Stereochemistry Game: Creating and Playing a Fun Board Game To

Activity Cite This: J. Chem. Educ. XXXX, XXX, XXX−XXX

pubs.acs.org/jchemeduc

Stereochemistry Game: Creating and Playing a Fun Board Game To Engage Students in Reviewing Stereochemistry Concepts Jose ́ Nunes da Silva Júnior,* Daniel Esdras de Andrade Uchoa, Mary Anne Sousa Lima, and Andre ́ Jalles Monteiro Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, 60451-970 Fortaleza, Ceará, Brasil

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S Supporting Information *

ABSTRACT: A bilingual (English and Portuguese) innovative teaching method, Stereochemistry Game, is presented in the form of a board/card game to help students in their studies of stereochemistry. Four decks of cards (280 cards in total) and one board have been developed for second-year organic chemistry students in an effort to have them work together to solve stereochemistry problems in the context of a fun board game and to provide an efficient alternative to traditional methods of learning. This game encourages interaction and communication among students, develops strategic thinking, and requires minimal preparation and supervision from the professor. Based on the feedback of students and the assessment of learning, the game can be used as a complementary didactic tool by students for aiding them to review and to learn topics related to stereochemistry in a fun way.

KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Organic Chemistry, Humor/Puzzles/Games, Stereochemistry, Enrichment/Review Materials

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INTRODUCTION

There is a general agreement among educators that games have positive effects on achievement, problem-solving, perception, creativity, reasoning, interest, and engagement in task learning.11−17 Games are instrumental in the development of the mind and speed up the learning process, contribute to a more informal environment in the classroom by promoting more interaction between peers, and motivation to learn.18−26 Students process information better by taking part in games, and learn and understand concepts much easier. They engage their senses and are likely to have greater recall of what they have learned when participating in a game activity for learning.27 Specifically, regarding card games, studies have demonstrated that the teacher-made instructional card game and computer game are effective tools for the learning of chemistry concepts.28 In recent years, many educators have developed and incorporated games into their teaching to aid students to review and reinforce different chemistry topics, but only four of them have covered stereochemistry.29−41 Therefore, the development of an educational board game and its implementation in introductory organic chemistry courses can allow students to review stereochemistry topics in an entertaining way, facilitating their learning.

Stereochemistry is a branch of chemistry that deals with the spatial arrangement of atoms and groups in molecules and its relation to the properties and reactivities of the compounds. It also provides a basis for understanding the structure of chiral life-building blocks that appear in nature in enantiomerically pure substances, such as nucleotides, sugars, and α-amino acids.1 In this way, stereochemistry has been very important for the pharmaceutical and agrochemical industry, directly influencing the evolution of chiral licensing. The origin of this demand is intrinsically linked to the growing number of studies relating to biological properties with molecular chirality which affects how it interacts with other components of a cell.2−4 Thus, the mastery of stereochemistry is crucial for most areas of knowledge, making it a mandatory subject in all introductory disciplines of organic chemistry in many courses. Unfortunately, many students consider stereochemistry a subject difficult to grasp due to the student’s difficulty for three-dimensional visualization and understanding the concepts of asymmetric carbon and chirality. Indeed, teachers have reported learning difficulties of high school students and higher students in the field of stereochemistry since the 1940s.5−10 However, educators have recognized these difficulties and changed this paradigm by using different teaching strategies and developing educational games to engage and to enhance the students’ learning experience in interactive and enjoyable ways. © XXXX American Chemical Society and Division of Chemical Education, Inc.

Received: November 2, 2018 Revised: June 14, 2019

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DOI: 10.1021/acs.jchemed.8b00897 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

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MATERIALS

Decks of Cards, Board, and Dice

The Stereochemistry Game set is composed of one board (Figure 1), two dice (Figure 2), and four decks with 70 cards

Figure 1. Game board.

