Chemical Education Roundup, 12-11-12

As the weather has turned cold (or not), what’s new in the chemical education world? A number of interesting articles have been published this fall. Bruce Albert’s editorial in Science about the damaging effects of shallow learning in science education is a good place to start—using a personal anecdote about his grandson’s biology textbook,  Alberts laments the “breadth not depth” approach to content you see across all levels of science education.

Close to my own heart, Marc Loudon and Laurie Parker have published an interesting study of online homework in an organic chemistry course, concluding that studying textbook problems in addition to solving online homework problems provided no benefits to learning versus solving online homework problems alone. From their abstract: “We speculate that this is because the immediate feedback given by the online system more effectively reinforces the topics.” In other educational technology news, Churchill has written recently about design considerations for learning objects that promote exploration and learning of concepts, conceptual model learning objects. Using data from several different studies, he recommends a minimalist design paradigm: design for a small screen, use a single font, avoid audio/video unless they’re the only option, don’t use too many different colors, etc. Structurally, he advocates the logical use of frames to divide up screen space. Another theoretical study using a “Nature of Technology” approach provides design pointers based on philosophical and cultural ideas.

MOOCs continue to dominate the “popular education” scene, although formal studies on MOOCs haven’t yet emerged—look for that to change in the next six months.

In science writing and inquiry news, a study of argumentation in general chemistry laboratory reports has recently been published. Students used the Science Writing Heuristic approach, and the researchers deconstructed students’ arguments to identify their most important elements for performance. Scientific inquiry itself came under the data-mining microscope in a recent Int. J. Sci. Educ. article, which used cluster analysis to examine types of scientific inquiry in a collection of scientific studies.

Other highlights: a fascinating look at physics teachers’ emotions while implementing inquiry-based activities, a learning progression for energy, the importance of speaking up for learning in an active learning classroom, and an item-reponse-theoretical treatment of an international science/math skills assessment.

#ChemCoach: My Story

Hey all! This is my contribution to See Arr Oh‘s ChemCoach project. Interested in what a chemical educator does all day? How I got here? Stalking me? Whatever it is, you’ve gotten this far; keep reading…

What would you say…ya do here?

I’m currently a graduate student studying organic chemistry and chemical education at the University of Illinois, Urbana-Champaign. I also work part time as a Graduate Affiliate at UIUC’s Center for Teaching Excellence, teach CHEM 332 (Elementary Organic Chemistry II) at UIUC, and run the website + create content for Organic Reactions. Most of my time is spent teaching and preparing materials for teaching…but then again, I have a very flexible definition of what counts as “teaching materials,” and my teaching and research practices often overlap (more on that later). I strongly believe that chemical education researchers should also be good teachers, and if they aren’t good teachers, they’re “doing it wrong.” You’d be surprised how many brilliant chemical education researchers fit this description…but that’s a tale for another time. My research involves the development and evaluation of educational technologies for organic chemistry.

Take us through a typical day…for you.

A “typical” day can vary for me, but here’s a broad overview. I teach at 8 am on Monday, Wednesday, and Friday, which forces me to get to work by 7:30 on these mornings. After I teach, I generally deal with teaching responsibilities and preparing materials for teaching in the morning—it’s just a weird habit I’ve gotten into. In the early afternoon I’ll do CTE stuff: meet with TA’s, do class observations, prepare presentations, eat the world’s most delicious mints (seriously, they’re like crack for me), etc. The later afternoon and evening are usually reserved for research. My research responsibilities vary somewhat across projects, but I’ll go through alternating periods of creating content, writing code, collecting data, and carrying out data analysis. As I’m not a computer programmer by trade (although I always loved it), writing code probably takes me the most time…it’s a toss-up between that and drawing flippin’ structures in ChemDraw. Many of the products of my research are turned back over to students—to help them overcome difficulties, work more intimately with molecules, etc. There is one constant in my day: coffee.

What kind of schooling, training, or experience helped you get where you are?

