Guest Post: “Google Glass and Twitter for Chemistry Education” by Arash Soheili
Aug06

Guest Post: “Google Glass and Twitter for Chemistry Education” by Arash Soheili

Today’s guest post is from Arash Soheili, a postdoctoral researcher at the University of Texas, Southwestern Medical Center. As curator of the Twitter account @Total_Synthesis, which is turning 2 this month, no new total synthesis in the journals escapes his watchful eye. He’s passionate about teaching chemistry. And we’re jealous of him because he got to visit Google’s NYC offices to pick up his very own Google Glass. Check out his tech musings at Android Cowboy. I love organic chemistry and have been practicing it in academia and industry for over a decade. I’m also a huge fan of technology and strongly believe that there is a place for it in chemistry education. In fact, I would even say that in the next decade it will become a necessity to incorporate technology as part of the formal teaching toolkit. That process is already happening informally with so many educational videos on YouTube from enthusiasts and educators. But so many technology tools are constantly changing and it will take a strong effort on educators to find the methods that work best. Just like running an experiment in the lab, it will take planning, as well as some trial and error, to get the best results. My personal experience with chemistry and education started about two years ago. I wanted to find a way to reach more people and introduce new and interesting topics in chemistry using existing social networks. My passion for natural product synthesis led me to start a total synthesis Twitter feed. I check all the major organic chemistry journals daily and tweet any completed total synthesis of a natural product that I find. If you are interested in natural product synthesis then you can easily follow the Twitter feed and be up to date. You can also join the conversation by using the hashtag #totalsynthesis. The idea was very simple, but it had yet to be executed. Now in two years there are close to 1000 followers and it serves as an archive of over 400 natural product syntheses in all the major journals. This information would be hard to collect and very laborious using the typical search methods like Google, ACS, SciFinder, etc. It is an idea that can be duplicated for any other topic of interest in science and can be even tried in a formal class setting. Similar ideas include the online Twitter #chemclub by Andrew Bissette. Social media tools are far from the only game in town. Hardware tools have huge potential for application in chemistry education. One example is Google Glass which is basically a head mounted computer with the ability to...

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Student Video Competitions Continue To Heat Up
Jul03

Student Video Competitions Continue To Heat Up

It seems like it was just yesterday that Newscripts started receiving student-made YouTube videos about organic chemistry. But two years have gone by, and the crop of clips--and universities that produce them--keeps growing. In 2010, Neil Garg, a professor at UCLA, gave the students in his organic chemistry class an extra-credit assignment: Write, direct, and produce a music video about the topics covered in class. He expected only a couple undergrads to take him up on his offer, but he received 60-some clips in the end. The video above came out of Garg’s class this spring—a parody of both the Beastie Boys’ “Paul Revere” and 50 Cent’s “PIMP.” (The Lord of the Rings references, Garg explains, are a little class joke. Because of all the aromatic chemistry the students learn during the semester, they get the title of “Lord of the Rings” if they get the top grade on an exam.) The video assignment has picked up so much momentum at this point, Garg tells Newscripts, he couldn’t imagine not offering the bonus project to his students. “Students will be disappointed if I don’t continue,” he says. Via word of mouth and examples online, “they know it’s coming.” And, he says of the assignment, “as long as they still enjoy it, and they seem to be learning something, it’s worthwhile.” Professors at other universities have found it worthwhile as well. Earlier this year, Jon Rainier of the University of Utah and Steven Castle of Brigham Young University cooked up a friendly Utah State rivalry between their organic chemistry classes with a video contest. Each chemistry professor gave their students the extra-credit music video assignment based on the UCLA model. Then they submitted their top 5 entries to Garg himself. Garg and a group of students were supposed to declare the winning class. “But I took the wimpy way out” and called it a draw, Garg admits. “It was a bit of a cop out,” Rainier says of the decision, especially because the professor from the losing class was supposed to visit the winner’s class and sing that school’s fight song. “You can imagine the anticipation.” Even though an official decision was never made about the class submissions in general, one video did rise above the rest. That much was agreed upon by Garg and the others. That clip, made by a student in Rainier’s class, is entitled “Meso” (see above). It celebrates meso compounds, those special stereoisomers that have two chiral centers but are not optically active themselves. The student responsible, Spencer Merrick, is a fine arts major taking chemistry on his path toward med school, Rainier tells Newscripts. The song...

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Amides: Humble But Useful
Sep15

