Re: Some thoughts about undergraduate science pedagogy in classes that require retention of a large quantity of material

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There's a section in _Range_ (David Epstein; an entertaining book) that supports everything you're saying in the post. I'll see if I can find an excerpt. . .


Posted by: NickS | Link to this comment | 03-29-20 7:51 AM
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I can't find the exact passage, but this is a related section from the same chapter.

https://books.google.com/books?id=1ZyaDwAAQBAJ&pg=PA85&lpg=PA85&dq=One+of+those+desirable+difficulties+is+known+as+the+"generation+effect."+Struggling+to+generate+an+answer+on+your+own,+even+a+wrong+one,+enhances+subsequent+learning&source=bl&ots=dh8dQ_9Sin&sig=ACfU3U00iTpaot1sBF45RP0hjCHZCXCT8A&hl=en&sa=X&ved=2ahUKEwj737qJ-7_oAhUHG80KHTkJAYYQ6AEwAnoECAEQAQ#v=onepage&q=One of those desirable difficulties is known as the "generation effect." Struggling to generate an answer on your own%2C even a wrong one%2C enhances subsequent learning&f=false


Posted by: NickS | Link to this comment | 03-29-20 8:05 AM
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I guess, thinking about my own class the one time I taught, my own post suggests a better approach than the one I took. I assigned reading and had a quiz in class every week to try to enforce doing the reading. When it became clear that my students didn't really know how to engage with the reading I gave them study questions, but some of them "looked at them" and didn't bother to write the answers down. What I probably should have done instead of a stressful in class quiz was study questions, the answers to which they had to post to Blackboard, and a take home online quiz. Although they all would have just collaborated is the problem with the latter part of that.


Posted by: Tia | Link to this comment | 03-29-20 8:07 AM
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2: Even that's related. Part of what I'm complaining about is drilling to the point of overconfidence. It's not a good use of study time and doesn't encourage accurate self-knowledge about the true degree of your mastery. Stop when it seems like I've mostly got it and catch me again in one or two days.


Posted by: Tia | Link to this comment | 03-29-20 8:15 AM
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Oh I've never heard of Anki flashcards and looking at it it looks super useful for learning languages. I usually make my own flashcards and carry them around but have gotten too lazy in my old age to make them any longer.


Posted by: Barry Freed | Link to this comment | 03-29-20 8:20 AM
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Are we just going to assume that molecules are real?


Posted by: Moby Hick | Link to this comment | 03-29-20 8:21 AM
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Page 88

IF that eighth-grade classroom followed a typical academic plan over the course of the year, it is precisely the opposite of what science recommends for durable learning -- one topic was probably confined to one week and another the next. Like a lot of professional development efforts, each particular concept gets a short period of intense focus, and then on to the next thing, never to return. That structure makes intuitive sense, but it forgoes another desirable difficulty: "spacing" or distributed practice.

It is what it sounds like -- leaving time between practice sessions for the same material. You might call it deliberate not-practicing between bouts of deliberate practice. "There's a limit to how long you should wait," Kornell told me, "but it's longer than people think. It could be anything, studying foreign vocabulary or learning how to fly a plane, the harder it is, the more you learn." Space between practices creates the hardness that enhances learning. One study separated Spanish vocabulary learners into two groups -- a group that learned the vocab and then was tested on it the same day, and a second that learned the vocab and was tested on it a month later. Eight years later, with no studying in the interim, the latter group retained 250 percent more. For a given amount of Spanish study, spacing made learning more productive by making it easy to make it hard.

Posted by: NickS | Link to this comment | 03-29-20 8:28 AM
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I decided not to assume that Anki couldn't do what I want.


Posted by: Tia | Link to this comment | 03-29-20 8:32 AM
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Part of what I'm complaining about is drilling to the point of overconfidence

There is also a section on that specific idea, but it's longer than I want to re-type (and half of it isn't available on the google books summary), but I'd recommend looking up that chapter -- does your library let you check out e-books? -- it's short, very readable, and matches up quite well with your OP.