I graduated from the University of Kentucky with a B.S. in Chemistry, and I can’t say enough about how my experiences there (good and bad) inform my teaching and research. During my time there, I fell in love with teaching, and jumped on an opportunity to serve as an undergraduate workshop leader for organic chemistry at UK. Advice for those who want to become chemical educators: start early. There’s a tired old fogey out there waiting for your youth and enthusiasm. Start reading the literature and critiquing the literature early, before you “get” everything—do not fear the chemical literature. It’s just vicious rumor, after all! Once at UIUC, I took a course on college teaching that opened the door to opportunities at the Center for Teaching Excellence, and I’ve been networking with other faculty and academic professionals on campus interested in teaching ever since. Again, you’d be surprised—there are more of us around than you think.

This seems like a good place to warn you that being a great chemical educator is not for the faint of heart. My committee is 75% “wet organic chemists,” and dealing with them is not an easy experience. You will be misunderstood, ridiculed, kicked when you’re down, and marginalized throughout your career—however, this is not an excuse to shy away from these experiences! On the contrary, value your interactions with practicing chemists. This is perhaps the most important thing graduate school has taught me. If you just want to crawl into a hole and teach, you’re part of the problem, not the solution!

How does chemistry inform your work?

Naturally, organic chemistry is central to what I teach. My exam problems come from the chemical literature, and I read journals daily. Chemistry is also central to the way I develop software: I think about how to “systematize” chemical principles so they can be encoded in computer programs. I consider how software can help students create and work with chemical structures more efficiently. I think about how machine-readable chemical data can expose common misconceptions and help students spot their weak areas. The list goes on, but thinking about the relationship between chemistry and technology fascinates me. The future is bright!

A unique, interesting, or funny anecdote about your career

So many stories…goodness. I think I hold the UIUC record for most hours spent on video on campus—I’ll even take the journalism department to task on that. I’ve recorded online videos for both non-major organic chemistry courses (approaching one thousand students per semester), so I get a lot of weird looks walking across campus, which I do almost every day. Once, a student ran up behind me on the quad and poked me on the shoulder…she had recognized me by solely by my voice! In the live classroom, I tend to be rather brash and vulgar. For example, what some would call “figuring out the bonds made and broken in a reaction,” I affectionately refer to as “cutting out the bullshit.” I also enjoy anthropomorphizing: past activities include “your hands are enantiotopic,” “surf’s up with pericyclic reactions,” and “the human orbital diagram.”

I blog here (naturally), and I keep my organometallic skills sharp over at The Organometallic Reader.

Chemoinformatics Curiosities: A Chemical Educator’s Perspective on InChI

Organizations supporting machine-readable molecular formats.

Organizations supporting machine-readable molecular formats.

When it comes to machine-readable representations of molecules, I grew up with SMILES. A SMILES string reflects the connectivity and stereochemistry of a molecular structure, and may be generated from any number of other machine-readable formats, such as MOL and CML. SMILES strings are becoming ubiquitous on the web, thanks to giants like Wikipedia. They’re nice because they’re fairly short and readable—the SMILES string for ethane is simply “CC,” for example.

That said, the limitations of SMILES are difficult to ignore. The same readability that makes SMILES appealing to human eyes limits its scope significantly. The innards of the SMILES algorithm(s) are fairly simple from a chemist’s perspective, and do not take into account spontaneous structural changes like tautomerization (or even the structural equivalence of resonance forms). There are multiple algorithms, meaning there is not, strictly speaking, a one-to-one relationship between structure and SMILES string. Finally, SMILES is a proprietary format whose algorithms are kept under lock and key—with the notable exception of the OpenSMILES project.

IUPAC, chemistry’s own group of nerds with a nomenclature fetish, has been working to remedy this situation for over a decade. Their machine-readable format, the International Chemical Identifier or “InChI” (en-chee), reflects a completely different philosophy from the SMILES approach. The goal of InChI is not to fully represent molecular structure, but to generate a unique identifier for a particular compound, given a structural representation. The InChI folks recognized that molecules can be represented with varying levels of detail, and that we may not necessarily need all the details to uniquely identify a particular compound. Many species, for example, can be singled out by their molecular formulas and connectivity alone. H2 is a nice example—to uniquely identify H2, all we really need is its molecular formula and knowledge that the H’s are bound together. More complex compounds, such as those that may possess stereoisomers, need more details in their identifier. Continue reading →

Chemical Education Roundup, 7-22-12

Has it really been almost a year since I last published a roundup? Wow. I confess that I’ve been putting much more effort recently into another project, The Organometallic Reader. With BCCE 2012 coming on soon, it seems an appropriate time to start the roundup train going again. I can’t make it to BCCE this year, unfortunately, but the e-program looks fascinating. Follow my man Jeff Raker on Twitter for nods to talks he finds interesting.

