Fastest Fingers: A Molecule-Building Game for Teaching Organic

Activity pubs.acs.org/jchemeduc

Fastest Fingers: A Molecule-Building Game for Teaching Organic Chemistry Michael L. Eastwood* Richmond Secondary School, Richmond, British Columbia V6Y1Z3, Canada S Supporting Information *

ABSTRACT: Chemistry educators are constantly searching for new ways to engage their students in the classroom. Fastest Fingers is a team-based activity in which students race to solve an organic chemistry problem and then build the answer using a modeling kit. Points are awarded for speed as well as accuracy, encouraging teams to collaborate effectively and work efficiently. The game can be tailored to many different levels by varying the difficulty of the problem: topics such as nomenclature, isomerism, and basic reactions schemes can easily be included.

KEYWORDS: High School/Introductory Chemistry, First-Year Undergraduate/General, Organic Chemistry, Collaborative/Cooperative Learning, Hands-On Learning/Manipulatives, Humor/Puzzles/Games

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INTRODUCTION Organic chemistry is a notoriously difficult subject, especially for novice learners.1−3 The nomenclature is tedious, the molecules are difficult to visualize, reaction schemes can be complex, and mechanisms difficult to rationalize and apply.4 Previous authors in this Journal have explored ways to improve student engagement,5,6 and performance7−9 in chemistry. Instructors recognize that the social aspect of learning is vital;10,11 as a result, new activities and teaching strategies centered on student collaboration and cooperation are highly sought after. Games have long been heralded as an effective means to engage students and promote meaningful discussion of chemical concepts in the classroom.12 Educational games come in a variety of formats; recent publications in this Journal have outlined board games,13−15 card games,16−18 and game shows,19,20 among others. Myers’s Molecular Model Game makes use of modeling kits as teams of students race to build molecules with the correct VSEPR shape.21 Farmer’s Organic Chemistry Trivia22 and Schreck’s Organic Chemistry Squares23 are two games specifically designed to help students learn organic chemistry. This paper discusses a new “race-style” game called Fastest Fingers that requires students to work in teams to solve an organic chemistry problem and then build the correct molecule as quickly as possible. Fastest Fingers is best suited to classes of 20−40 students at either the high school or introductory college levels. An average game requires approximately 1 h; it can easily be adapted to a © XXXX American Chemical Society and Division of Chemical Education, Inc.

wide range of topics within organic chemistry and can be used for review or to further develop understanding of classroom concepts.

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MATERIALS The room should be arranged so that each team is located at a large table cleared of binders, books, backpacks, and other loose items. Four standard-size student desks pushed together makes an ideal workspace. To maximize efficiency, the clues should be prepared in advance by the instructor. Clues can be presented as individual PowerPoint slides or hand-written on an overhead projector screen, then revealed one at a time to begin each round. In low-tech classrooms, the instructor can either write clues on the board or simply read them aloud. Each team needs a ball-and-stick molecular model kit; see Table 1 for the minimum suggested quantities for each component in the kit. Each team is also permitted the use of a pencil and paper so that team members may do some planning and problem solving before actually building a molecule. If Fastest Fingers is being used as a review activity, it is recommended that no additional materials be allowed. If students are still developing their understanding of organic chemistry concepts (for example, in the middle of a unit), then items such as class notes, textbooks, and summary sheets can be made available at the instructor’s discretion.

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Table 1. Minimum Suggested Quantities for Each Component in the Molecular Model Kit

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Component

Typical Color

Quantity

Carbon atom Hydrogen atom Oxygen atom Nitrogen atom Halogen atom Single bond Multiple bond

Black White Red Blue Green  

15 40 10 5 5 50 10

GAME DESCRIPTION AND RULES Fastest Fingers is best suited to teams of three or four. If the game is played with teams larger than four, it is difficult to engage all students in each round. With teams of two, there is less interaction between students and the large number of teams can be overwhelming for the instructor (scoring involves recording which team finished first, second, etc.). Once students are seated with their teams, their first task is to assign each member a letter from A through D (for a team of four). Next, it is highly recommended that each team be asked to invent a team name; bonus points can be granted for organic chemistry-themed names (memorable examples include: “The Grignerds”, “Menzene”an all-male team, and “Cyclobutteam”a team of four, obviously). While not necessary, this is a good team-building activity and helps stimulate competition early on as students strive to “out-pun” each other. The students should be briefed on the following rules before the game begins: 1. Each round, the instructor will reveal a clue on the screen. The goal is to be the first team to correctly build the organic molecule associated with this clue. 2. Only certain players are allowed to be builders (i.e., handle the model kit components) in each round. The other players may assist the builders by drawing structures on paper or providing verbal instructions; however, they may not touch the model kit. 3. Once a team has built the target molecule, all members must raise their hands to indicate to the instructor that building is complete. There can be no further changes to a molecule once a team has raised their hands. 4. The first team to submit an answer receives 5 speed points, second receives 4 speed points, third receives 3 speed points, and so on. 5. Correct answers receive 5 molecule points. Points will be deducted for errors. 6. Teams must completely disassemble their molecule from one round before proceeding to the next round.