Posted by: NickS | Link to this comment | 03-29-20 8:32 AM
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You might call it deliberate not-practicing between bouts of deliberate practice.

That explains my good grades in Spanish, but not why I can't play the clarinet.


Posted by: Moby Hick | Link to this comment | 03-29-20 8:32 AM
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9: I think so and also I think one can only recently apply for a library card online. I had one a long time ago but I dunno its status.


Posted by: Tia | Link to this comment | 03-29-20 8:45 AM
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I don't know anything about this, maybe having failed to ever learn anything since I memorized the multiplication tables, but isn't this kind of class not designed for pedagogical purposes at all? Isn't the function almost entirely to weed?


Posted by: peep | Link to this comment | 03-29-20 9:00 AM
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12: It's both. My professor definitely sincerely cares that we learn the content, has tried to encourage us to become chemists rather than doctors in study sessions, put up slides of women scientists and talked about them on the class before Women's Day, etc. I mean, you can always write a test that will weed, but why not have everyone learn more rather than less while their dreams are getting crushed?


Posted by: Tia | Link to this comment | 03-29-20 9:05 AM
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She's also expressed distress that we're below the national average for the ACS exam. She doesn't have it in her power to rewrite the online textbook but she does have it in her power at least to create smaller discrete chunks of interspersed material at every homework due date out of the problems provided.


Posted by: Tia | Link to this comment | 03-29-20 9:09 AM
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but why not have everyone learn more rather than less while their dreams are getting crushed?
Mouseover.


Posted by: Mossy Character | Link to this comment | 03-29-20 9:10 AM
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Some math textbooks have older material interspersed with newer material. But the best math courses are the ones where you don't need to review old material because you are using it in the material that follows. The worst ones are Precalculus and algebra where every single chapter is standalone, and the choices were made 50 years ago, and in the elapsed time some weird peacock evolution took place towards increasingly complicated mating dances of dumb tricks and hoops to jump through. C/f rational zeros theorem in a math-for-poets class.


Posted by: heebie-geebie | Link to this comment | 03-29-20 9:59 AM
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How come they don't make a poetry-for-mathematicians class so the math majors don't need to learn the hard poems?


Posted by: Moby Hick | Link to this comment | 03-29-20 10:01 AM
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You should get some course with every poem starting with "Roses are red" or "There once was a man from Nantucket."


Posted by: Moby Hick | Link to this comment | 03-29-20 10:05 AM
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There once was a man from Nantucket,
He for God only, she for God in him,
Burma-shave.


Posted by: lourdes kayak | Link to this comment | 03-29-20 10:13 AM
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5: M/tch found them useful for learning Spanish. https://blog.fluent-forever.com/spaced-repetition/


Posted by: Sir Kraab | Link to this comment | 03-29-20 10:14 AM
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" as annoying as it is to draw molecules by clicking on little lines and C's and H's and O's"
I am totally up for teaching you SMILES if you want (and if the drawing program you're using accepts that as input.)


Posted by: SP | Link to this comment | 03-29-20 10:24 AM
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There once was a man from Nantucket,
Studying algebra from a course kit.
He said with a grin
As he scratched on his chin,
Let's write "x=6" and then fuck it.


Posted by: Moby Hick | Link to this comment | 03-29-20 10:47 AM
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21: That's so nice of you, but I'm pretty sure there's no way for this program to take any text input. You just have to use its drawing software.


Posted by: Tia | Link to this comment | 03-29-20 10:50 AM
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Try copying pasting (crtl-C ctrl-V) C1CCCCC1 into the software and see if anything happens.


Posted by: SP | Link to this comment | 03-29-20 11:12 AM
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Nothing happened. There's really nothing resembling an input field that could accept text. (There's a watermark behind the input box that says MarvinJS by ChemAxon, if that sounds familiar.)


Posted by: Tia | Link to this comment | 03-29-20 11:21 AM
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Oh but hm. If I right click on a drawing element (though not the canvas) I get some option to past "attached data". Interesting.