Amides: Humble But Useful

A heartfelt thank-you to Chemjobber and See Arr Oh for helpful discussions! CENtral Science’s benevolent overlord, Rachel Pepling, has organized a blog carnival around the theme of "your favorite chemical reaction". For the Haystack's contribution, I thought it would be appropriate to write about a reaction medicinal chemists might find familiar. So I re-read See Arr Oh's post about which types of reactions were really the most common in the med-chem toolkit. I decided on amide formation, which sits just about at the top of the list. I’m not sure it’s my favorite chemical reaction; I’ve got a special place in my heart for the Heck reaction (or Mizoroki-Heck reaction), though I’ve already blogged extensively about it. But every amide bond formation I ran in grad school worked. That’s justification enough for me! Amides are the chemical ties that bind amino acids together to form peptides and proteins. Amides also turn up in a variety of other small molecules that nature makes. So it's not surprising that amides are frequently found in drugs. Take a look at University of Arizona chemist Jón T. Njarðarson's poster of top brand name drugs and marvel at the amide-y goodness. Amide bond formation isn't accomplished by a single, archetypical chemical reaction-- far from it. I thought I'd provide a brief overview of some classic chemistry in this area and then move into a selection of modern-day additions to the amide-construction toolkit. At first glance, it looks like all that’s needed to make an amide is to combine a carboxylic acid and an amine. But to make those two components come together, chemists have had to grease the wheels a bit by activating the carboxylic acid. Converting the carboxylic acid into an acid chloride or acid anhydride are among the oldest of the old-school methods for this. In 1955, MIT chemist John C. Sheehan reported a different idea—use of a coupling reagent, dicyclohexylcarbodiimide (DCC). Classics in Total Synthesis notes that in its time, DCC was "an important advance in the state of the art for forming amide bonds." In fact, Sheehan used it, along with the base potassium hydroxide, in the critical final step of the first total synthesis of penicillin-- construction of the beta-lactam ring of the molecule. However, separation of byproducts from the desired amide can be a limitation of DCC, according to the Haystack's intrepid guest blogger See Arr Oh. Today, "O-chemists have newer, sexier reagents," See Arr Oh adds. Those reagents include N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC), a next-generation version of DCC that's water soluble, and other classes of activating reagents including uronium and phosphonium reagents. John Pokorsi, a student in Karl...

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Special Delivery For A Synthesis Victory #ACSDenver
Aug30

Special Delivery For A Synthesis Victory #ACSDenver

When John Wood read about the first total synthesis of N-methylwelwitindolinone C isothiocyanate, he was impressed. After all, the densely functionalized welwitindolinone family of alkaloids has been in synthetic chemists’ crosshairs for the better part of two decades. Fifteen different labs, including Wood's own at Colorado State, have published over 20 "progress toward" papers on one subset of welwitindolinones alone. And this particular natural product, with intriguing bioactivity on drug-resistant tumor cells, has proven to be among the most desirable targets. Once he really studied the synthesis (J. Am. Chem. Soc., DOI: 10.1021/ja206538k), presented today at ACS Denver by UCLA’s Neil Garg and his grad students Alex Huters, Kyle Quasdorf, and Evan Styduhar, he decided the work merited more than just the customary “Nice job” email that floats between professors as a means of congratulation. Fortunately, he knew just what would fit the bill. “A few years ago as part of a woodworking project I was doing I learned how to sandblast images onto glass,” Wood says. “I was so taken with Garg's synthesis that after I read it I went home and sandblasted the image of his retrosynthetic scheme onto four beer glasses,” one for each team member. He then shipped the package to California, where an unsuspecting Garg received it in his office. “I called the students in before I opened the box,” Garg says. When he pulled the package open, it contained the four glasses, carefully decorated with the team’s names and their chemistry. But the box held something more. “There was a nice card and a $20 bill in there,” he recounts. In the card, Wood advised Garg to use the $20 to take his students out for a beer as they deserved it on account of their fine work. “This is a really competitive field, so it’s been great to have support” from the community, Garg says. He notes that his own Ph.D. adviser, Caltech’s Brian Stoltz, worked on this same natural product family as a graduate student with Wood. The $20 was spent as instructed, Garg reports. “But nobody wants to use the glasses because they’re really...

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A Virtual Chemistry Flashcard App
Jun26

A Virtual Chemistry Flashcard App

We love chemistry iPhone apps here at C&EN-- and we've received word that a new one is arriving soon. So we're giving you a sneak peek at that app, Chemistry by Design, the brainchild of University of Arizona associate professor Jon T. Njardarson. Chemistry by Design is essentially a virtual flashcard system, designed to help students and full-fledged chemists alike learn the graphical language of organic synthesis by studying the step-by-step blueprint chemists used to arrive at complex natural products, and even some small-molecule drugs. Right now there are 202 total syntheses included in the app, adapted from publications dating as far back as 1956. Call it "Classics in Total Synthesis" for the iPod set. While the app lacks the prose that guided chemists through that well-known series of books, it intends to make up the difference with interactivity. A user can "hide" reagents, starting materials, or product structures in each step of each total synthesis in the app. "That generates different kinds of questions," Njardarson says. Chemists can quiz themselves on different parts of a total synthesis, or they can simply browse. Njardarson and his students developed the app in about four months, with programming support from the University of Arizona's Office of Instruction and Assessment (OIA). "I had the idea four years ago," but the support from the OIA was was really made the program possible, he adds. He hopes that chemists will be willing to contribute their own syntheses to the app, and has provided instructions for submissions. This blog post is not technically a sneak peek, since Njardarson launched Chemistry by Design on the web just this weekend. You can check it out right now if your heart so desires. But the web version won't work on the browser on your favorite iDevice, because it uses Flash. You'll have to wait for the app's premiere at the Apple App Store in a few weeks to do that. Njardarson says the app will be available free of charge. Find prior chem app coverage here, here, and...

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