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

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MOL: Developing a European-Style Board Game To Teach Organic Chemistry Eduardo Triboni* and Gabriel Weber* Escola de Engenharia de Lorena, Universidade de São Paulo, 12602-810 Lorena-SP, Brasil S Supporting Information *

ABSTRACT: Recently there has been a renewed interest in the development and use of pedagogical games, as they provide an interesting approach to the appropriation of knowledge in the context of active learning. However, most didactic games fail to completely implement a cycle of reflection and action, thereby fostering mostly lower-order thinking skills and memorization as opposed to critical thinking and problem solving skills. This limitation can be traced back to the ineffective carrot and stick approach to game design that is widely applied in the context of pedagogical games. In this article, we discuss the development of a pedagogical game in which the game elements were carefully chosen to seamlessly merge with the desired chemistry content and therefore create an engaging and fun learning experience. In particular, in order to allow complex concepts to naturally emerge from a simple set of rules, we followed the so-called European approach to game design. The resulting game, MOL (Mastering the Organic chemistry Laboratory), was tested with 77 students of ages between 19 and 21 enrolled in organic chemistry courses for chemical engineering majors and 26 students of ages between 17 and 18 enrolled in a 12th grade chemistry class. The results of these classroom implementations indicate that MOL clarifies several key concepts regarding organic reactions, particularly kinetic and thermodynamic aspects. Furthermore, they suggest that MOL can be effectively used to demonstrate how the aforementioned concepts interrelate in a real laboratory situation, therefore stimulating a sense of critical thinking. KEYWORDS: Organic Chemistry, Humor/Puzzles/Games, Second-Year Undergraduate, High School/Introductory Chemistry, Kinetics, Laboratory Equipment/Apparatus, Student-Centered Learning

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INTRODUCTION Organic chemistry courses usually constitute at least one of the central disciplines of a vast and diverse set of undergraduate programs ranging from hard science careers (e.g., chemistry and biology) to health sciences (e.g., medicine and pharmacy) across fields like engineering. In spite of the huge differences among the aforementioned areas, the high failure rates are surprisingly homogeneous. Clearly, the complex concepts and large amount of material covered in a typical undergraduate organic chemistry course play a prominent role. Obviously, this cannot be altered without seriously affecting the quality of the course. However, another common trait, the form of exposition, which mostly relies on the standard lecture-based approach, provides an interesting alternative to address this problem.1,2 Active learning has recently been considered as a promising strategy to increase the learning outcomes of classes, in particular in the context of organic chemistry.2 By active learning methods we mean any instructional method that actively engages the students in their learning process as opposed to the passiveness of listening to a lecture. Thus, by © XXXX American Chemical Society and Division of Chemical Education, Inc.

encouraging the students not only to listen but to talk, write, and therefore reflect on the content, active learning methods foster a cooperative cycle of questioning and clarification that intensifies the appropriation of knowledge.3,4 Games provide an interesting approach to active learning, as they merge the building of knowledge with playful activities intensified by cheerful competition. Therefore, it is not surprising to find a vast literature on the use of games as learning tools, in particular in the field of chemistry.5 The success of this strategy is readily confirmed by the increasing number of games that have been effectively used to teach chemical kinetics,6−8 functional groups,9,10 general chemistry,11,12 organic chemistry,10,13,14 the periodic table,15 physical chemistry,16 synthetic strategy,9,14 and so on. In general, these games involve minimal adaptations of traditional or massmarket games. Received: June 22, 2017 Revised: February 26, 2018

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DOI: 10.1021/acs.jchemed.7b00408 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