Posted by: Tia | Link to this comment | 03-29-20 11:24 AM
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Yeah Marvin is the most commonly used web app drawing tool, eg ebi.ac.uk/chembl then click draw structure at the top right and you should get a similar interface. Maybe the paste option can be disabled by the instructor.
Anyway I don't mean to distract you by learning something else but it is a fairly simple way to avoid lots of clicking once you've picked up the basics.


Posted by: SP | Link to this comment | 03-29-20 11:40 AM
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Gosh, I'm not quite sure what to say, other than the books I taught and learned out of seem pretty different than yours. It is hard to teach cumulative topics, introducing new material while aggressively referencing prior work during lectures, but we/I always emphasized learning the patterns. By the end of the course, the top 20-30% of students could usually guess the first couple steps of new material based on understanding patterns (because we'd beaten if into their skulls? yep).

I think, realistically, there is a lot of rote learning in science at the beginning of any topic, just like there's a lot of rote leaning when you start learning a language. Learning an alphabet, vocabulary, how to conjugate verbs - you start there, then move to more complex conversation and reading passages. I guess you can learn by immersion, too, not sure how the learning process works there.


Posted by: ydnew | Link to this comment | 03-29-20 2:35 PM
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If you are learning organic chemistry by immersion, don't start with benzene.


Posted by: Moby Hick | Link to this comment | 03-29-20 2:48 PM
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29: Ethanol. Methanol is also deprecated.


Posted by: | Link to this comment | 03-29-20 2:49 PM
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I learned orgo at one school and taught intro at another and think the latter was quite inferior despite the professor being very popular. His method involved memorizing reactions that are totally disconnected from chemistry as actually practiced- even when the mechanism was common to other reactions (eg this is an oxidation, this is a reverse Aldol) he didn't teach that but rather just focused on what changes about the molecules in the reaction. So you had to memorize all these steps and reaction names and substrate atom patterns and use them to solve problems you were given (what reactions would you use to break this molecule into these three parts?). When I learned orgo we had electron pushing drilled into our heads- this is how you draw the arrows, and don't skip steps even if you get the right answer because you need to show that you understand those rules. I understand the goal of teaching people to think about organic as a series of reactions to do what you want, but the focus on mechanism was way more useful later on. In my opinion it's also much easier to learn, but maybe that's just my learning style where I prefer rules vs memorizing facts- memorization seemed to be much preferred by the premeds. The material I had the hardest time with in another class was memorizing all the amino acid one letter abbreviations.


Posted by: SP | Link to this comment | 03-29-20 2:55 PM
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Wait, I want to be fair. It's not like there's no effort to refer back to earlier concepts, either by the professor or the book. There is. If I'm giving the impression that there's not, that's wrong. But by the time I've answered my 20th question in a relatively short span that establishes that I understand that deactivating groups on benzene rings are meta directors, or whatever, I'm like, why did I do this twenty times? I understood. In fact, it offers an illusion of mastery by giving me versions of the same problem that I know how to do over and over when I may well not remember something about it that I really need to soon enough. It is way more of a problem that I am forgetting how to do something I could do fluidly even two weeks ago than that I'm struggling to initially learn the topic and need intensive drill on the first pass. This doesn't seem like the right allocation of time to me. And given that the homework is already computerized it wouldn't be that hard to make it adaptive, like Anki.


Posted by: Tia | Link to this comment | 03-29-20 3:08 PM
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That was to 28. I also don't want to give the impression that we aren't encouraged to learn mechanisms. *Right now* I could draw you a mechanism that explains why deactivating groups are meta directors. I just need to be asked to do that on the regular if I'm going to remember how to do that, along with eleventy bajillion other things, on an extremely time-pressured test.


Posted by: Tia | Link to this comment | 03-29-20 3:13 PM
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"Deactivating groups on benzene rings are meta directors"
Ooh ooh- ok- so do they explain mechanistically why that is, or do you just have to memorize it as a fact and if you're told to do an electrophilic aromatic substitution on benzylic acid you just are expected to say where the addition happens without showing why?


Posted by: SP | Link to this comment | 03-29-20 3:15 PM
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That has to be the most specific pwn in the history of the blog.


Posted by: SP | Link to this comment | 03-29-20 3:16 PM
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34 see 33!


