Monday, April 18, 2016

A lot of people have strong feelings about organic chemistry education

Also from this week's C&EN, a couple of really interesting letters about 'the youths' and organic chemistry, using Bethany Halford's article about a recent ACS San Diego symposium as a starting point:
“Overwhelmed by Orgo” (C&EN, March 28, page 24) on the crisis in organic chemistry education struck a chord. As an organic chemistry instructor at the university level for more than 20 years, I can attest to a noticeably diminished student capacity to handle the subject with each passing semester. 
It should be emphasized, however, that organic chemistry is not and was never intended to be an easy discipline to master. Hand-wringing over new teaching techniques or providing yet another clone of the texts is an exercise in futility. Jazzing up texts with pictures and graphics does little more than inflate already obscene prices. 
My suggestions to include at least a rudimentary introduction to organic chemistry in the preparatory general chemistry curricula have been met universally with stiff resistance. As a result, students are thrown into the deep end with no swimming lessons. 
But the core problem is endemic to science education in general. Students go unchallenged through their first 12 years of formal education, rewarded exclusively by rote memorization with no opportunity to develop skills in critical thinking and problem solving by analogy, essential elements of organic chemistry. Disturbingly, many of those considered successful at the university level are so only because rote memorization is now embraced by their professors as well. 
Robert G. Davis
Naugatuck, Conn. 
In C&EN’s article, Melanie Cooper, a chemistry education professor at Michigan State University, states, “Students come out of general chemistry typically very unprepared.” Worse, I’ve found, they graduate college very unprepared. 
I routinely give a 12-question chemistry quiz to interviewees/applicants looking for employment as a bench chemist. I have found that they and even some recent hires are poorly prepared for jobs in chemistry. For instance, they cannot explain the difference between a weak acid and a dilute acid or the difference between an end point and an equivalence point. 
One interviewee, prior to taking my short chemistry quiz, told me he tutored chemistry, but he only got 6.5 correct answers out of 12. And a recent graduate with a B.A. in chemistry whom I had hired, and who has thankfully left, didn’t know that mercury was a liquid. 
Who lets these people graduate high school or college? Educators should be held liable for poorly educating students. Some teachers are “teaching-disabled.” If you really want to improve the quality of chemistry students going into the working world, put pressure on the secondary schools and colleges to stop graduating those who simply put in four years. The education and work ethic are not there. 
Fred G. Schreiber
Newark, N.J.
Regarding the first letter, I actually deeply agree that organic chemistry is just a difficult subject, and there's not a lot that people can do to change that fact. 

Regarding the second letter, there's a certain "kids these days/teachers these days" vibe to it. At the same time, I think it's important to note that we all have something I'm going to call "intelligence-essential facts" - that is "if you don't know this, you're stupid about this subject." For Dr. Schreiber, it is (apparently) "what state of matter is mercury?" (For what it is worth, if I think that if you spend 4 years in a chemistry program and you don't realize that mercury is a liquid, true, there has been a hole in your education somewhere.)

I am not sure what my "intelligence-essential facts" are, but I am sure that I have them. It'd be interesting to get a copy of Dr. Schreiber's 12-question quiz to see what he considers important. 

36 comments:

  1. One thing driving the "kids-these-days" stuff is that undergrad chemistry programs spend less time on the fundamentals to make room for newer instrumental techniques. All that time spent talking about NMR, GC-MS, etc means that new graduates are lost if they end up at a smaller company relying on old-school wet-chemical analytical techniques, and their older co-workers are thinking "why didn't he/she learn this stuff in freshman chemistry?"

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    1. I see some "top" chemistry programs who skip Quantitative Analysis altogether. Whatever happened to requiring three semesters of calc plus diffy q?

      Everyone is looking for shortcuts, I guess.

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    2. My undergraduate department didn't require it, and that was 20-25 years ago.

      We didn't really have much in the way of analytical chemistry (and not much polymer chem) which wasn't great. Everyone had to take two semesters of calc, and most people took differential equations, but I don't know if it was required. From people I knew in grad school, we had less lab and less analytical than other schools.

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    3. My undergraduate program at an Ivy also doesn't teach analytical or polymer chem. Too blue collar.

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  2. One problem at the secondary level is "No child Left Behind", where teachers are required basically to pass all students to the next level. To so, many teach to the slowest learner, so education is forced by law to dumb down.