Figure 3. Examples of the four decks of cards.

the supervision of a professor who conducted the gaming process by motivating students to discuss each answer given by players and clarifying any students’ doubt when asked. Stereochemistry Game may be played with 2−5 players with procedures similar to those of many other board games. Initially, all players position their playing pieces on the initial position labeled “Start”. Afterward, a player throws the first die to define which deck he/she will flip a card to answer. When the player answers the question correctly, he or she must throw the second die, defining the number of spaces (1− 6) that their piece will advance in the track, and play then passes to the next opponent. However, there are 11 colored special spaces (blue, red, yellow, gray, and black) in the track. Blue spaces direct that the player must advance additional spaces in the track, while the red and black spaces direct that the player must back up some space or return directly to the start position, respectively. When the piece stops on a yellow space, the player must play again, but when the piece stops on a gray piece, the player misses a round. On the other hand, when the player responds incorrectly to a question, their piece does not move and play then passes to the next opponent. The game ends when a player reaches the final space labeled “Finish”. Each group of students received a key for checking the correct answers; the time spent on each match was 69 min on average. However, this average time can be lowered by reducing the number of players in the match.

Figure 2. Dice design.

each (Figure 3), which consist of questions covering the main topics of stereochemistry of organic compounds using these categories: • R or S: the player must define the absolute configuration of a tetrahedral stereogenic center (*) in a compound • Chiral or Achiral: the player must define whether a compound is chiral or achiral • They Are: the player must determine the relationship (same compound, constitutional isomers, enantiomers, or diastereomers) between two compounds • True or False: the player must classify a statement as true or false

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PLAYING THE GAME After a brief introduction covering the gameplay, students formed groups with five members for playing the game under B



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Figure 4. Comparison of students’ responses to statements about the Stereochemistry Game.

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• The dynamics of the game fits the age and developmental level of the players. • Students must not lose points for giving incorrect answers. • The game should be fun and promote greater interaction among students.

RESULTS AND DISCUSSION

Design and Implementation of the Game

Academic games are competitive exercises in which the objective is to win, and game actions are governed by rules of play and paraphernalia to execute the play, such as tokens, cards, and computer keys.42 Well-designed games are challenging and interesting for the players, while, at the same time, requiring the application of particular knowledge or skills. Players must apply subject matter or other relevant knowledge in an effort to advance in the exercise and win. Stereochemistry Game was designed for aiding students to review, to practice, and to refine their already-acquired knowledge of stereochemistry. The following criteria, which are related to playability, content, and usefulness, were used for designing Stereochemistry Game.

Content

The content of Stereochemistry Game aims to help students in reviewing stereochemistry concepts. Two fundamental imperatives were considered in determining the content of the game: (i) The questions should adequately cover the content seen in the classroom. (ii) the game should provide information relevant to the content; that is, it must show the student which aspects are most important for gaining knowledge, and it should address the subject under study. Usefulness

Playability

In designing Stereochemistry Game, these criteria were addressed: (i) The game should be an innovative didactic tool that would help students learn stereochemistry; (ii) the social nature of the game should allow students to learn in a cooperative environment; and (iii) the game should be a

These principles concerning playability were factored into the game design: • The game should be easy to play. C



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complementary didactic tool that would help students learn stereochemistry. Students’ Opinions

Students from three separate courses used Stereochemistry Game as supplementary didactic material after attending four consecutive lectures (2 h each) covering the content of stereochemistry. The 124 total first-year undergraduate students participated from either the Pharmacy 1 course (class 1, 25 students, in 2018), the Pharmacy 2 course (class 2, 22 students, in 2018), the Chemistry course (class 3, 23 students, 2018), the Pharmacy 3 course (class 4, 19 students, in 2019), or the Dentistry course (class 5, 35 students, in 2019). After the end of the activity, the professor invited all students to evaluate the game by completing a printed form containing nine statements with responses based on a Likerttype43 scale (Figure 4). All response results of each class are available separately in the Supporting Information. In general, the responses on the nine statements presented received a high level of agreement (agree plus agree totally) from those surveyed. Therefore, in general, Stereochemistry Game is easy to play, is fun, promotes interaction among the students, and allows students to learn in a cooperative environment. In addition, the game adequately covers the content seen in the classroom and can be used as a complementary didactic tool that helps students learn stereochemistry.