Posted by: Tia | Link to this comment | 03-29-20 3:16 PM
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The pwner becomes the pwned.


Posted by: Tia | Link to this comment | 03-29-20 3:24 PM
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My goodness, this is an unexpectedly DELIGHTFUL conversation to see on Unfogged. I'd say in both universities where I learned and taught, it was a mix of mechanisms and synthesis. My grad school classmates came from different traditions, and we'd debate which approach was best. One guy was always on the side of no memorization. I was not. You've got to memorize reagents in order to do synthesis problems; unless you're way smarter than I am, it's nearly impossible to just work out that, eg, CrO3 is going to oxidize secondary alcohols to ketones. I mean, you could, I suppose. The crazy thing I found students doing was memorizing one example of that kind of reaction and not generalizing it to ALL secondary alcohols regardless of the rest of the structure (yeah, there are exceptions and all, but generalizing is OK for undergrad premeds). That said, you should basically never need to memorize a mechanism other than general rules of how things react (acids protonate stuff first. Bases deprotonate stuff first. Nucleophiles attack electrophiles).

So, in this system, you learn a new reaction. You have a functional group transformation and a mechanism. The functional group transformation should probably just be memorized, however it works fo pr a given student (I have opinions!), and the mechanism should be walked through in class by asking what should ALWAYS happen first when you have a base/acid/nucleophile/whatever and continue like that.

Then, for homework, there should be a few easy problems (A reacts with B to make what? or what reagent do you use to go from A to C?), a few mechanism problems, and a few synthesis problems where you need the prior functional group transformations to make a more complicated product.

Quizzes should be mostly something low-key, one quick question to make sure most people got the basic concept taught the class before to see whether folks are falling behind or whether you fucked up your lecture that day.


Posted by: ydnew | Link to this comment | 03-29-20 3:32 PM
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I don't know how far this has spread, but at Tia U there are "clickers" -- challenging, timed (75 seconds or so), graded quiz questions -- at random intervals throughout lecture. It's stressful. Sometimes those clickers are a means of review, but it feels especially startling to be suddenly asked how well you remember the last chapter in that format, instead of in homework when you could have some time to think.


Posted by: Tia | Link to this comment | 03-29-20 3:38 PM
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Is there like a bell to call you to the quiz?


Posted by: Moby Hick | Link to this comment | 03-29-20 3:45 PM
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Yes, and sensors to track your salivation, otherwise known as "learning analytics."


Posted by: lourdes kayak | Link to this comment | 03-29-20 3:48 PM
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Oh yeah, the classrooms were capable of that back when I taught, but no one did it. Generally, course grading was something like 60% from your best two of three exams, 30% from your final exam, and 10% from the little in class quizzes or homework assignments.


Posted by: ydnew | Link to this comment | 03-29-20 3:49 PM
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you should basically never need to memorize a mechanism

I don't know; if you know you might have to reproduce something quickly on a test you need it -- maybe not memorized exactly, but rehearsed. *Right now* I can visualize where which Cl in that Cl-Cl-AlCl3 complex gets the positive charge, and which the benzine ring attacks, but in three weeks? No. And it won't be because I don't understand that pi bonds are nucleophiles that attack electrophiles.


Posted by: Tia | Link to this comment | 03-29-20 3:52 PM
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I'm picturing a button that the professor hits and everybody hears, "Bueller? Bueller? Bueller?"


Posted by: Moby Hick | Link to this comment | 03-29-20 3:54 PM
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43: Everyone has stuff that will work better or worse for them to learn, but I'd say if I were grading that mechanism, it would be a high value question, let's say 20 points. For a full score, you'd need to make the complex correctly and attack the correct Cl. BUT, that might be 3 points out of 20 for the question. If you just wrote "Cl+" being attacked by the pi bond and got the rest of it right, you'd probably get 17/20, because you showed you understood the important parts, not the unusual, hard to work out from first principles, bit of the question.

