Beilstein Commander, SciFinder Scholar, and Google

1. Beilstein Commander, SciFinder Scholar, and Google Lyle Isaacs Department of Chemistry and Biochemistry University of Maryland College Park

2. MY TEACHING PHILOSOPHY / GOALS • Faculty members should act as seasoned guides to teach students how to ask their own scientific questions, how to answer them using current tools, and how to communicate the results. • Teaching through research. • Show students how a practicing organic chemist thinks. • When I started at the University of Maryland I was struck by the disconnect between the way I learn and the way we teach. • Reasoning by analogy, rules of thumb, etc. • The use of online databases as self-teaching tools was non-existent. • Given that I have room for only a couple of students in my laboratory per semester, how can I engage the majority of students in “learning through research”? • 2-minute essays • Group problem solving • Online databases as a powerful self-teaching tool.

3. CHEMISTRY 247 ASSIGNMENTS • Chemistry 247 is second semester organic chemistry for majors. • Four Online Exercises at 17.5 points each (out of 1000 total) • Investigate the generality of the Williamson ether synthesis • Compare and contrast the ease of obtaining information regarding cucurbituril using SciFinder, Beilstein, and Google. • Devise a cocaine synthesis from commercially available materials. • Explore the generality of your favorite carbonyl condensation reaction from Ch. 23 of McMurry. • Final Paper (100 points) • Must ask a scientific question and use either SciFinder or Beilstein to answer that question.

4. SEARCHING WITH SCIFINDER

5. COMPARE AND CONTRAST GOOGLE, SCIFINDER, AND BEILSTEIN In this exercise you should search for chemical information regarding cocaine using the 3 search tools. 1) What is the structure of cocaine? 2) How is it synthesized? 3) What are the physiological effects of cocaine? 4) Compare and contrast the ease / difficulty of actually using each search tool. 5) Comment on the relative quality of the search results obtained by each search engine (e.g. are they up-to-date, are they relevant, is the information accurate, etc.). 6) Which search engine is most appropriate for gathering chemical information?

6. A SELECTION OF STUDENT PAPER TOPICS (what happened to rock and roll?) • Viagra: How is sildenafil synthesized and how does it work? • The action of pheromones in a honey bee colony • A Synthesis of Lysergic Acid • Total Synthesis of (-)-a-Thujone • The Drugs Behind Lethal Injection • The Effects of Mustard Gas • Synthesis of polyesters • Chemical structure and synthesis of Silly Putty.

7. GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS Google/ Internet Text / TA Prof / Lib. SciFinder + Internet SciFinder alone 1. How did you approach researching a chemical problem before the semester started? 2. How would you go about researching a chemical problem in the future? 3. Was the amount of time invested in the online database exercises commensurate with the amount of learning that took place? 73 3 27 9 0 21 0 68 Yes Maybe No 70 17 13

8. GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS STRONGLY DISAGREE STRONGLY AGREE 1. The instructor adequately explained how to use the online databases for the exercises in this course. 2. The exercises helped me see the generalities of organic chemistry rather than focus on the differences. 3. I learned how to use the online databases to ask and answer my own chemical questions. 4. The online database exercises were a worthwhile addition to this course. 5. The exercises made me more aware of the need to evaluate the relevancy of information obtained from online databases. 6. I am better able to distinguish between a question that is likely to have a clear-cut answer from one that is vague. 7. In the future I will use Google to help answer my chemical questions? 8. In the future I will use SciFinder to help answer my chemical questions? 9. In the future I will use Beilstein to help answer my chemical questions? 10. The online database exercises helped me see how a practicing organic chemist actually thinks. Q# 1 2 3 4 5 6 7 8 9 10 A B C D E 33 5 2 33 28 6 38 14 38 13 8 28 18 9 40 15 30 20 8 2 31 17 5 2 30 35 11 2 36 44 10 8 2

9. A SELECTION OF STUDENT EVALUATION COMMENTS • “The course gave me a better understanding of chemistry and allowed me to better relate it to everyday life.” • “He asked questions of the class and allowed us to discuss them amongst ourselves rather than just telling us the answer. I think that was great.” • “Dr. Isaacs would ask for 2 minute essays at the end of class that he would address at the beginning of the next class to be sure everyone got the concepts. I’ve found it very innovative and helpful. • “There weren’t really any weakness except maybe Beilstein.” “Before I only used the internet, but I appreciate SciFinder more now at the end of the semester.” “The databases help you see info that is out there. It’s overwhelming! But, you can also see the unanswered questions. That was the most important part for me.”

10. THINGS FOR THE FUTURE • Drop Beilstein and focus on SciFinder and other databases / computer based tools? • $$ Issues with number of Scifinder seats. • Web of science, Online journals, etc.? • ChemDraw (nomenclature / NMR), molecular modeling? • Develop methods that would allow these exercises to be conducted In a large (≈ 250 person) lecture course. • Must modify goals for the non-majors audience • Improve the exit questionaire and develop an entrance questionaire that could be used to better quantify student progress. • Develop methods to have interaction between students as part of the online databases exercises. • Disseminate results if warranted.

11. ACKNOWLEDGEMENTS • My Chemistry 247 who cheerfully participated in the experiments described in this talk! • The Isaacs group for keeping the laboratory research rolling along. Funding NIH (GM61854) University of Maryland Research Corporation!!!