In the Classroom
Where's Ester? A Game That Seeks the Structures Hiding Behind the Trivial Names Marcus Angelin* and Olof Ramstro. m Department of Chemistry, The Royal Institute of Technology, Teknikringen 30, S-10044, Stockholm, Sweden *
[email protected] During the mid-19th century, there was a large expansion in the field of organic chemistry. As chemical science and technology became more sophisticated, a greater understanding of the structures of organic compounds was developed. This progress founded a need for a systematic nomenclature. The first step toward standardization was taken by the national chemical societies at an international conference in Geneva 1892, but the process was disrupted by World War I (1). Later, the standardization was passed to the International Union of Pure and Applied Chemistry (IUPAC), which continue to be responsible for organic, inorganic, and biochemical nomenclature to this day (2). Even though all organic compounds can be named systematically using the IUPAC nomenclature, many of the compounds use the nonsystematic names, referred to as their “trivial names”. These names often originate from chemical history or from the natural sources of specific compounds. They normally have no relationship to each other or to the actual structure, but often need to be memorized by the students owing to their frequent use in chemical language and literature. This is in most cases accomplished by classic “plug-and-chug” exercises. Games and puzzles are great assets for educators to provide variability and a “touch of fun” to the often quite strict curricula. There is a range of more recent examples, as well as summarizing articles featured in earlier issues of this Journal (3). In this article, we present “Where's Ester?”, a game that helps students learn the trivial names of many essential organic compounds. It also includes expansions for learning the amino acids, as well as the generic name and structure of the 24 most-sold pharmaceuticals (4). The game is based on the board game “Guess Who?”, in which two players are challenged to correctly guess which game character the other player has drawn randomly from a deck including all 24 game characters (5). Each player has a board displaying all characters and is allowed to alternately ask “yes-or-no” questions regarding the characters facial features to narrow down the possibilities or to make a direct guess. The first player that correctly guesses the other players character wins the game. In “Where's Ester?” an analogous process is used to find the correct structure and trivial name for a range of chemical compounds. Game Preparations Three copies of the selected 24-compound card chart of structures and trivial names need to be printed and cut into individual cards.1 One complete set is shuffled and put as a deck facedown on the table. The other two are spread out faceup in 406
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front of each player (Figure 1). The players' view of each other's card chart is blocked by a protective screen (anything could be used). Playing the Game Both players randomly pick a card from the facedown deck and a coin toss decides who starts the game.2 The selected player (player 1) has the option either to directly make a guess to which compound player 2 has drawn or to ask a “yes-or-no” question regarding its structure. At this point in the game, the chance of guessing correctly is low (1 out of 23). The smarter option is to ask a general question such as “Does your compound have any rings?”. Player 2 may answer the question “Yes!”, and player 1 can eliminate all structures that do not match the answer. The turn is now passed to player 2. This process of questioning, answering, and guessing continues until one player has guessed the correct compound. Then, the deck is shuffled and the game can start over again. Discussion The game was first tested within the department to ensure that it was fun, balanced, and aided learning. Generally, it was greatly appreciated by both students and instructors. Besides the fact that it forced everyone to work with the structures and trivial names, it also required some thinking to come up with a good question for a particular scenario. It made the players see structural similarities among compounds that they might not have seen in a normal case. This activity can enhance the learning process into something more than just memorization. The chart with pharmaceuticals interested many of the students and instructors because there is often a lack of knowledge when it comes to the structures of top-selling pharmaceuticals. In this case, the game not only provided this knowledge, but also linked the particular pharmaceutical to the targeted symptom and to a certain extent, also to the complex nature of naming pharmaceutical products (6). Next, the game was tested on a smaller scale among firstyear undergraduate chemistry students. During their introductory course in organic chemistry, the students need to learn the structures and trivial names of the compounds supplied in this article. The testing was made during laboratory sessions in which students had the opportunity to try the game while they were waiting for their reactions to finish. This was very popular and was experienced as a productive break
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Vol. 87 No. 4 April 2010 pubs.acs.org/jchemeduc r 2010 American Chemical Society and Division of Chemical Education, Inc. 10.1021/ed800129r Published on Web 03/09/2010
In the Classroom
Figure 1. A reduced version of the “Where's Ester?” game setup. The black line represents a barrier between the two players.
3. For updates on “Where's Ester” and other projects, see Marcus Angelin's homepage, http://www.marcusangelin.com (accessed Jan 2010).
from a generally demanding laboratory session. Most of all, it helped the students to learn required material in a fun and social setting. Conclusion
Literature Cited
Overall, “Where's Ester?” provided the students with a fun and intriguing way to learn a range of chemical structures and their trivial names. The dynamics of the game allows the students to constantly think about the structures and their mutual similarities. This is something that is important to increase the understanding beyond memorization and may be of help when working with more complex structural relationships in the future. The possibility of varying and expanding the game by using different sets of card charts also makes the game suitable for students at different stages of their academic studies. In this article, three unique charts are supplied: general organic compounds, amino acids, and top-selling pharmaceuticals. However, we plan to extend the scope of this game by publishing more of these card charts on the Web.3
1. Societe Chimique de France. Bull. Soc. Chim. 3, 1892, 7, xiii. 2. International Union of Pure and Applied Chemistry (IUPAC). http://www.iupac.org (accessed Jan 2010). 3. (a) Samide, M. J. J. Chem. Educ. 2008, 85, 1512–1514. (b) Sevcik, R. S.; Hicks, O.; Schultz, L. D.; Alexander, S. V. J. Chem. Educ. 2008, 85, 514–515. (c) Sevcik, R. S.; Hicks, O.; Schultz, L. D.; Alexander, S. V. J. Chem. Educ. 2008, 85, 516–517. (d) Capps, K. J. Chem. Educ. 2008, 85, 518. (e) JCE Resources. J. Chem. Educ. 2008, 85, Web1. (f) Russell, J. J. Chem. Educ. 1999, 76, 481–484. 4. Top 200 drugs for 2007 by sales (source: Verispan VONA). http:// www.drugs.com/top200.html (accessed Jan 2010). 5. “Guess Who?” Board game invented by Theora Design, manufactured by Milton Bradley. http://www.theoradesign.com (accessed Jan 2010). http://www.hasbro.com (accessed Jan 2010). 6. Gantner, F.; Schweiger, C.; Schlander, M. Drug Inf. J. 2002, 36, 807– 824.
Notes 1. Necessary materials are supplied in the supporting information. 2. Card sizes are made to fit in a standard “Guess Who?” board game. A complete graphic game demonstration is supplied in the supporting information.
r 2010 American Chemical Society and Division of Chemical Education, Inc.
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Supporting Information Available Card charts for the organic compounds, amino acids, and topselling drugs; pictures of the game setup. This material is available via the Internet at http://pubs.acs.org.
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