It was always really important to us to assign partial credit for everything the students could show us they knew. As a student, it's really easy to get stuck on something like that and spend lots of time on it without moving on to what you do know. We encouraged students to give us even the first or last step of something so we could give partial credit. Our rule for multistep syntheses was partial credit for any correct reaction, whether it was on the correct path to the product or not. It was hard for them to remember under pressure, but we tried really hard to grade in a way that they did get credit for what they could do.

That said, if your class isn't run like that, it sucks, and yeah, you can do a lot of practice to make sure all those details come automatically to you, but it's laziness on the part of the prof/lecturer/grader if they're emphasizing things like that, even in a class meant to be a gatekeeper.


Posted by: | Link to this comment | 03-29-20 4:12 PM
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45: It's just possible that something like that would come up on a multiple choice question and be all or nothing, and a bunch of mistakes like that add up to a lot of lost points. I know you said earlier you always used partial credit even on multiple choice but that isn't the practice in this class. The attitude is: you really should know it. But "it" encompasses a lot of stuff. The professor actually explicitly said, in going over some commonly missed multiple choice questions, that these were points students missed that there was no reason to miss. (Because we should know it.)

Anyway, even if the grading in the class were more sensitive, I would still think more organized spaced repetition of material we're expected to carry through to the final (and eventually the MCATs) would aid retention for everyone. It's just a well-established principle of learning. It's not that there's no repetition or carry through, but it's not enough and it's not orderly enough. I know I can do it for myself and will next time through, but it's frustrating that I'm going to have to individually make up a bunch of tools that could be more efficiently handled by some centralized somebody.

An individual somebody did something like it for the MCAT. Probably there's an organic chemistry tag; I should check it out. I'd just like a solution that includes spaced repetition of problems, not just facts.


Posted by: Tia | Link to this comment | 03-29-20 4:34 PM
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46: It sounds like your class isn't a very good one, unfortunately. Tutoring offer still stands, and when you retake it, you might want to look hard at your professor/lecturer options. Unless the grading and exams are standardized across sections, you might do better with someone else. Did I mention that often summer classes are a good option for people who just need to get through? It's like bootcamp in some ways and awful for longterm retention, but the courses move so fast that the curve is usually generous, and we often saw higher grades over summer than during normal semesters. It's also the only thing you do for a month straight, so it's a bit easier to focus, or at least that's what the students told me.

And yes, I bet there are tons of resources out there for organic chemistry, particularly because it's the part of the MCAT premeds tend to dread the most. I taught MCAT prep once as a volunteer (semi-volunteer? I think I got paid $50 or something). It was fun but weird.


Posted by: ydnew | Link to this comment | 03-29-20 5:24 PM
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"memorizing one example of that kind of reaction and not generalizing it to ALL secondary alcohols"
Oh god this. Multiple students. They wanted to know how they could be expected to learn the answers if there were infinite possible variations and I'm like that's why it's cool!


Posted by: SP | Link to this comment | 03-29-20 5:38 PM
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47: I just checked out registering for the summer session. It won't let me do it right now because I'm in the same class. I'll try calling the school and asking whether officially withdrawing affects my access to class materials; I have till like mid May to do it now. Then I will take some of that tutoring!


Posted by: Tia | Link to this comment | 03-29-20 5:47 PM
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Maybe relevant, I found this web page/essay/thing about quantum computing to be pedagogically interesting. Kind of book-like but with some built-in spaced repetition testing.


Posted by: Nathan Williams | Link to this comment | 03-29-20 6:55 PM
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We start online classes tomorrow, and I'm nervous I'm somehow going to be "doing it wrong" despite my chairs saying that any good faith effort to teach in these circumstances is sufficient.


Posted by: J, Robot | Link to this comment | 03-29-20 7:26 PM
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I hear your concerns. I also heard Neil Diamond, but he felt I wasn't listening either.


Posted by: Opinionated Chair | Link to this comment | 03-29-20 7:36 PM
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51: We do too.

I'm insanely nervous because I make so many typos - both written and verbal - when I write math. In class, usually someone catches it, or I notice someone has a funny look on their face, and I clarify, and it doesn't seem to matter very much. But if they're scrutinizing my practice test answers as they're studying for a test, in isolation, and there's an error in there, it could really mislead them. And the process of setting them straight would be really difficult to ensure that everyone knew what was being clarified, and where, etc.

