Activity pubs.acs.org/jchemeduc
Analogue Three-Dimensional Memory Game for Teaching Reflection, Symmetry, and Chirality to High School Students Daniel de Melo Silva and Carlos Magno Rocha Ribeiro* Programa de Pós-Graduaçaõ em Ensino de Ciências da Natureza, Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Campus Valonguinho, Niterói, RJ 24020-150, Brazil S Supporting Information *
ABSTRACT: This interdisciplinary analogue 3D Memory Game is a version of a card-based memory game, developed to encourage high school students to use deductive reasoning skills and to understand reflection (mirror images), symmetry, and chirality. Instead of cards, three-dimensional pieces are used in order to facilitate the understanding of the spatial arrangement of things, both geometric objects and organic compounds. Correlating geometric objects with the simple molecular model representation of organic compounds, the game promotes knowledge transposition to spatial recognition of chemical structures and chirality in formal education, classrooms, or nonformal educational settings (e.g., a science center or discovery center or university outreach setting). The game was used in 2016 in a classroom with 16 students in a high school in São Gonçalo, Rio de Janeiro, Brazil, as well as at a science fair in 2015. The game lasts 15−25 min when played by 5 or 3 groups of 2 students, respectively. On the basis of the feedback of students and teachers, the game was considered interesting, and the students were motivated to participate more actively in the classroom. Learning about these concepts by the students was significant. KEYWORDS: High School/Introductory Chemistry, Interdisciplinary/Multidisciplinary, Hands-On Learning/Manipulatives, Chirality/Optical Activity, Learning Theories
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INTRODUCTION The word “chiral” was possibly used initially by Lord Kelvin in 18831 at a Robert Boyle Lecture; chiral derives from the Greek word kheir, meaning “hand”. Chirality is considered to be a property of objects and figures and it is a topic discussed in various disciplines. Thus, the term “handedness” is commonly used as a synonym for chirality.2 For a definition or discussion of chirality, the correlation between an object and its image in a plane mirror is often used. Thus, it is important to have a notion of the reflection concept. An object is chiral if it and its mirror image do not coincide by any ideally realized series of rigid motions. Then, in general, the persons need to have a sense of how the things are arranged in space to understand and correlate the symmetry/asymmetry of things with achirality/chirality. The concept of asymmetry was used for the first time in chemistry by van’t Hoff and Le Bel in 1874 when considering the work of Louis Pasteur regarding the resolution of a mixture of tartaric acid salt isomers developed between 1848 and 1853. In his work, Pasteur recognized that two of the isomers polarized light differently (one to the left and the other to the right) and that this must be due to an asymmetric grouping of atoms in optically active molecules.3 Discussion of the use of these terms (chirality and asymmetry)2−4 demonstrates the importance and interdisciplinary nature of this area of knowledge; the chirality of a © XXXX American Chemical Society and Division of Chemical Education, Inc.
substance is a property of molecules and is part of the curriculum of higher education in which stereochemistry is discussed.5 To address the teaching and learning of the concepts of asymmetry and chirality, several educational studies have been published that underscore the importance of chirality and of recognition of chirality in chemicals compounds, as well as the improvement of students’ ability in spatial recognition of objects.6−14 An analogue or digital game can be an important educational tool to motivate students and facilitate the teaching and learning process in several areas of knowledge.15−18 Using a problematization19 approach is a pedagogical methodology for developing students’ critical and reflective processes and making them the agents of their own intellectual development. The use of the game and problematization were regarded as the pedagogical approach of this study that aimed to use pairs of three-dimensional figures to discuss the chirality based in the reflection (mirror image of the pieces) and symmetry or asymmetry (overlap of the object and its mirror image). We also used this approach to make a transposition of knowledge using three-dimensional models that represent organic Received: March 23, 2017 Revised: June 26, 2017
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DOI: 10.1021/acs.jchemed.7b00219 J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
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molecules that were similar to certain geometric objects used in this 3D Memory Game.
that player wins the two pieces and removes them from the game. The game ends when all the pieces are uncovered and no more matches can be made. The winner is the player or team possessing the most objects (Figure 2).
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THE GAME This analogue 3D Memory Game is a version of a memory cards game, also known as concentration, match match, shinkeisuijaku, pexeso, or simply pairs.20,21 In this type of game the cards are placed with the images face down on any type of surface that later must be turned two by two, and the player wins the game if he make the largest number of pairs. It is only necessary to remember the cards with the figures that form the pairs. The 3D Memory game consists of pairs of symmetric and asymmetric pieces that are mirror images of each other (superimposable or nonsuperimposable, respectively), as well as wooden boxes in which these pieces are placed (Figure 1). It
Figure 2. Summary of the game rules.