Figure 5. Percentage of students per grade interval of both classes.

performance of the students in class 1 compared with the students in class 3. After the test, the students of class 3 were also invited to play the game for 2 h and to evaluate the game by answering a similar printed test used by class 1. In addition, students were asked which of the two activities (game or problem solving) would be the most fun and which would contribute more to students’ learning. The students had three opinions as possible answers: game, problem solving, or they are similar. In class 3, 87% of the students considered that the use of Stereochemistry Game as an activity was more fun than the problem-solving activity. Regarding the instructional role, only 30.4% of the students considered that a problem-solving activity contributes to a better learning of the students than the use of the game, while 69.4% of the students considered both activities may contribute similarly to students’ learning. Therefore, Stereochemistry Game is a fun alternative method for reviewing and for contributing to the learning of the students. All students liked the implementation of Stereochemistry Game as suggested by the instructor. An important observation during the game related to the discussions that occurred with each answer. More important than the correct answers to the questions were students’ doubts and queries that arose with each question. In the students’ view, in addition to being a novel activity, the game led to greater interaction between classmates. Some students manifested their approval with positive statements such as the following: • “Excellent teaching tool that promotes learning and cooperation among students.” • “The game excelled at the role of breaking the standards, providing a more interactive environment capable of engaging even students less interested in chemistry.” • “The game escapes from the common strategy of the classes and, nevertheless, fulfills the objective of testing the knowledge and promoting the collaboration among classmates.” • “The game is amazing and we have learned a lot.” These statements indicate the importance given by the students to Stereochemistry Game as an instructional tool and the findings of the game in terms of the discussions and learning of the subjects proposed.

Instructional Role of the Game: Assessment of the Learning

Only classes 1 and 3 participated in this study because these students were taught by the same professor. The evaluation of performance of students from two classes, which were measured by comparing the means of the Academic Performance Index,44 revealed that there were no statistically significant differences (p = 0.858) between them. To validate Stereochemistry Game as a teaching tool, all students of classes 1 and 3 attended four consecutive traditional lectures (2 h each, with oral exposition and slideshow presentations) covering the stereochemistry contents. Class 1 was randomly chosen to play the game for 2 h, while class 3 participated in an in-class problem-solving activity for 2 h as well. In-class problem-solving activities allow students to tackle exercises during class with their peers and their instructor. Ideally, this genre of activity is used to increase the study time by solving exercises and to provide immediate feedback to students about misconceptions. Five days later, all students were evaluated through the same descriptive test which included questions at the cognitive levels that were developed in the game and the exercise lecture. The validation of the game was performed by comparing the scores obtained by both classes (Figure 5). Evaluating the performance in terms of a passing grade, that is, a mean score greater than or equal to 5.0, 84.6% of the students in class 1 obtained a score higher than 50% of the proposed objectives, compared with 69.7% of students in class 3. In addition, the percentage of students achieving greater than or equal to 71% of the objectives proposed was higher for class 1 in which the game was implemented than for class 3 in which the game was not implemented (42.3% and 39.5% for classes 1 and 3, respectively). Based on these results, the game is a teaching tool that may have contributed to the better D