I've been proofreading my work, and the errors are so dumb - like, I just stopped halfway through an answer and went on to something else. Or used the wrong equation. Or whatever. Any of those could really be deadly if they'd slipped through. Aaaaugh.


Posted by: heebie-geebie | Link to this comment | 03-29-20 9:52 PM
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50: That looks cool, and I'm interested in learning more about quantum computing. I started reading/registered.

Someone on the Anki subreddit pointed out that there's an add-on, Syllabus, that lets you see your retention rates for all decks, sub-decks and tags in a single view, and you could pick a deck to study based on lowest retention rate. It's crude compared to the thing I want, which is getting algorithmically and automatically served a sample from a group if I need to review it that day, but it is something.

I poked around and learned that Anki is written in Python and has friendly documentation to orient you to the project; I could scarcely find something easier for me to write for, so at some point I might consider just trying to build the thing that I want.


Posted by: | Link to this comment | 03-30-20 5:59 AM
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ZOMG I had the best of both worlds idea. I wanted to offer to help my quasi romantic partner financially because though I don't know this for sure since it seems not my business I don't think his immigration status can possibly be quite regular and he is fucked for work right now. But better than a gift is getting paid for legit work you did, and I can have him make this goddamned Anki deck. He even used to be an organic chemistry TA, so he'll be able to make intelligent tags. And he even knows how to program although probably less well than I do so I'm not sure I can set him loose making an Anki add on but we could maybe work on it together. Anyway I just told him I would pay him to do something at home on line and he was into it.


Posted by: Tia | Link to this comment | 03-30-20 11:17 AM
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55: smart


Posted by: soup biscuit | Link to this comment | 03-30-20 11:24 AM
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Anyway I just told him I would pay him to do something at home on line and he was into it.

He's going to answer the zoom naked.


Posted by: Moby Hick | Link to this comment | 03-30-20 11:29 AM
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I'm starting to feel panicky about working from home. I woke up at like 5 to get a bunch of shit done before the kids woke up. Jammies went to our makeshift office at 8 and I did the kids' school until lunchtime. Fine.

Now it's the prearranged time for me to work, but Jammies is, of course, teaching live in our little makeshift home office and I'm terrible at concentrating with any sort of background noise. A bunch of work emails are flying and require concentration, and I don't even know how I'm ever going to keep up. Let alone stay on top of my classes.


Posted by: heebie-geebie | Link to this comment | 03-30-20 11:35 AM
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Headphones and brown noise for situations where you're not on a call!


Posted by: Tia | Link to this comment | 03-30-20 11:37 AM
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heebie, RainyMood.com and basic headphones work for me. My household is now up to four adults and an 8-month old, since we took in family from NYC.


Posted by: Witt | Link to this comment | 03-30-20 11:44 AM
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We're not so crowded, but it turns out that teenagers can be really surly.


Posted by: Moby Hick | Link to this comment | 03-30-20 11:47 AM
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The noise-cancellation headphones weren't enough when Jammies and I were sharing a little table. But now I'm in our bedroom on a TV tray and the headphones are enough. Although the kids seem to be disintegrating now.


Posted by: heebie-geebie | Link to this comment | 03-30-20 11:52 AM
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Also I opened up my work laptop just now for the first time since March 12th, and it was open to the Johns Hopkins map, showing the US total cases at 5K. Unreal.


Posted by: heebie-geebie | Link to this comment | 03-30-20 12:00 PM
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Sorry all, just feeling a bit fragile. Meltdown over.

I think I'm upset that this fucking quarantine is turning out to be so over-scheduled and stressful, global crisis aside. These teachers are heroes, I'll readily admit, but I don't really care if the children of our future marinate in their juices for a month or two instead of learning all the things.

Actually:
Pokey and I watched his teacher go over the forty different avenues for learning this morning, and then he totally lost his shit, "How do I know where to start? Which things are due and which things are just extra? When is anything due? How do I turn stuff in?" Like his wild-eyed "I'm not okay" panic. Then about ten minutes later, his meds kicked in and he was like, "You know what? I'll start with the things I like, and then find out more at the zoom session this morning."

