Beilstein Commander, SciFinder Scholar, and Google

Lyle IsaacsDepartment of Chemistry and Biochemistry

University of Maryland College Park

MY TEACHING PHILOSOPHY / GOALS

• Faculty members should act as seasoned guides to teach studentshow to ask their own scientific questions, how to answer them usingcurrent 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 thedisconnect 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 wasnon-existent.

• Given that I have room for only a couple of students in my laboratoryper semester, how can I engage the majority of students in “learningthrough research”?

• 2-minute essays• Group problem solving• Online databases as a powerful self-teaching tool.

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 regardingcucurbituril using SciFinder, Beilstein, and Google.• Devise a cocaine synthesis from commercially available materials.• Explore the generality of your favorite carbonyl condensationreaction from Ch. 23 of McMurry.

• Final Paper (100 points)• Must ask a scientific question and use either SciFinder or Beilsteinto answer that question.

SEARCHING WITH SCIFINDER

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?

A SELECTION OF STUDENT PAPER TOPICS(what happened to rock and roll?)

• Viagra: How is sildenafil synthesizedand how does it work?

• The action of pheromones in ahoney bee colony

• A Synthesis of Lysergic Acid

• Total Synthesis of (-)--Thujone

• The Drugs Behind Lethal Injection

• The Effects of Mustard Gas

• Synthesis of polyesters

• Chemical structure and synthesisof Silly Putty.

EtO

SN

N

N

HNN

N

O

O

O

Pr

Viagra

ClS

Cl

mustard gas

O

OO

O

O n

Polyethylene terephthalate(PET)

OCH3

H

(-)--thujone(in bsinthe)

NH

NH

O

O

S

Pentothl

OH

O O (From queen mndibulrpheromone)

GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS

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?

Google/Internet

Text / TAProf / Lib.

Yes Maybe No

70 17 13

SciFinderalone

73

3

27

9

0

21

0

68

SciFinder+ Internet

GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS

A B C D E60 33 5 261 33 28 648 38 1449 38 13 845 28 18 946 40 15 47 30 20 8 245 31 17 5 246 30 35 11 236 44 10 8 2

STRONGLYAGREE

STRONGLYDISAGREE

Q#12345678910

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.

A SELECTION OF STUDENT EVALUATION COMMENTS

• “The course gave me a better understanding of chemistry and allowedme to better relate it to everyday life.”

• “He asked questions of the class and allowed us to discuss them amongstourselves 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 hewould address at the beginning of the next class to be sure everyone gotthe concepts. I’ve found it very innovative and helpful.

• “There weren’t really any weakness except maybe Beilstein.” “Before Ionly used the internet, but I appreciate SciFinder more now at the end ofthe semester.” “The databases help you see info that is out there. It’soverwhelming! But, you can also see the unanswered questions. That wasthe most important part for me.”

THINGS FOR THE FUTURE

• Drop Beilstein and focus on SciFinder and other databases / computerbased 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 conductedIn a large (≈ 250 person) lecture course.

• Must modify goals for the non-majors audience

• Improve the exit questionaire and develop an entrance questionairethat could be used to better quantify student progress.

• Develop methods to have interaction between students as part of theonline databases exercises.

• Disseminate results if warranted.

• My Chemistry 247 who cheerfully participated in theexperiments described in this talk!

• The Isaacs group for keeping the laboratory research rolling along.

Funding

NIH (GM61854)University of Maryland

ACKNOWLEDGEMENTS