-chem was not that it was a fairly dry subject that wasn't intrinsically fascinating to me, but that it was deliberately badly-taught to satisfy the arbitrary and useless requirements of bureaucratic organizations that don't even have anything to do with me.
posted by Scientist at 2:06 PM on December 5, 2012 [4 favorites]

This is specifically because pre-med students need to learn it a certain way because medical schools use it as an arbitrary litmus test and standardized tests expect pre-med students to have large numbers of reactions memorized by rote, not due to any legitimate pedagogical constraint.

This is one of the many reasons I stay the hell away from croakers.
posted by telstar at 2:13 PM on December 5, 2012

Organic chemistry is difficult if thought of as memorizing hundreds of distinct reactions, which are highly cumulative. (I believe the syllabus of the course I took stated something along the lines of "if you try to memorize all the reactions, you will fail this class"!). If seen as a system of logic, however, with a limited number of types of molecules and principles that predict their reactivity, it still requires intensive study--but ultimately becomes rewarding when all those principles coalesce, giving an intuition for how to transform a molecule from one thing to something else completely different. It actually reminds me a lot of generative syntax in linguistics, which I find beautiful for similar reasons.

I was lucky enough, however, to take the first semester of organic chemistry with a wonderful professor at a community college who, without in any way dumbing down the material, took care to teach the class in a logical, engaging, and reasonable way, and not as a weeder class. (I believe I originally got the link from my general chemistry professor at the same college, who was equally amazing!)
posted by beryllium at 2:56 PM on December 5, 2012 [7 favorites]

Quantum chemistry should be taught with giraffes or perhaps palytipi as those are some of the more improbable animals.
posted by bonehead at 2:58 PM on December 5, 2012 [1 favorite]

The content of the site is really great. He should do point groups next, but that may mean cruel and inhumane cat surgeries. Such is the price of knowledge, however.
posted by bonehead at 3:07 PM on December 5, 2012

Thanks all, for your kind comments on these cat posts. At the time I wrote this I was also thinking about writing a series of posts on how organic chemistry was like sex, but couldn't muster up the courage. I think the cat series ended up being a much cuter.
posted by james_ash at 4:50 PM on December 5, 2012 [12 favorites]

I just wanna see Krebs Cycle explained with cats.
posted by ovvl at 4:57 PM on December 5, 2012 [2 favorites]

This is really well executed, but as noted above, kind of a shallow cut. Stereochemistry is one of the few aspects of O-Chem that actually makes intuitive sense to me. It's the endless lists of reagents, reverse synthesis, spectometry and nit-effing-picky mechanisms that make it miserable IMHO. But I may be biased given that I have an O-Chem II final at 8:00 AM Monday morning.
posted by Ufez Jones at 6:44 PM on December 5, 2012

This is excellent, thanks for posting it.
posted by LobsterMitten at 6:57 PM on December 5, 2012

I was also thinking about writing a series of posts on how organic chemistry was like sex, but couldn't muster up the courage.

Muster it. Orgo as naked twister would be Teh Awesome.
posted by ChurchHatesTucker at 6:58 PM on December 5, 2012

I'm sorry, Ufez. Good luck.
posted by Scientist at 8:04 PM on December 5, 2012

Ufez, send me an email at james at masterorganicchemistry.com and I will send you something to help you for Monday.
posted by james_ash at 8:40 PM on December 5, 2012 [7 favorites]

Scientist: Weird. The order we were always taught on the memorization/math axis at my uni was Bio > Chemistry > Physics. I went with chemistry as I suck at memorization, but am not good enough at math to do physics. I really, really suck at memorization, so had a lot of trouble passing our one mandatory biochem class, as it was all route memorization, as skill I have never taken the time to develop, as it is somewhat useless.

My early orgo classes at McMaster focused on types of reactions (SN1/SN2/E1/E2), rearrangements, and then the reactivity of various functional groups. I also have a friend I'm tutoring at Waterloo who's class seems to take an identical approach. I wonder if this is a Canadian thing, or a modern thing? Either way, neither of us have spent any time memorizing named reactions, even when I took (and did quite badly on, my lowest mark ever) 3rd year Advanced Organic chemistry. That was much more 'if you have this functional group, you can do these type of reactions, etc'

james_ash: Congrats on moving to Ontario. I'm just finishing my degree and moving out west for grad school soon, but if you are in the golden horseshoe area toss me a memail, we could grab coffee or something.
posted by Canageek at 6:04 AM on December 6, 2012

I actually took organic 3 with james_ash's advisor. It was joint chemistry and biochemistry, and obviously overrun with biochemists. (I was a chemist.) He told us a lovely story about how one biochem student came to him complaining after an exam. "You expect me to understand things! How can you expect me to understand things? I'll memorise the phone book for you, but I can't understand this."

My friend the biochemist said this was a common problem -- people would take biochem, memorise everything and then flail about terribly in the last year, when you finally had enough knowledge and were expected to understand what you'd been studying.

I also took the intro to analytical chemistry with the biochemists -- it was the first year they tried integrating the groups, but the bays were assigned by program that year so I only met chemists there, too. It was a really interesting comparison. We'd have one person make a huge vat of whatever thing everyone needed, another person make a different huge vat, etc, etc, share as much work as possible and all leave as quickly as we could. The biochemists were really competitive, even in baby anal (yes, we called it that) which was not curved.
posted by jeather at 9:53 AM on December 6, 2012

Biochemistry does involve quite a bit of rote memorization, though I'd argue that it's also more relevant for the students who are typically taking it than O-chem is. Usually biochemistry is taken by pre-med students and aspiring biochemists, both of whom could use some biochemical knowledge. O-chem is only of passing relevance to anyone other than chemists and chemical engineers, who are not the main constituents of most O-chem classes.

I'm in ecology, so I guess my perspective is a bit skewed. Ecology is very much about concepts, theories, and statistics and the application of theoretical models to real-world scenarios. There's a bit of memorization, and there's a bit of math, but it's mostly about being able to synthesize theories and come up with hypotheses that explain observed phenomena. I absolutely love it for that.

Sometimes I forget that biology these days is often taken to mean molecular biology and biochemistry. That stuff is certainly important and it plays a role even in ecology (even in my lab we run a lot of PCRs for instance, and I have to be able to recognize, say, a 6-cysteine motif when I see it) but there's really a lot less rote memorization aside from nomenclature which I try to make fun by pretending that I'm a wizard and that I'm learning the True Names of all the animals so that they will talk to me. :-)
posted by Scientist at 11:57 AM on December 6, 2012 [1 favorite]

Oh, I'm not arguing that the memorization isn't relevant in biochem, or that organic 3 was more useful than memorizing all the amino acids. However, at McGill, biochem was well known to have exams that were heavy on the memorizing. Chemistry did that once, when I was there -- fill in the transition metals, which I failed terribly -- but it was a fairly memorization-free major, once you'd gotten past org 1 and learning all the chemical names. This made the chemistry classes hard on a significant fraction of the biochemists. Sometimes we'd run NMRs for them so they could correctly identify the chemical using chemical tests (it was some lab they took).

And the memorisation was in a lot of ways like arithmetic is to math, so when you got into really doing biochemistry, you needed actual understanding but if you had to be looking up each amino acid each time you did something, you couldn't possibly manage. It was foundational, but not the heart of the field.

I didn't actually know anyone majoring in biology at the time (though my friend the biochemist is now my friend the biologist, her undergrad was in biochem), so I have no particular knowledge about that major.
posted by jeather at 1:09 PM on December 6, 2012