    I taught Org, and its a very difficult subject to teach in an interesting way. If find to get students attention in General Chem demo's work but that going to be a little tricky and dangerous with Organic Chemicals. Another problem is that students these days are expected to have a gazillion outside activities and interests to get into professional schools so they really don't have the time to study Org, or anything else, like they should.

    On top of all that is grade inflation due, in part, to student evaluations of teachers that are now on the internet. I recently breathed a huge sigh of relief at the sight of my my first "Rate my Professor" score from a student put me at Green code. I do give a lot of A's.

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    1. Is this "teachers are required basically to pass all students to the next level" actually true?

      If the data in http://www.ajeforum.com/could-the-common-core-state-standards-affect-high-school-graduation-rates-by-kelly-griffith-and-victor-sensenig/ are to be believed, it does look that NCLB did foment an increase in high school graduation rate, but just back to where it was in the early 70s (back when students were smarter and worked harder---damn hippies, who now run the country!), and at a rate similar to American industrialization post depression.

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    2. I have seen people argue that you should give as many A's as possible to get better evaluations, which can affect tenure and salary increases. This would contribute to people graduating who do not know as much as expected, and perhaps setting the bar too low for a sense of mastery.

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  3. When it comes to "intelligence-essential facts" - my dentist talked me into buying this snake oil the other day:
    https://www.dentalherb.com/tooth-and-gums-tonic.html
    I was furious when I got home and saw "Made Without Chemicals" on the label. I probably would have loudly demanded to know whether he passed undergrad chemistry if I had noticed this when I was still in his office!

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  4. To be fair, Hg does solidify around -40, so perhaps this person was referring to experience in February in Whitehorse?

    Doesn't every generation think the younger generation are lazy and stupid? Why, in my day we didn't use lab clamps to hold our flasks for refluxing toluene, we stood there and held over the bunsen burner with our hands, and we'd stand there for hours and hours if neccassary, even in snow storms at night! That was the way it was, and we liked it.

    To be fair, when I read about 'trigger words', 'safe spaces', banning dodge ball, and stuff like this http://www.theatlantic.com/politics/archive/2015/12/the-food-fight-at-oberlin-college/421401/ I do start to think maybe millenials are a little soft, though none of them I've actually worked with has been so.

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    1. I was thinking mercury has been deemed so toxic/dangerous that I doubt any undergrads actually get to experience it in person. I was lucky to have a drop to play with (even in a tube) that was quite instructive as a high density liquid.

      If you want to see the weakness of this generation in action look at a Milo Yiannopolous video on youtube. College students thrown into hysterics at the idea someone disagrees with them.

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    2. Anecdotal evidence is my favorite evidence.

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  5. I fear that these letter writers would be shocked to find that it is they and the field, not the students, who have changed. These same tired complaints have been around for ages.

    If I wanted to know how much a student knew about chemistry, I wouldn't ask about trivia like what physical state mercury is in at STP. They can look that stuff up. I would personally be more interested in finding out if they can use the information in some constructive fashion.

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    1. I think sole emphasis on factoids encourages rote memorization rather than holistic understanding. That, needless to say, is a bad situation for chemical education because big boy chemistry problems require more than just facts.

      I don't, however, think education should focus solely on "can they use the information in some constructive fashion" because that's also silly. Some level of factual understanding is needed to provide context for certain problems. You need to know, at the end of the day, that triethylamine has a much lower pKa than methanol. You need some scope of how easily oxidized amines are. Totally dismissing factual knowledge as accessible at the touch of a button also discourages students from developing frames of reference.

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    2. *triethylamine as in (Et3NH)+

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    3. If they don't know that mercury is a liquid, then they probably didn't learn what STP is properly and why one of the usual measurements are called 'Torr', after the scientist who first used mercury to make a working barometer and measure pressure differences at different altitudes. This information is taught in high school and the point is made about the density of mercury and why water could not be used. To me it suggests that they also don't know what the term 'STP' means or even 'PV=nRT', and while I might let the mercury factoid go, this would be a huge warning sign to ask about at least those next two terms.

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    4. Are professors even allowed to keep their old rusty Mercury manometers anymore?

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    5. STP is used for gas volume calculations and not much else. But you can report gas volumes at any temperature you want, and 25 °C is also commonly used. So STP is not really a "standard"--certainly not in any thermodynamic sense. This confuses students when they later learn about thermodynamic standard states--they think temperature is part of the definition but it's not. I'd be perfectly happy if "STP" were never taught--it would be one less thing for me to unteach later on.

