Bringing Real World Practice into an Organic Chemistry Class

Ron Rusay
Instructor
Department of Chemistry
Diablo Valley Community College
rrusay@socrates.berkeley.edu

Why use technology?
I do believe in technology as a teaching tool. I am doing my students a service by introducing technology to them and making it an integral part of my teaching. From serving on state committees, I've learned that--for the two-year college student, at least--there are two recurring skills that employers in California are looking for in their new hires. One is having a background in using the Internet. The other is being able to adapt to new technology.

I began using learning technologies in 1996, after joining the Modular CHEM Consortium (MC²), a project funded by the National Science Foundation (NSF) and intended to systemically improve the way chemistry is taught, and after attending a seminar at the University of California at Berkeley, sponsored by the National Center for Supercomputing Applications (NCSA). It was spectacular. The speakers

Chem 226. Chem 227. Modular CHEM Consortium. Lawrence Livermore National Laboratory Chime Pro® Chime® plug-in (free download) ISIS/Draw® (free download) RasMol (free download)

were a physicist, a chemist, and an artist, and they talked about the value of art and graphics in conveying information. It was one of the most powerful talks I have ever seen--the video of their presentation materials has been shown again and again.

At the seminar, I met a computer scientist who was working in educational outreach at Lawrence Livermore National Laboratory--in the years since, I have developed many close professional relationships at Lawrence Livermore. Laboratory scientists and staff have been invaluable in helping me exercise my imagination to its fullest in using technology in the classroom.

But it hasn't been easy. The community college environment in California is complex. Diablo Valley College is regarded as one of the better institutions of the California community college system, which has 107 two-year colleges and over 1 million students enrolled statewide. DVC has 22,000 students; about 10 percent matriculate in chemistry each year. However, although there is a high level of professionalism here, the culture doesn't put a high value on outcomes other than test scores; rather, instructors teach to content, with an emphasis on informational learning, not critical thinking. There are few or no rewards for teaching innovators, in learning technology or otherwise.

The strategy
My quest in teaching innovation began as a crusade, and now it is sort of an individual, self-rewarding enterprise. When I started, many things came together at the right moment in time. I came back to teaching after 15 years working in research and development as a synthetic chemist in industry. I had always valued educators, and I returned with a really idealistic vision. But I understood how difficult it is to deal with long-embedded cultures, such as the ones found in education.

At the same time that I was hearing about new pedagogical theories and methods of teaching through the Modular CHEM Consortium, my wife was getting a master's degree in education. I was learning the lingo through her just enough to be dangerous. And my colleagues at the Lawrence Livermore National Laboratory began providing me with the computing wherewithal, the servers, the software, and whatever else I needed to accomplish my educational pedagogical goals. I had a sabbatical year in 1996. That is when everything came together. I was a reviewer of the National Research Council's report, "Transforming Undergraduate Education in Science, Mathematics, Engineering, and Technology," and I was ready to put my ideas on teaching innovation into action and to help change the system to boot. I had an aggressive plan, and I accomplished more than I'd planned. I introduced visualization and modeling software, specifically designed for chemistry, into my class, along with access to professional databases--a key element in organic chemistry is translating a three-dimensional world to a two-dimensional world, to think that way and relate it to the real world. I got involved administratively, chairing the college technology committee, because my students didn't have any computers to work at. I devised a "metacognitive," constructive approach, which was a radical departure from traditional linear learning. But I had little luck recruiting other converts to using learning technology and creating more systemic change. After working my way up to the state level on these issues, I retrenched and decided to concentrate on my classes and students.

An example project: I have my students first complete a library research project; it starts on my campus where we have certain search tools. The students will generically research a class of chemicals, like antibiotics, and get a framework for that chemical's historical progression--and also the current issues that are involved. For antibiotics, that would most likely be resistance. And for two weeks they have full access to the UC Berkeley Chemistry Library: the chemical abstracts, electronic journals, etc.

After they get a general description, they are asked to select one compound that they think would be the most important compound in that class and then provide me with a synthesis for it. While they can't do screenings of the libraries of compounds that exist out there, they can work at a very elementary stage and begin to understand what chemists in industry do now to create new compounds. And to relate it to the course, they have to cite three references in their textbook that match up to the synthesis--three reactions. They have to outline the construction of a molecule that someone has created, but they have to relate it to what we're studying on a theoretical basis--this step is an oxidation, in this step a carbon-carbon bond was formed, etc. At the end, they submit two copies of their papers; they're divided into editorial groups that read and rank each paper, and select the ones most worthy of being published on the Web. I then put three papers up on the Website.

The course
The classes, introductory courses in sophomore organic chemistry, use a one-year sequence, with three hours of lecture and six hours of lab. The course is totally web-accessible for syllabi, selected readings, and lab work. Nothing is password protected. It's free for everyone to access; visit the first semester organic course, Chem226, or the second semester organic course, Chem227.

The learning technology
I try to get my organic chemistry students to think in three dimensions on a molecular level, and I try to introduce as much real world practice into the classroom as I can. To do that, I've pulled together a variety of visualization software tools, plus crucial access to databases on the Internet.

Chime Pro®: Developed by Chime Pro® is a chemical structure visualization application that runs in Netscape Communicator® or MS Internet Explorer®. Users can render chemical structures and then visualize them in animated Java applications and applets, besides rendering the structures as Web pages. Chime displays dynamic chemistry models electronically, rather than static pictures of molecules. A plug-in for the software allows users to search for particular chemical structures across a variety of chemical databases. Find out more by visiting MDL.

RasMol: RasMol® is a free application that displays the structure of molecules, showing DNA, proteins, and smaller molecule structures. It can also be used as a research tool. The software provides full-colored, three-dimensional images. A related software, Protein Explorer, allows you to rotate a protein or DNA molecule to show the 3D structure. You can download RasMol for free.

ISIS/Draw®: Described as a "chemically intelligent" drawing package, ISIS/Draw (download ISIS/Draw® for personal or academic use free) allows you to draw structures just as you would a paper sketch and insert the sketch into various documents and programs. Find out more by visiting MDL.

I provide students with access to databases of chemical structures, Chemfinder®, and MSDS (material safety data sheet) web sites (one website, has a nice list of free MSDS web sites). DVC now has 150 computer stations available on campus, with all the needed software; all are Internet accessible. We substitute the wet lab with computer exercises and generally take the whole class into the computer room for lab. I use various CDs with visualizations in lecture.

I also put up a FileMaker Pro® Web-accessible database, and I have a Web board that goes with it. We recruited faculty to participate from three other colleges; the first round of recruiting brought in 10 percent of full-time faculty. I thought that was pretty good, but it's now been 14 months and it hasn't grown, which is troubling.

Here are some additional links to try:

Chem 227: Some photos of students' protein artwork

Chem 227: An interactive activit:

Chem 227: Assignments and activities

Chem 226: Smell and stereochemistry

Chem 226: Molecular Modelling I

Chem 226: Chemical Communication: Introduction to Pheromones

Chem 226: Molecular Modelling II: Conformations