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HAZARDS No parts of the game are dangerous, since they have been chosen or constructed without pointed and toxic materials. They should not be made of glass or be so small that they may be swallowed. (See the Supporting Information for more details.)
Figure 1. Three-dimensional Memory Game with the pairs of pieces.
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PLAYING THE GAME The 3D Memory Game has been played by 16 students in 8 groups of an introductory chemistry class from a third year of a high school in São Gonçalo, Rio de Janeiro, Brazil, in 2016. A simple 30 min discussion on reflection (mirror image), symmetry, and chirality (as well as relevant physical, mathematics, and chemistry concepts, respectively) was initially conducted before the students started the game. (See the instructor’s notes in the Supporting Information.) After this, students were informed about the game rules for 15 min, and a trial of the game was played in which it was determined that, relative to the problematization, students could successfully answer the following question: “Are the objects chiral or achiral?” Next, the students began playing the 3D Memory Game (Figure 3). (See the student handout in the Supporting Information.) Two rounds were played, one with 5 groups of 2 students and the other with 3 groups of 2 students. Each round was played for about 25 and 15 min, respectively, until one group won. The game was also used in the National Week of Science and Technology of Federal Fluminense University between 12 and 19 October 2015 as a science exploration for approximately 50 public school students and general visitors of Niterói, Rio de Janeiro, Brazil.
is necessary to remember where the pairs of pieces are placed, but the players also need to know if the pieces are chiral or not chiral. The three-dimensional pieces are everyday objects, such as toy animals, geometric objects, and simple molecular models representing organic compounds. Game Rules
After the teacher sets up the game so that all the pieces are carefully positioned and randomly distributed, and then covered with inverted boxes or paper bags, play can begin. (See the Supporting Information for further details.) 1. A player (or team) uncovers two objects and observes whether the two pieces are mirror images of each other. If the player answers that the objects are not mirror images of each other, the pieces are covered and another player takes a turn. If the player answers that the two pieces are mirror images of each other, this is checked. If the answer is wrong, the pieces are covered and another player or team takes a turn. However, if the player answers correctly, play continues to the next question, in step 2. 2. If a player or team has correctly identified a match of two pieces that are mirror images of each other (step 1), the player must next answer a question of whether the pieces are symmetrical or asymmetrical. If the answer is wrong, the pieces are covered, and another player or team takes a turn. However, if the player answers correctly, play continues to the next question, in step 3. 3. At this last step, the player must answer a question of whether the objects are chiral or achiral. If the answer is wrong, the pieces are covered and another player or team takes a turn. However, if the player answers correctly,
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RESULTS AND DISCUSSION Before instruction, students answer a diagnostic questionnaire of 6 questions to determine their prior knowledge. Four questions address the topics of reflection, symmetry, and chirality; one question asks whether the students had ever used B
DOI: 10.1021/acs.jchemed.7b00219 J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Activity
This approach was proposed to develop students’ reflective and critical thinking abilities in solving problems. Students were able to finish the game in an appropriate time, showing that they were able to recognize the chirality of objects through problematization and playful pedagogical methodology, using this 3D Memory Game. In general, students and visitors to the science fair were able to correlate the objects with their respective properties of mirror image, symmetry, and chirality, indicating comprehension of the game rules and concepts involved to play successfully.
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ASSOCIATED CONTENT
S Supporting Information *
Figure 3. Students playing the game.
The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.7b00219. Additional game details presented as a student handout and instructor’s notes (PDF, DOC)
games for learning, and one question asks whether the students had ever played a memory card game (a “2D” version). The results observed from these 16 students in 2016 can be synopsized as follows: • These students had a good knowledge of reflection and symmetry, 62% and 58%, respectively. • These students had no knowledge about chirality. • Of these students, 61% had never used games for learning. • Of these students, 74% had knowledge of the memory “2D” game, but only 35% had played this type of game for learning purposes. After instruction about chirality and several rounds of 3D Memory Game play, an evaluative questionnaire was administered to gauge the contribution of the game to students’ learning, as well as the students’ opinions about the 3D Memory Game. Four questions addressed the concepts, and two questions asked for the students’ opinions of the game. From the students’ answers, it is possible to conclude the findings below: • These students showed a very small improvement in knowledge of reflection and symmetry, with gains of 6% and 4% (from 62% to 68%, and 58% to 62%), respectively. • Considering the time spent playing the game and the correct answers students gave, it seems likely that learning the concepts of reflection, symmetry, and specifically chirality can be helped by playing the 3D Memory Game. • Of these students, 100% considered the game interesting and felt more motivated to actively participate during instruction; they thought the time for playing the game was adequate, and they thought they were helped to better understand the concept of chirality. Four teachers from the Federal Fluminense University evaluated the game and offered the same opinions as the students. During game play at the science fair, it was possible to observe the interest of visitors who considered the game fun.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]ff.br. ORCID
Carlos Magno Rocha Ribeiro: 0000-0003-1818-6002 Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS We thank the students, teachers, and assistant teachers of the college for using the described game in their classes and in the science fair. We also thank FAPERJ for financial support.
