Letter pubs.acs.org/jchemeduc
Glaring Chemical Errors Persist for Years on Wikipedia Michael D. Mandler* Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States ABSTRACT: This letter is a response to an article (J. Chem. Educ. 2011, 88, 769−771) about incorporating Wikipedia into the undergraduate chemistry curriculum. Though Wikipedia does not require the vetting of submitted material, it is undoubtedly a major resource for the 21st century chemist. Unfortunately, many errors in chemical structure are present in Wikipedia chemistry articles. Even when these mistakes are discovered and reported, articles are sometimes subsequently left uncorrected. In order to be a more useful resource, particularly for undergraduate learning, Wikipedia depends on timely factchecking and editing by the chemical community. KEYWORDS: General Public, High School/Introductory Chemistry, First-Year Undergraduate/General, Chemoinformatics, Misconceptions/Discrepant Events, Learning Theories, Descriptive Chemistry, Internet/Web-Based Learning, Collaborative/Cooperative Learning
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ikipedia chemistry articles are widely used by students from K−12 to the graduate school level. As a result, many teachers have begun to incorporate Wikipedia into the chemistry curriculum; this letter responds to an article on this topic from this Journal.1 In one example, first-year college chemistry students were provided a set of Wikipedia articles and asked to read them for accuracy and completeness. Later they could correct any mistakes or add pertinent information. Alternatively, students could create an entirely new article if a previous one did not exist. Overall, the students responded very positively to the assignment; both they and the teachers agreed that Wikipedia, if used correctly, can be a great source of chemical information. Wikipedia is an excellent source for the initial retrieval of chemical information and primary references, but articles should also be carefully scrutinized and cross-checked with the peer-reviewed literature. Chemistry infoboxes are an especially useful tool for looking up chemical data, and their information can be usually trusted if a green checkmark is present.2 Unfortunately, there is no “green checkmark” for every chemistry article on Wikipedia, and errors are not necessarily rapidly fixed by community editors. After surfing the “Organic Reactions” pages, I found several mistakes, most of which were structural. Below, I select three examples of these errors that were glaringly visible to the public, but were not corrected until I found them. Since 2010, the Wikipedia page “Pfitzner−Moffatt oxidation”3 included an erroneous figure depicting an alkoxysulfonium ylide with two adjacent positive charges (Figure 1).4 Second, the Wikipedia page “Novobiocin”,5 a well-known antibiotic and natural product, contained figures of biosynthetic pathways with many structural errors. These errors had been on the page since 2012.6 Ironically, there was a note warning: “Image contains multiple errors in chemical structure.” Third, © XXXX American Chemical Society and Division of Chemical Education, Inc.
Figure 1. Incorrect scheme reproduced from the “Pfitzner−Moffatt oxidation” Wikipedia page,3 as seen on June 2016.
the page “Tryptamine”7 displayed a chemical structural error in a reaction scheme8 since 2011.9 Inspection of the original reference10 confirms that a copy-and-paste mistake took place. In theory, Wikipedia chemistry articles should be vetted for accuracy in a timely fashion. In reality, this is not the case. Major chemical errors on Wikipedia persist for years, sometimes even after they have been reported. Instructors emphasize the need to edit Wikipedia chemistry articles, since they are such an important source.1,11−13 The chemistry community as a whole (industry, government, and academia) needs to follow suit. The peer-reviewed literature should remain as the paramount source for the retrieval of trustworthy information, but Wikipedia chemistry articles should be checked and edited to mirror the literature. If more chemists became Wikipedia editors, fewer mistakes would be transmitted to students and the general public.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Received: June 28, 2016 Revised: September 29, 2016
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DOI: 10.1021/acs.jchemed.6b00478 J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Letter
Notes
The author declares no competing financial interest.
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ACKNOWLEDGMENTS The author gratefully acknowledges Lee A. Friedman (University of Maryland, College Park) for proofreading the manuscript, discovering several Wikipedia mistakes, and helping to correct them. Hannah M. Lebovics (University of Maryland, College Park), Joseph S. Wzorek, Rebecca J. Taylor, David C. Tomasek, and James Lee (Harvard University) are acknowledged for their help putting together the manuscript.
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REFERENCES
(1) Martineau, E.; Boisvert, L. Using Wikipedia To Develop Students’ Critical Analysis Skills in the Undergraduate Chemistry Curriculum. J. Chem. Educ. 2011, 88, 769−771. (2) Walker, M. A.; Li, Y. Improving Information Literacy Skills through Learning To Use and Edit Wikipedia: A Chemistry Perspective. J. Chem. Educ. 2016, 93, 509−515. (3) Wikipedia contributors. Pfitzner-Moffatt oxidation. https://en. wikipedia.org/wiki/Pfitzner%E2%80%93Moffatt_oxidation (accessed 27 Jun 2016). (4) Wikipedia contributors. Pfitzner−Moffatt oxidation: Revision history. https://en.wikipedia.org/w/index.php?title= Pfitzner%E2%80%93Moffatt_oxidation&action=history (accessed 28 Jun 2016). (5) Wikipedia contributors. Novobiocin. https://en.wikipedia.org/ wiki/Novobiocin (accessed 28 Jun 2016). (6) Wikipedia contributors. Novobiocin: Revision history. https://en. wikipedia.org/w/index.php?title=Novobiocin&action=history (accessed 27 Jun 2016). (7) Wikipedia contributors. Tryptamine. https://en.wikipedia.org/ wiki/Tryptamine (accessed 28 Jun 2016). (8) The indole intermediate in the Abramovitch−Shapiro reaction is incorrectly represented as an indoline. (9) Wikipedia contributors. Tryptamine: Revision history. https://en. wikipedia.org/w/index.php?title=Tryptamine&action=history (accessed 28 Jun 2016). (10) Abramovitch, R. A.; Shapiro, D. Tryptamines, Carbolines, and Related Compounds. 2. A Convenient Synthesis of Tryptamines and Beta-Carbolines. J. Chem. Soc. 1956, 0, 4589−4592. (11) Shultz, G. V.; Li, Y. Student Development of Information Literacy Skills during Problem-Based Organic Chemistry Laboratory Experiments. J. Chem. Educ. 2016, 93, 413−422. (12) Moy, C. L.; Locke, J. R.; Coppola, B. P.; McNeil, A. J. Improving Science Education and Understanding through Editing Wikipedia. J. Chem. Educ. 2010, 87, 1159−1162. (13) Brooks, D. W.; Markwell, J. Evaluating Web-Based Information: Access and Accuracy. J. Chem. Educ. 2008, 85, 458−459.
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DOI: 10.1021/acs.jchemed.6b00478 J. Chem. Educ. XXXX, XXX, XXX−XXX
