Wikipedia 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, the page “Tryptamine”(7) displayed a chemical structural error in a reaction scheme(8) since 2011.(9) Inspection of the original reference(10) confirms that a copy-and-paste mistake took place.

Figure 1 Figure 1. Incorrect scheme reproduced from the “Pfitzner–Moffatt oxidation” Wikipedia page,(3) as seen on June 2016.

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.

The author declares no competing financial interest. Acknowledgment ARTICLE SECTIONS Jump To 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. References ARTICLE SECTIONS Jump To This article references 13 other publications. 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 DOI: 10.1021/ed100017k 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 DOI: 10.1021/acs.jchemed.5b00525 3 Wikipedia contributors . Pfitzner-Moffatt oxidation . 2016 ) . https://en.wikipedia.org/wiki/Pfitzner%E2%80%93Moffatt_oxidation (accessed 27 Jun 4 Wikipedia contributors . Pfitzner–Moffatt oxidation: Revision history . 2016 ) . https://en.wikipedia.org/w/index.php?title=Pfitzner%E2%80%93Moffatt_oxidation&action=history (accessed 28 Jun 5 Wikipedia contributors . Novobiocin . 2016 ) . https://en.wikipedia.org/wiki/Novobiocin (accessed 28 Jun 6 Wikipedia contributors . Novobiocin: Revision history . 2016 ) . https://en.wikipedia.org/w/index.php?title=Novobiocin&action=history (accessed 27 Jun 7 Wikipedia contributors . Tryptamine . 2016 ) . https://en.wikipedia.org/wiki/Tryptamine (accessed 28 Jun 8 The indole intermediate in the Abramovitch–Shapiro reaction is incorrectly represented as an indoline. 9 Wikipedia contributors . Tryptamine: Revision history . 2016 ) . https://en.wikipedia.org/w/index.php?title=Tryptamine&action=history (accessed 28 Jun 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 DOI: 10.1039/JR9560004589 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 DOI: 10.1021/acs.jchemed.5b00523 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 DOI: 10.1021/ed100367v 13 Brooks, D. W. ; Markwell, J. Evaluating Web-Based Information: Access and Accuracy J. Chem. Educ. 2008 , 85 , 458 – 459 DOI: 10.1021/ed085p458

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