Figure 1. Sample slides showing: (A) “pre-clue” slide identifying the builders; (B) nomenclature clue; (C) isomerism clue; (D) simple reaction scheme clue.

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TIPS FOR THE INSTRUCTOR Each round lasts 4−8 min, depending on the difficulty of the problem. Typically, 10 rounds can be completed in a 1-h period. Figure 1 illustrates some sample clues, and a short video demonstration of the game is available on YouTube.24 Other helpful tips to ensure that the game runs smoothly are outlined below. 1. Before each round begins, check that each team has completely disassembled the molecule from the previous round. Crafty students may try to “carry over” a methyl group (or more!) to the next round to speed up the building process. Also, once a clue has been revealed and

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B

students are busy discussing and building the target molecule, it is a good idea to circulate the room and check that only the builders are handling the model kit. Teams can gain a significant advantage if additional students assist with the building. Threatening to penalize teams for these practices (or other forms of cheating) is an effective way to ensure that everyone follows the rules. Clearly post or announce the identities of the builders before revealing each round’s clue (see Figure 1A). If the game is being played in teams of four, two is a standard number of builders. However, it is a good idea to change this number occasionally, with some rounds involving a lone builder and others involving three or more. In another variation, the instructor also specifies a recorder: the only player who can use pencil and paper. This definition of an additional role makes the game a little more dynamic by adding some variety to the individual tasks. To help with the scoring, draw a map of the classroom with the locations of each team clearly marked. As each team indicates they are finished, write the number of speed points they earned beside their location on the map. Using this technique makes it easier to keep track of the speed points, as it is easy to forget the exact order in which teams finished once a round is complete. Also, watch out for teams that prematurely announce they are finished (to earn more speed points) and then hastily add atoms or make changes when nobody is looking. Point deductions for errors in the target molecule should vary depending on the severity of the error. For minor errors such as forgetting a hydrogen atom, a single point is a suitable penalty. More serious errors such as an incorrect number of carbon atoms or the wrong functional group should carry substantial penalties, or not be awarded any points at all. Ultimately, instructors can adjust these penalties according to their own preferences and the knowledge level of their students. The number of points awarded for speed or accuracy can be adjusted up or down according to the number of teams participating or the instructor’s desire to emphasize one over the other. dx.doi.org/10.1021/ed3004462 | J. Chem. Educ. XXXX, XXX, XXX−XXX

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BENEFITS OF USING FASTEST FINGERS IN THE CLASSROOM Fastest Fingers is an effective tool for engaging students in organic chemistry problem solving. The game can easily be incorporated into the middle of a unit to develop student understanding (formative) or used to assess knowledge and skills as a review activity (summative). After being presented with a problem, students must first work together to solve it and then collaborate effectively to build the object molecule. Students assume different roles in different rounds, adding a dynamic element to the game. In the author’s high school classes, the vast majority of students reported that they enjoyed the activity and many felt that the problem-solving skills they developed helped deepen their understanding of organic chemistry. A common complaint of chemistry teachers is that students fail to appreciate the three-dimensional nature of organic molecules; the ability to visualize these molecules is essential for understanding organic chemistry.25,26 Lewis structures for these molecules can lead students to the misconception that they are two-dimensional, with all bond angles equal to either 90° or 180° (Figure 2). Models are central to science learning,

different goals. At the beginning or middle of a unit, it is effective in getting students to practice applying the principles they are currently learning and to learn from their mistakes. Near the end of a unit, the game is a meaningful way for students to check their overall mastery of core concepts.

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ASSOCIATED CONTENT

S Supporting Information *

A demonstration video and sample games from a range of organic chemistry topics. This material is available via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS I would like to thank Jackie Stewart and Andrew Tovey for their valuable feedback during the writing process. I would also like to thank former JCE associate editor Erica Jacobson, whose article “Become a Journal of Chemical Education Author”29 ultimately inspired me to start writing. Finally, a big thank-you to all my chemistry students, past and present, who participated so enthusiastically in our epic Fastest Fingers battles!