So what’s new in the world of chemical education research? What are the cool jams? What is everybody up to? Here are some of my favorite papers over the past year, in no particular order.

On the theoretical side, all organic chemists should check out the hybrid orbital controversy that erupted in the pages of J. Chem. Educ. earlier this year. At issue is whether hybrid orbitals are “real” and whether they should be taught to general and organic chemistry undergraduates. Rebuttals to the original paper brilliantly come to the defense of hybrid orbitals. As an educator, I feel more confident teaching and discussing hybrid orbitals with students after reading this series.

I’ve been waiting on this one for a while: in April, Grove & Cooper’s article on representational competence while drawing organic reaction mechanisms was finally published. Although the papers’ results left me wanting more, the authors’ conclusions will resonate with any organic chemistry teacher. They found that many students avoid using mechanistic approaches to solving organic chemistry problems when mechanisms are not the direct goal, as in “predict-the-product” questions. However, among students who did draw mechanisms, a disturbing trend emerged: the proportion of students who drew nonsensical mechanisms containing cyclic electron flow actually increased with time! On the positive side, the most notable trend over time is a decrease in “nucleophile-attacks-nucleophile” and “electrophile-attacks-electrophile” mechanisms. Still, the (understandable) disrespect that students develop for physically correct mechanisms over time is staggering. Organic chemical educators must be relentless! Continue reading →

Chemical Education Roundup, 8-16-11

It’s been a while since I’ve done a roundup! The world of chemical education has been relatively quiet over the last month, although a few interesting things have happened (mostly in education-at-large). A while back, I blogged about Moskovitz and Kellogg’s intriguing idea of “double-blind science writing“—setting up laboratory experiments and reports so that neither students nor graders had an expectation of what their results should be. The aim of the exercise is to rip the bed of procedural and predictive comfort out from under students’ (and graders’) feet. Such a setup, argue the authors, forces students to use well-supported, rational arguments in lieu of the regurgitative, droning garbage that one usually sees in lab reports, and forces graders to evaluate students’ arguments as arguments—just as they would evaluate an academic paper.

On July 29, Science published a brief retort to the Moskovitz paper by Michael Goggin, a physics instructor who argues…

The first priority should be ensuring that the students get the correct result; their ability to articulate that result is secondary. (emphasis mine)

Goggin’s stated objection is that Moskovitz’s approach aims to teach writing more than science. However, in my opinion, a sufficiently open-minded scientist should take issue with Goggin’s assumption that the ideal lab experiment has “the correct result.” On the contrary, conservative experiments with spelled-out “correct results” lead students to believe that a career in science consists of proving what is already known. As any blue-blooded scientist knows, the opposite is true—most scientists spend their careers convincing others that their work is new! The work of undergraduates does not have to be new per se, but it should be new enough to them that constructing a convincing argument requires learning, not just regurgitation. Moskovitz’s approach to scientific writing is thus a step in the right direction. In a response to Goggin, Moskovitz and Kellogg offer this argument and others (among them: lectures give ample opportunity for students to find “correct answers”) in support of their ideas.

A little closer to home for me personally, Neil Selwyn has written an intriguing editorial in the British Journal of Educational Technology about the need for “pessimism” in the field. I put “pessimism” in quotes because what Selwyn argues for is less pessimism and more “healthy skepticism.” Selwyn states (truly) that there is an obsession among educational technologists with the use of technology as representing “progress” in education. Technology use seems to be associated with progress everywhere else in our lives—why should education be any different? Of course, in all aspects of human life, technology has its downsides. Selwyn argues (again, truthfully) that educators that use technology are often blind to the limitations, pitfalls, and “everything old is new again”-ness of what they do. How much in educational technology is actually new, he asks? Less than we think. ETs need a fresh challenge, a kick in the pants, a wake-up call that alerts us to the fact that what we’re doing may not be all it’s cracked up to be—which could be a good thing! Connections to past scholarship (and challenges to move beyond it) will only do good for the field of educational technology in the long run.

