The Maker’s mash, which they actually allow you to taste by dipping your finger into a fermenting vat, is 70% corn, 16% wheat, and 14% barley. Like other distilleries, Maker’s mixes a little bit of used mash in with the new stuff, to create a “sour mash” and ensure equal pH across batches. Yeast is added that converts the sugars in the mash into alcohol and carbon dioxide, which you can actually see evolving off the top of the liquid. The liquid mash spends three days in a massive vat made of cypress wood, some of which are over one hundred years old! Also, FYI, from personal experience…the fermenting mash is delicious.

After three days, the mash reaches 8-10% alcohol by volume, at which point it’s aptly called “distiller’s beer.” A double distillation process brings the alcoholic liquid up to 130 proof (65% ABV). Maker’s actually markets this stuff as unaged “Maker’s White”—the aging process introduces the familiar brown color and oaky flavor. Unaged bourbon is basically corn whiskey or moonshine.

The oak barrels used to age the whiskey are aged themselves for nine months in order to allow the tannic acid present in the wood to seep out. Maker’s uniquely rotates their barrels within the warehouse, so that alcohol spends about three years at the top and three years at the bottom. However, bourbon aging is not an exact science, as differences in the wood and alcohol can result in different “times to maturity.” Maker’s ages anywhere from five years, nine months to six years, three months.

Maker’s has a semi-automated bottling line; however, every bottle is hand-dipped in sealing wax before being shipped off. Workers dip roughly one bottle every three seconds, but rotate off the dipping line every thirty minutes. In the gift shop, visitors can dip their own bottles.

I honestly thought I was going to be bored out of my mind during this trip, but it turned out great. Highly recommended to any chemists interested in food chemistry out there!

Then I found PIHKAL, the story of Alex Shulgin’s life as a scientist studying psychoactive organic compounds. The second half of the book contains procedures for synthesizing a variety of phenethylamines. Notwithstanding your ethical take of Shulgin’s work, his procedures will make the Vilsmeier-Haack reaction stick to your memory forevermore. The reaction is central to Shulgin’s synthetic strategy—formylate an aromatic ring, then nitroaldol condensation followed by reduction provides the desired phenethylamine. The V-H reaction below is used in the synthesis of MDMA.

Most organic chemists have good stories associated with their favorite reactions. But what about “metaphorical” stories? Reaction mechanisms are the most common “metaphorical stories” of organic chemistry that come to my mind. Reaction mechanisms tell the tales of electrons, and figuring out how electrons are likely to behave in a never-before-seen reaction is a lot like figuring out how a fictional character would behave under new conditions. Take Captain Hook out of Neverland and plunk him down in a modern elementary school…I think we can all imagine what would happen! He certainly wouldn’t be friendly to the students.

Extending the “electrons as characters” idea, we can also imagine that the number of “plot elements” in reaction mechanisms is limited. There are a limited number of things electrons can do, when we take a sufficiently general view. However, there are countless variations on these themes, and a massive number of ways to chain steps together. Many students get the idea that these variations are what make organic chemistry hard. Yet…in both chemistry and the study of literature, seeing the forest through the trees—that is, recognizing when a new situation (story, reaction, mechanism, etc.) fits an existing general paradigm—is a critically important skill. The most interesting fictional characters live by general maxims, and we like to believe nature does too!

School has been crazy recently. I promised a post on chemoinformatics in education, and I will deliver soon…just not today I’ll leave you with an interesting problem from Alonso’s book, inspired by a recent post on MasterOrganicChemistry.com. Can you provide mechanisms that explain the formation of all observed products in the reaction below?

New post coming soon…

A little background first—as regular readers of my blog may be vaguely aware (assuming these “readers” exist), Science has begun to include science education studies in its pages lately. This is a very good thing. Not only does it put important research in the spotlight, it also attracts science educators to the journal, and an army of science educators who read Science is much better than one that does not! A recent educational research paper by Deslauriers, Schelew, and Wieman published in the pages of Science made some sweeping claims about improved learning in a large physics class thanks to a course intervention based on the idea of “deliberate practice.” Exam scores and attendance were both higher in the section that used deliberate practice; the “old school” section’s scores and attendance were lower. The sections were “matched” using several metrics, including the Brief Electricity and Magnetism Assessment and Colorado Learning Attitudes about Science Survey. Matched sections, differing only in the presence or absence of deliberate practice…everything seems peachy, right?

Not according to Derting et al. and Torgerson, who both wrote letters to Science criticizing the study. The bulk of Torgerson’s argument is that the study is not properly controlled, and does not take into account teacher effects (maybe the control group teacher just sucks in general, in addition to using “bad, old school” methods), selection bias, whether students knew they were being treated differently, etc. Derting et al. echo many of these points. One of their more intriguing ideas in common is that, really, the original study is the equivalent of a “single data point,” or a clinical trial involving a single placebo patient and a single treatment patient. Replication, echo the throngs of hard scientists, is needed.

The original authors responded by supplying evidence that their experimental design was good enough to be generalized. Randomized, hyper-controlled trials are not, they claim, necessary in collegiate science courses. Teacher personalities tend to not affect the amount of learning that occurs in collegiate courses (?!). Finally, they raise the point that replications of their experiment may introduce ethical issues, as investigators should expect to replicate their result, which would involve putting the control group at an intrinsic disadvantage.

Where to fall on this debate? It’s tough for me to decide. Both sides advance good arguments. Theoretical ideas and educational psychology research do support the practices used by the experimental section from the original paper. It would have been very bad if the authors’ results had not supported this existing literature, and what they did was almost certainly good from an educational perspective. However, like a sparrow sitting on a giant’s shoulder, the work does little to advance the field of physics education. There are some very subtle issues at play in the classroom, not all of which can be addressed by sweeping labels like “deliberate practice” and even “active learning.” Practical ideas that real educators can take away are hard to find in the paper, and that lowers its value. It’s a shame, because one can tell that their hearts are in it, but the long-term usefulness of the work just doesn’t stand up to scrutiny! The most valuable literature in education (at least to me) has always been the stuff with the most practical value. This paper will at best fade away and be remembered as little more than a blip on the radar—and at worst have a negative effect on the practicing scientist’s view of education research.