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REFERENCES

(1) Mullins, J. J. J. Chem. Educ. 2008, 85, 83−87. (2) Green, G.; Rollnick, M. J. Chem. Educ. 2006, 83, 1376−1381. (3) Pungente, M. D.; Badger, R. A. J. Chem. Educ. 2003, 80, 779−784. (4) Teixeira, J.; Holman, R. W. J. Chem. Educ. 2008, 85, 88−89. (5) Bunce, D. M.; Flens, E. A.; Neiles, K. Y. J. Chem. Educ. 2010, 87, 1438−1433. (6) Shaver, M. P. J. Chem. Educ. 2010, 87, 1320−1323. (7) Szu, E.; Nandagopal, K.; Shavelson, R. J.; Lopez, E. J.; Penn, J. H.; Scharberg, M.; Hill, G. W. J. Chem. Educ. 2011, 88, 1238−1242. (8) Bunce, D. M.; VandenPlas, J. R.; Soulis, C. J. Chem. Educ. 2011, 88, 1231−1237. (9) Wamser, C. C. J. Chem. Educ. 2006, 83, 1562−1566. (10) Bruffee, K. A. Collaborative Learning; Johns Hopkins University Press: Baltimore, MD, 1993. (11) Johnson, D. W.; Johnson, R. T.; Smith, K. A. Active Learning: Cooperation in the College Classroom; Interaction Book Company: Edina, MN, 1991. (12) Russell, J. V. J. Chem. Educ. 1999, 76, 481−484. (13) Antunes, M.; Pacheco, M. A. R.; Giovanela, M. J. Chem. Educ. 2012, 89, 517−521. (14) Pippins, T.; Anderson, C. M.; Poindexter, E. F.; Whitney Sultemeier, S.; Schultz, L. D. J. Chem. Educ. 2011, 88, 1112−1115. (15) Mosher, M. D.; Mosher, M. W.; Garoutte, M. P. J. Chem. Educ. 2012, 89, 646−648. (16) Costa, M. J. J. Chem. Educ. 2007, 84, 977−978. (17) Morris, T. A. J. Chem. Educ. 2011, 88, 1397−1399. (18) Sevcik, R. S.; Hicks, O.; Schultz, L. D. J. Chem. Educ. 2008, 85, 514−515. (19) Clark, T. M. J. Chem. Educ. 2011, 88, 428−431. (20) Campbell, S. J. Chem. Educ. 2002, 79, 458. (21) Myers, S. A. J. Chem. Educ. 2003, 80, 423−424. (22) Farmer, S. C. J. Chem. Educ. 2011, 88, 1648−1650. (23) Schreck, J. O. J. Chem. Educ. 1992, 69, 233−234. (24) Eastwood, M. L. Fastest FingersA Molecule Building Game [video file]. http://www.youtube.com/watch?v=vVTy1clF0TA (accessed May 2013). (25) Small, M. Y.; Morton, M. E. J. Coll. Sci. Teach. 1983, 13, 41−43.

Figure 2. Comparing the Lewis structure and ball-and-stick representation of acetic acid.

and chemistry in particular.27,28 In Fastest Fingers, students go beyond just looking at models of organic molecules: they are required to build the molecules themselves. Through this process, students gain a better understanding of the threedimensional shape of these molecules. In many academic games, especially those where speed is a factor, the students with the quickest minds or strongest knowledge base dominate the play. Those who take more time to problem solve or are still developing their understanding of a topic are often limited in their participation. In Fastest Fingers, rapid construction of the molecule requires planning and collaboration among teammates: efficiency is rewarded. Because roles are constantly changing, a team’s success will depend most strongly on the ability of its members to communicate and work together effectively, not on the abilities of any individual member. This unique feature of the game makes it an excellent tool for instructors who strive to get participation from a larger percentage of their class. Every student, regardless of ability, has a legitimate opportunity to make a real contribution to his or her team’s success and feel the pride that comes with doing so. Fastest Fingers is easily adaptable to different levels of organic chemistry. For introductory courses, the clues can be constructed to cover topics in nomenclature and isomerism. For more advanced courses, the clues can involve reaction schemes that require players to determine a reactant or product molecule before building it. The activity can also be implemented at different stages of instruction to achieve C

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(26) Shaw, P. N.; Hyde, R. T.; Jackson, D. E.; Woods, K. J. Chem. Educ. 1995, 72, 699−702. (27) Criswell, B. J. Chem. Educ. 2011, 88, 415−419. (28) Gilbert, S. J. Res. Sci. Teach. 1991, 28, 73. (29) Jacobsen, E. K. J. Chem. Educ. 2012, 89, 2−3.

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