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(13) Kim, B.; Park, H.; Baek, Y. Not Just Fun, But Serious Strategy: Using Meta-cognitive Strategies in Game-Based Learning. Comput. Educ. 2009, 52 (4), 800−810. (14) Tuzun, H.; Yilmaz-Soylu, M.; Karakus, T.; Inal, Y.; Kizilkaya, G. The Effects of Computer Games on Primary School Student’s Achievement and Motivation in Geography Learning. Comput. Educ. 2009, 52 (1), 68−77. (15) Wideman, H. H.; Owston, R. D.; Brown, C.; Kushniruk, A.; Ho, F.; Pitts, K. C. Unpacking the Potential of Educational Gaming: a New Tool for Gaming. Simul. Gaming 2007, 38 (1), 10−30. (16) Oyen, A.; Bebko, J. The Effects of Computer Games and Lesson Context on Children’s Mnemonics Strategies. J. Exp. Child Psychol. 1996, 62 (2), 173−189. (17) Robertson, J.; Howells, C. Computer Game Design: Opportunities for Successful Learning. Comput. Educ. 2008, 50 (2), 559−578. (18) Samide, M. J.; Wilson, A. M. Games, Games, Games; Playing to Engage with Chemistry Concepts. Chem. Educ. 2014, 19, 167−170. (19) Bannier, B. J. Motivating and Assisting Adult, Online Chemistry Students: A Review of the Literature. J. Sci. Educ. Technol. 2010, 19 (3), 215−236. (20) Westera, W.; Nadolski, R. J.; Hummel, H. G. K.; Wopereis, I. G. J. H. Serious Games for Higher Education: A Framework for Reducing Design Complexity. J. Comput. Assisted Learn. 2008, 24 (5), 420−432. (21) Stringfield, T. W.; Kramer, E. F. Benefits of a Game-Based Review Module in Chemistry Courses for Nonmajors. J. Chem. Educ. 2014, 91 (1), 56−58. (22) Dominguez, A.; Saenz-de-Navarrete, J.; de-Marcos, L.; Fernandez-Sanz, L.; Pages, C.; Martinez-Herraiz, J. J. Gamifying Learning Experiences: Practical Implications and Outcomes. Comput. Educ. 2013, 63, 380−392. (23) Parker, L. L.; Loudon, G. M. Case Study Using Online Homework in Undergraduate Organic Chemistry: Results and Student Attitudes. J. Chem. Educ. 2013, 90 (1), 37−44. (24) Spector, J. M. Emerging Educational Technologies: Tensions and Synergy. J. King Saud. Univ. Comp. Inf. Sci. 2014, 26 (1), 5−10. (25) Revell, K. D. A Comparison of the Usage of Tablet PC, Lecture Capture, and Online Homework in an Introductory Chemistry Course. J. Chem. Educ. 2014, 91 (1), 48−51. (26) Liberatore, M. W. Improved Student Achievement Using Personalized Online Homework. Chem. Eng. Educ. 2011, 45 (3), 184−190. (27) Boot, W. R.; Kramer, A. F.; Simons, D. J.; Fabiani, M.; Gratton, G. The Effects of Video Game Playing on Attention, Memory, and Executive Control. Acta Psychol. 2008, 129 (3), 387−398. (28) Rastegarpour, H.; Marashi, P. The Effect of Card Games and Computer Games on Learning of Chemistry Concepts. Procedia Soc.Behav. Sci. 2012, 31, 597−601. (29) Carney, J. M. Retrosynthetic Rummy: A Synthetic Organic Chemistry Card Game. J. Chem. Educ. 2015, 92 (2), 328−331. (30) Daubenfeld, T.; Zenker, D. A Game-Based Approach to an Entire Physical Chemistry Course. J. Chem. Educ. 2015, 92 (2), 269− 277. (31) Moreno, L. F.; Hincapie, G.; Alzate, M. V. Cheminoes: A Didatic Game to Learn Chemical Relationships Between Valence, Atomic Number, and Symbol. J. Chem. Educ. 2014, 91 (6), 872−875. (32) Martí-Centelles, V.; Rubio-Magnieto, J. ChemMend: A Card Game To Introduce and Explore the Periodic Table While Engaging Students’ Interest. J. Chem. Educ. 2014, 91 (6), 868−871. (33) Franco Mariscal, A. J.; Oliva Martínez, J. M. O.; Bernal Marquez, S. An Educational Card Game for Learning Families of Chemical Elements. J. Chem. Educ. 2012, 89 (8), 1044−1046. (34) Antunes, M.; Pacheco, M. A. R.; Giovanela, M. Design and Implementation of an Educational Game for Teaching Chemistry in Higher Education. J. Chem. Educ. 2012, 89 (4), 517−521. (35) Kavak, N. ChemPoker. J. Chem. Educ. 2012, 89 (4), 522−523. (36) Morris, T. A. Go Chemistry: A Card Game to Help Students Learn Chemical Formulas. J. Chem. Educ. 2011, 88 (10), 1397−1399.

CONCLUSIONS Stereochemistry Game is a beneficial learning tool to assist students to review stereochemistry in a fun and engaging way, and the social nature of the game allows students to learn in a cooperative environment. Futhermore, the game was wellreceived in evaluations by students, and based on the results obtained from the descriptive test, the game promotes the learning of stereochemistry and can be used as an alternative didactic tool to usual exercise solution classes.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.8b00897.

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Description of the Stereochemistry Game, including decks of cards, board, dice, and rules; survey statements and table with students’ survey results (PDF, DOCX) Artwork for all cards, board, keys, and dice in English and Portugese (ZIP)

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

José Nunes da Silva Júnior: 0000-0002-6631-4382 Notes

The authors declare no competing financial interest.

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REFERENCES

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Stereochemistry Game: Creating and Playing a Fun Board Game To

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