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    6. Sorry, but knowing the two elements that are liquid at STP is not trivia. Being deeply familiar with the periodic table is a (if not *the*) fundamental piece of knowledge that makes one a functional chemist. Any other conclusion is simply staggering.

      (now get off my lawn!) ;)

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  6. Organic Chemistry is not that difficult at all. It's nothing but an extension of acid-base chemistry from General Chemistry. If you can understand what a Lewis acid and a Lewis base are and you are able to comprehend that there will ALWAYS be "something" accepting electrons and something "donating" electrons then 3/4 of the battle is over and you are well on your way to understanding the lot of Organic chemistry. It was also important early on to recognize the functional groups, some basic reactivity principles that a high schooler could understand and the differences between a nucleophile and electrophile (fancy terms for Gen. Chem Lewis acids and bases again). I've always told students that when you see a large molecule, look for it's functional groups, label it as a lewis acid or base and then find the reactant(s) and label those as lewis acid or base and follow the electrons. You'll be able to figure out ANY organic reaction or at least come close to solving it. Most people classify the class as a med school weeder course and they defeat themselves before even stepping into the classroom. See Organic Chemistry for what it really is: carbon based lewis acids and bases. Physical Chemistry and Quantitative Analysis (which was a lower division course directly after Gen Chem II) were MUCH more difficult than Organic was.

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    1. I agree that O Chem is made to be much harder than it needs to be. I always wondered why most books start with reactions of alkenes and alkynes when pi-nucleophiles are actually much harder to relate to what you should already know from Gen Chem. Alcohols, amines, carbonyls would be a better place to start in my opinion.

      Back to Gen Chem: are there lone pairs in the valence? Probably a nucleophile! Or if you need it be an electrophile? Find something to accept the lone pair and generate a cation, voila! Cover that first, then explain that pi-bonds are kind of like lone pairs when it comes to reactivity.

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    2. My feeling is that what you're saying will be fine for the first 3/4 of the first lecture. BTW, nucleophile and electrophile are not "fancy" ways of referring to Lewis bases and acids respectively. They are the thermodynamic and kinetic definition instead. When it comes to radicals, stereochemistry, Grignard reagents et cetera, the plus/minus acid/base argument falls short pretty fast.

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  7. Ah, I thought of one:

    I once met a person who believed that senators were elected by district, i.e. some parts of a state did not get to vote for or against that state's senator.

    I consider knowing that a senator is represented to represent the whole state to be an "intelligence-essential fact about US civics."

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    1. Unless we start stripping natives of citizenship and deporting them when they can't pass a civics quiz, the response will be correspondingly... variable.

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  8. I do not understand the organic chemistry hate from the undergrads. I loved the subject and thought it was fun, but as a an instrumentation chemist, I think understanding of some instrumentation is important if you want a job in the western hemisphere. The number of instrumentation specialists/analytical chemists that I work with that have synthetic chemistry degrees are quite many. Bonus if you can you try to teach your students high throughput work and principle component analysis, which i think in a few years time will become essential.

    Considering how much time people spend looking for jobs, the interviewer shouldn't be surprised that people might be a little rusty when it comes to chemistry factoids. That said, those being interviewed maybe should start with a few wikipedia searches on the topics that are relevant to your perspective employer.

    I think you might be a little harsh about knowing, rather really just remembering, Mercury is a liquid. How much legacy Mercury equipment is left in chemistry departments? Do they even use alcohol thermometers anymore? Knowing Mercury is a liquid, to those that have never seen a mercury thermometer may be a little much to someone who just had to know it for five points on a multiple choice quiz.

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  9. See also: "Higher education bubble."

    Melanie Cooper and Fred Schreiber hit squarely on a major problem with the higher education system: Students are leaving unprepared. Who's fault is that? To suggest that some students have no business in higher education, let alone STEM education, is heresy. It certainly threatens the business model of most colleges and universities where tuition costs have outpaced inflation for at least a couple of decades and the number of "administrators" has risen sharply. Jack Nicholson said it best in 1989 (paraphrasing): "This [model] needs an enema."

    The model is unsustainable and will collapse. We are already starting to see the birth-pains of the collapse as students graduate with crushing debt and a degree that was "fun to get" but generally worthless to a potential employer.