Other news and editorials: an interesting study of central nervous system drugs using calculated electrostatic potential energy surfaces, the harsh realities of narcissism and grade inflation, and a piece from the EIC of the Journal of Chemical Education on striking a balance with assessment. If you haven’t already, read about the epic standardized-test cheating scandal in Atlanta referenced in the last article.

Chemical Education Roundup, 7-4-11

Happy independence day! A brand-spanking-new issue of Chemical Education Research & Practice found its way into my RSS reader list this week, so there’s plenty to talk about for this week’s roundup.

Let’s begin with a paper that gives multiple-choice tests in chemistry a second look. A lot of educators are nagged by the feeling that multiple-choice tests focus on factual understanding and memorization rather than conceptual understanding. One reason for this, argues George DeBoer in a recent CERP paper, is that typical analyses of multiple-choice tests treat them as dichotomous—every answer is either right or wrong, and the incorrect choices are lumped together and thrown out. In most cases, however, instructors deliberately design incorrect items (also known as “distractors”) to highlight incorrect lines of reasoning. If this is the case, we have a lot to learn from incorrect answers!

DeBoer applied Rasch modeling to a series of multiple-choice tests whose distractors were designed to pinpoint common chemistry misconceptions. Like item response theoretical models, Rasch models assign ability levels to students and difficulty levels to problems. The probability of a correct response on item x by student a is related to the difference between a‘s ability parameter and x‘s difficulty parameter. DeBoer’s model is even more finely grained, as it specifies probabilities for each choice on each item. Because each choice highlights a different misconception, one can plot the relationship between overall ability level and the probability of exhibiting some misconception (e.g., see the graph below). Cool stuff!

Misconceptions as a function of ability level

In other news, Penn et al. have validated the usefulness of concept maps as a measure of understanding in organic chemistry, using correlations to problem-set scores and final course grade. To generate the maps, they used a freely available concept-mapping tool called Cmaps.

The Journal of Computing in Higher Education has begun a special issue on interactions in distance education, and the first paper from that issue folds together two studies that address how different instructional strategies facilitate group interaction in online classrooms. The studies used the SOLO taxonomy and Community of Inquiry framework to evaluate instructional strategies; the results were largely complementary and fit together nicely in Kanuka’s article.

Finally, check out my friends’ blog on surviving in the wonderful, wild midwest at Adventures in the Midwest!

Chemical Education Roundup, 6-24-11

As I was getting in touch with my inner tribesman this week, the world of education continued its slow march towards (in the general direction of?) enlightenment.

Got to continue to give mad props to Science for bringing educational issues to their pages. In the June 24 issue, Stipek reminds us of the importance of creating positive educational experiences for students in high school and college, by avoiding “teaching to the test” and creating collaborative, not competitive, classroom environments. If you’re interested in how educational researchers envision the ideal classroom today, it’s a nice summary of techniques and strategies.

On the educational technology front, JCE has published a short but powerful article on the use of GNU Octave (think open-source Matlab) to simulate experimental data for instrumental analysis labs. Octave generates the data, the instructor specifies calculations that students should perform, and Octave is able to evaluate the results of students’ calculations. One can imagine using this for some interesting “data pooling” applications, without the complicating factor of experimental (operator or otherwise) error.

In another recent JCE article, Abriata laments the woeful state of circular dichroism in undergraduate chemistry education. For the article, he developed a simple spreadsheet algorithm that simulates the CD spectrum of a protein based on its secondary structural content, using the simple assumption that the CD spectrum of a protein is a linear combination of the CD spectra of its most common secondary structural elements (alpha helices, beta sheets, and random coils). The spreadsheet can also fit a curve to an experimental CD spectrum to determine the approximate secondary structural content of a protein whose CD spectrum is known.