It is possible that the same applies to me and I should just give my own meds another ten minutes to kick in.

This has been Interior Monologues With Heebie, thank you for tuning in.


Posted by: heebie-geebie | Link to this comment | 03-30-20 12:06 PM
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Sorry all, just feeling a bit fragile.

I've had that feeling despite being in a fairly good situation (no kids, stable work, financially secure . . . ) I still feel like I'm just tied and stressed all the time. Working from home is a hassle, and adds to my stress but it's mostly the feeling of everything seeming unsettled, uncertain, and depressing.


Posted by: NickS | Link to this comment | 03-30-20 1:04 PM
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ZOMG. I know no one here but ydneW has my current level of investment in organic chemistry pedagogy but I need to complain about something.

I'm going through this book Organic Chemistry as a Second Language as a way to review first semester topics and get ready for trying second semester again. It's by the same author as my textbook, but it's meant to be independent.

In the introduction, arguing against memorization, he says:
____
You probably know at least one person who has seen one movie more than five times and can quote every line by heart. How can this person do that? It's not because he or she tried to memorize the movie. The first time you watch a movie, you learn the plot. After the second time, you understand why individual scenes are necessary to develop the plot. After the third time, you understand why the dialogue was necessary to develop each scene. After the fourth time, you are quoting many of the lines by heart. Never at any time did you make an effort to memorize the lines. You know them because they make sense in the grand scheme of the plot. If I were to give you a screenplay for a movie and ask you to memorize as much as you can in 10 hours, you would probably not get very far into it. If, instead, I put you in a room for 10 hours and played the same movie over again five times, you would know most of the movie by heart, without even trying. You would know everyone's names, the order of the scenes, much of the dialogue, and so on.

____

Uh, has this person ever tried to learn lines to do a scene or a play? You absolutely sit down and try to memorize. You don't just watch or read something over and over.

Anyway, at the end of the chapter I'm working on now, he says:

____
Students often try to memorize the stereochemical and regiochemical outcomes of every single reaction. This method of studying will prove to be very difficult as you move through the course, because there are many, many reactions. It is not easy to memorize all of the details. However, if you focus on understanding the proposed mechanism for each reaction, with a complete understanding of how the mechanism justifies both the stereochemical and regiochemical outcomes, then you will find that you will remember the details of each reaction more easily (without much need for memoriza- tion). Each mechanism will make sense, and that will help you remember all of the details for each reaction. This is true because a mechanism must explain all of the experimental observations.

For each mechanism that you encounter, you should be able to draw the entire mechanism on a blank piece of paper. Make sure to do that for every new mechanism. Then, wait a day, and do it again, when it is not fresh in your mind. For each mechanism that you learn, you need to get to a point where you can draw the entire mechanism, without mistakes, on a blank sheet of paper. If you discipline yourself to perform this exercise, you will find that your understanding of organic chemistry will be greatly enhanced (as will your grade in the course!). Good luck!
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THIS IS MEMORIZATION. In fact, it's memorization based on drill through spaced practice, which I was arguing for in the main post. Maybe make your text enforce this if you think it's a good idea! It's just memorization of a few core examples from which you need to be able to generalize. I dunno, it feels like people are so set on emphasizing that more than memorization is necessary, that you also need understanding and pattern recognition, that they don't understand when they themselves believe that memorization is necessary.


Posted by: Tia | Link to this comment | 05-22-20 11:15 AM
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I think he's arguing against the robotic unthinking memorization that I believe was mentioned upthread (it's been like 15 years since we discussed this, right?) That's where people memorize m-chlorobenzaldehyde does this and then when they have m-fluoro or it's m-chloro but part of a larger molecule they have no idea what to do. Of course you need to remember that an Sn2 reaction involves a certain substitution occurring at the reactive center and only works with certain groups at that location, but if you remember that instead of memorizing every Sn2 reaction you've ever seen you'll get a lot farther.
The part that turned me off in more advanced organic chemistry was the requirement to memorize named reactions. That is straight up senseless memorization that obviously has no logic to it, maybe aside from a few cases where you might know that so and so worked with so and so and therefore the reaction is a derivative of the advisor's reaction.