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REFERENCES
(1) Thompson, Lord Kelvin, W. Baltmore Lectures on Molecular Dynamics and the Wave Theory of Light; C. J. Clay and Sons, Cambridge University Press Warehouse: London, 1904. (2) Gerlach, H. Handedness and Chirality. MATCH 2009, 61, 5−10. (3) Leffingwell, J. C. Chirality & Bioactivity I.: Pharmacology. Leffingwell Reports 2003, 3 (1), 1−27. (4) Wallentin, C.-J.; Orentas, E.; Warnmark, K.; Wendt, O. F. Chirality, a Never-Ending Source of Confusion. Z. Kristallogr. 2009, 224, 607−608. (5) McMurry, J. E. Organic Chemistry, 9th ed.; Cengage Learning: New York, 2016. (6) Wagner, A. J.; Miller, S. M.; Nguyen, S.; Lee, G. Y.; Rychnovsky, S. D.; Link, R. D. Undergraduate Laboratory Experiment To Determine Absolute Configuration Using Thin-Layer Chromatography. J. Chem. Educ. 2014, 91 (5), 716−721. (7) Huheey, J. E. A Novel Method for Assigning R, S Labels to Enantiomers. J. Chem. Educ. 1986, 63 (7), 598. (8) Brewster, J. H. Stereochemistry and the Origins of Life. J. Chem. Educ. 1986, 63 (8), 667. (9) Gawley, R. E. Chirality made simple: A 1- and 2-Dimensional Introduction to Stereochemistry. J. Chem. Educ. 2005, 82 (7), 1009. (10) Popova, M.; Bretz, S. L.; Hartley, C. S. Visualizing Molecular Chirality in the Organic Chemistry Laboratory Using Cholesteric Liquid Crystals. J. Chem. Educ. 2016, 93 (6), 1096−1099. (11) Kramer, W. H.; Griesbeck, A. G. The Same and Not the Same: Chirality, Topicity and Memory of Chirality. J. Chem. Educ. 2008, 85 (5), 701. (12) Wintner, C. E. Two-Dimensional Chirality in Three-Dimensional Chemistry. J. Chem. Educ. 1983, 60 (7), 550.
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SUMMARY The 3D Memory Game could help teachers meet the pedagogic goals for students of recognizing whether an object or organic compound is chiral or achiral on the basis of the perception of spatial overlap between an object and its mirror image, considering reflection and symmetry and asymmetry concepts. C
DOI: 10.1021/acs.jchemed.7b00219 J. Chem. Educ. XXXX, XXX, XXX−XXX
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(13) Scalfani, V. F.; Vaid, T. P. 3D Printed Molecules and Extended Solid Models for Teaching Symmetry and Points Groups. J. Chem. Educ. 2014, 91 (8), 1174−1180. (14) Harle, M.; Towns, M. A Review of Spatial Ability Literature, Its Connection to Chemistry, and Implications for Instruction. J. Chem. Educ. 2011, 88 (3), 351−360. (15) Antunes, M.; Pacheco, M. A. R.; Giovanela, M. Design and Implementation of Educational Game for Teaching Chemistry in Higher Education. J. Chem. Educ. 2012, 89 (4), 517−521. (16) Kordaki, M. A Constructivist, Modeling Methodology for the Design of Educational Card Games. ProcediaSoc. Behav. Sci. 2015, 191, 26−30. (17) Prensky, M. Digital Game−Based Learning, 2nd ed.; Paragon House: St. Paul, MN, 2007. (18) Soares, M. H. F. Jogos e Atividades Lúdicas para o Ensino de ́ Quimica, 1st ed.; Kelps: Goiânia, 2013. (19) Sjöström, J.; Talanquer, V. Humanizing Chemistry Education: From Simple Contextualization to Multifaceted Problematization. J. Chem. Educ. 2014, 91 (8), 1125−1131. (20) Wikipedia entry for Concentration (game). https://en.wikipedia. org/wiki/Concentration_(game) (accessed June 2017). (21) Wilhelm, J. H. Playing with Organic Reactions Mechanisms − ReMeM:BER, an Educational Memory Game. World J. Chem. Educ. 2016, 4 (5), 114−116.
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DOI: 10.1021/acs.jchemed.7b00219 J. Chem. Educ. XXXX, XXX, XXX−XXX