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    1. For some reason, I, or Blogger double-posted the 0808 comment. Sorry.

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    2. The problem is that employers want someone else to train their students, and schools are (somewhat) complying. Any model that requires training in particular "job-ready" skills is going to leave students with a lot of debt for education that will (at best) make them employable for a short while (until they can be replaced by cheaper people elsewhere). The older model (that college was supposed to prepare people for a lifetime of learning - a general skill set that can allow them to do lots of different tasks) would be better but is less likely to render its graduates employable enough in the short term. Given that there doesn't appear to be any term in business other than the short term, I don't know what educational model will work (because education takes time, costs money, and values history).

      Administration has expanded because the value of education in this environment is inflated, and so their historical success at educating students is monetizable, and someone will want to go get some of that money. I think they're somewhat aware of the problems with their model - if they believed in education, then discarding the people who actually educate and replacing them with shorter-term teachers wouldn't make sense - the quality of their teaching (or their learning over time) must be irrelevant to do that. You only do that when you need to find a way to keep the money rolling in just a little bit longer, and beyond that does not matter.

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    3. What are you talking about? Blogger would never double-post anything.

      (At least it's not Corante's servers, which have (I hope) been recycled into something useful.)

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  11. I agree that tripping up an interviewee on factoids he/she has trouble recalling from undergrad gen chem might weed out interviewees who would make good employees, but some of the "intelligence-essential fact" questions can reveal a lack of fundamental understanding. One of my favorite job-interview questions is to have the interviewee draw SiO2 - someone who took gen chem, but doesn't have a deep understanding of the subject, will draw O=Si=O instead of tetrahedral Si!

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  12. Chemistry in general is a difficult subject. A certain amount of students do not like it when they have to work hard. My wife teaches general chem at an expensive private university. The students complain that in order to do well in the course they had to read the book. They complain that she does not collect homework problems and grade them, arguing that there is no motivation to do the problems if they do not get a grade. They complain that she told them that some of the elements are based on Latin words and you will just have to remember that sodium is Na because it comes from Natrium - they complained that she didn't explain it well enough and told them they have to memorize it. These same students fill out an evaluation at the end of the semester, which affects whether or not tenure is awarded. Orgo is a hard subject, and some instructors certainly are lousy (students didn't know what chirality was by the time they got to my wife's biochem class), but it seems like it's never a good idea to tell students that they are awesome and it's the professor's fault, because whether or not the prof. is good, you will still need to study. Maybe one thing they can do to help is not have the lectures at 8AM!

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    1. If it's being taught as a standard lecture and lab course, there are really only 3 convenient times to give the organic lectures: first thing in the morning; noon; or really late in the afternoon. Putting it at a more civilized time in the middle of the morning or afternoon means that the lab sections can't easily meet for the whole morning or the whole afternoon, depending. And when you're trying to cope with not conflicting with first-year physics or biology (a lot of the students will be taking one or the other, if not both of those) it becomes what the mathematicians call an ugly scheduling problem. At least that's how they explained it to me when I was an undergrad and TA. Of course, I rode a brontosaurus to campus...

      MG

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  13. I think there are two things that need to be emphasized when teaching orgo: 1. The logic 2. The real world relevance and applications. In my experience few teachers do this. A textbook like Clayden, Greeves et al. would go a long way in remedying both deficiencies.

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  14. Maybe the person lived in Alaska, where it is routinely colder than -38°F. For that person, mercury is a solid ;-) Chemistry is more than a compendium of scattered trivia. I wonder if Schreiber has any idea why mercury is a liquid (at STP).

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    1. It's because of Einstein: http://blogs.scientificamerican.com/the-curious-wavefunction/what-does-mercury-being-liquid-at-room-temperature-have-to-do-with-einsteins-theory-of-relativity/

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  15. I think this also represents a case where older, very experienced folks have forgotten what it's like to not be that way. My p chem teacher seemed to forget that we didn't have x amount of years doing this stuff or like ten different degrees in the subject. What's obvious to him isn't to a first timer. Likewise, whichever atom accepting electrons is obvious to an organic chemist who's been in the field longer than I've been alive. It's not as clear to newcomers.

    That being said, I found orgo to be a lot of fun for the most part. It's like a whole bunch of puzzles to solve. I and everybody else definitely had moments where we'd have never thought of the answer, but the teacher was under the impression it was pretty obvious.

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