Posted by: SP | Link to this comment | 05-22-20 11:32 AM
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I know but he is arguing for it muddily and poorly! What he needs to say is that you need to be discerning about when you need to memorize and when you need to generalize from a pattern you have memorized. A very helpful textbook might even label the points it would be smart to have memorized. Honestly, memorizing every reaction mechanism presented in his textbook is a lot of memorization in and of itself. And since he himself understands that it's possible to forget reaction mechanisms even when you understood them the first time, why not help the student and make sure that the questions that rehash older mechanisms are sprinkled throughout the text. Why not make electronic homework intermittently space practice of different concepts? Why not make it adaptive to what the student actually needs to practice?


Posted by: Tia | Link to this comment | 05-22-20 11:47 AM
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Sure, I agree with that. At some point it's less memorization of rules and more memorization of principles- if you look at molecules, what are the reactive groups, electrophiles, nucleophiles, hard, soft, hindered, etc. and you have to figure out what's likely to occur. He should get people to start thinking about that by pointing out those principles within the mechanisms you have to learn.
My undergrad research advisor, who I didn't know very well since I was a crappy undergrad researcher, died of COVID last week. He was in his 80s and had dementia and I assume was in an affected nursing home. He's known for writing one of the more famous intro organic textbooks but doesn't sound like the one you're using.


Posted by: SP | Link to this comment | 05-22-20 2:33 PM
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Again from this book: All of the relevant information is summarized in the following flow chart. It is important to know this flow chart extremely well, but be careful not to memorize it. It is more important to "understand" the reasons for all of these outcomes. A proper understanding will prove to be far more useful on an exam than simply memorizing a set of rules.

No. You can memorize something and understand it, and particularly when you are brand new to a subject, when you can be at the stage of understanding something but not yet finding it second nature, you will be faster at retrieval on an exam if you have that chart memorized than if you have to carefully reason from first principles on every problem. I feel like he doesn't understand that there are degrees of understanding -- there's "hm, yes, that makes sense" and there's "I understand this so well that nearly automatically I can apply these principles to every new situation" and many in between, and students will probably move through some of those stages for different subtopics while they progress through the course, and different strategies might be necessary the first time you are tested on a subtopic and the third. Or maybe he understands at a shallower level but isn't able to demonstrate his understanding at the level where it shows in every sentence he writes!

And what is with these quotation marks for emphasis? Am I reading the sidewalk chalk stand outside a juice bar?

I dunno, I just get mad because I think in this guy's zeal to correct overreliance on memorization he has lost some empathy with what it is like to be a beginner at this subject and is giving bad advice. I even like this book, and my textbook, but being constantly told I shouldn't have to do something to study in order to do well, especially by someone who is advocating that I do it in other places, is aggravating.

Sometimes I don't feel like people who are very facile with a subject are always the best people to teach it. I remember when I had just dropped out of grad school and I was exploring making money tutoring I was chatting with a friend and said I thought I might be better at tutoring math for standardized tests than English -- I had learned the rules that governed high performance on the English sections so long ago and they were so deeply ingrained as to be nearly invisible to me, and I didn't really understand the steps on the way to doing better. This guy is obviously interested in scaffolding as a concept but is actively misleading about some elements of it.

This also reminds me of the time I made the mistake of going to my orgo 1 professor's office hours and he started quizzing me (on the material in this same chart), and because I was a little slow and startled by it, he said something like, "oh, you don't know this" (I did know it! And could have reproduced this chart from memory), because he did not understand the difference between not knowing something and not being able to retrieve it as quickly as an expert.

Gah!


Posted by: Tia | Link to this comment | 05-23-20 5:59 AM
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My professor in the second class is decrying the discouragement of memorization in orgo, and across fields. I'm so happy.


Posted by: Tia | Link to this comment | 05-27-20 7:01 AM
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