Article

First, we briefly consider the games that fall into the general knowledge category. They are usually characterized by question-and-answer or matching mechanics, so that they are easily adapted to different subject matters. Chemistry Taboo is a rendition of the guessing game Taboo developed by Capps.19 Milton Bradley’s board game Concentration was also adapted by Nowosielski.20 Multiple games have been developed to teach concepts related to the periodic table. In Cheminoes,21 Moreno et al. adapted traditional Dominoes to teach the relationship between valence and atomic number for the first 36 elements in the ́ periodic table. ChemMend,22 by Marti-Centelles et al., is a card game based on the popular UNO to promote the identification of period and group for each element. Kavak designed ChemPoker, a modification of the standard 52-card poker deck based on periodic trends such as group and period of the periodic table.23 Elemental Periodica and Groupica are two games developed by Bayir.24 The former is a Bingo game in which two or more players have to identify elements in the s, p, and d blocks of the periodic table from their atomic numbers and common properties related to daily life or technology. The latter is a set collection card game in which one to eight players have to collect five cards describing distinct properties of one of the groups from the periodic table. Elements is a card matching game developed by Alexander et al.25 in which two to four players have to match cards with the names of elements to cards with their symbols. Franco-Mariscal et al.26 developed Families of Chemical Elements, a card game adapted from a crossover of Gin Rummy and Go Fish, in which three to five players have to recognize the names, symbols, and family or group structures of all elements in the periodic table. It is worth noting that Franco-Mariscal et al.15 implemented a complete teaching unit addressing the periodic table based on the use of educational games such as Families of Chemical Elements and several tasks involving play (TIPs) with promising results. Orbital Battleship is a rendition of the classical guessing game Battleship by Kurushkin and Mikhaylenko,27 in which two players have to guess the opponent’s element by “shooting” electrons to reveal the electronic structure. Several games fall into the broad category of nomenclature, chemical formulas, and equation writing. In Acid−Base Poker, Zhang28 adapted a standard 52-card deck for playing Texas Hold’em Poker to teach the concepts of acids and bases to firstyear undergraduate chemistry students. The suits represent weak/strong acids/bases, and the cards depict molecules and ions that are ordered according to their strengths as acids or bases. Compoundica, another game by Bayir,24 modifies Ludo to reinforce the formation of ionic and covalent compounds and the inert behavior of noble gases. Enthalpy Costs is an ingenious card game developed by Bell et al.29 to review Lewis structure and concepts related to bond breaking/formation and enthalpy. In this game, two to four players have to use cards depicting elements to form or modify the Lewis structures of molecules, scoring proportionally to the enthalpies of bonds created or destroyed. Antunes et al.16 designed a question-and-answer board game to review contents related to molecular geometry, polarity, and intermolecular forces. ChemOkey is a modification of Rummikub proposed by Kavak30 to improve the learning of the names and symbols of common ions and ionic compounds and reinforce the electroneutrality principle. Kavak and Yamak31 also proposed a guessing board game, Picture Chem, in which two players have to correctly identify laboratory equipment from clues given by the opponent. In Chemical Alias,

The present paper concerns the development and application of a European-style board game17 in both third- and fourthsemester undergraduate organic chemistry courses taught at Escola de Engenharia de Lorena for chemical engineering majors. European-style board games (Eurogames) are a common, though still imprecise, class of tabletop games that emphasize strategy over luck and conflict. They usually involve a series of simple and innovative game mechanics that together allow depth of play, requiring players to think, plan, and often shift tactics throughout the game. These characteristics provide an interesting framework to create a meaningful relation between theme and game elements, so that the game can be effectively used as a tool to promote higher-order thinking skills. Moreover, they lack player elimination, making them ideal for classroom implementations. MOL (Mastering the Organic chemistry Lab) emulates the environment of an organic chemistry laboratory by presenting players with the common choices and problems a chemist usually faces in order to efficiently synthesize organic compounds. Thus, it integrates in an innovative way several fundamental areas involved in organic chemistry, some of which have already been addressed by different didactic games. The core concepts addressed by MOL are the physicalchemical parameters that influence the outcome of a chemical reaction, such as mass balance, probabilistic factors (effective and noneffective collisions), pH, and temperature. Besides the mechanics derived from a microscopic description, MOL encompasses several distinct macroscopic factors related to the management and daily routine of a chemistry laboratory, ranging from the choice and improvement of experimental apparatuses to the struggle for financial support. It also involves negative aspects such as equipment malfunction and sabotage. These concepts are approached through three possible reactions involving a single common compound: triacylglycerol. Acidic esterification/hydrolysis, transesterification, and alkaline hydrolysis of triacylglycerol are examples of nucleophilic substitutions in acyl compounds with different reaction conditions. Finally, as a fun and engaging game, MOL can be effectively used inside and outside the classroom to implicitly present and contextualize the concepts outlined above in a stress-free and interactive environment.

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EDUCATIONAL GAMES IN THE TEACHING OF CHEMISTRY In the last few decades, educational games have been successfully employed as instructional devices to complement the usual teaching techniques by many chemistry instructors. These games can be categorized either by the subject matter they address5 (general knowledge (GK), elements and atomic structure (EAS), nomenclature, formulas, and equation writing (NFEW), chemical reactions (CR), or organic chemistry (OC)) or by the platform of presentation (board games, card games, dice games, electronic games, or puzzle games). In order to justify our choices of game design, it is fundamental to understand the current panorama of tabletop (board, card, and dice) games used in the teaching of chemistry. Therefore, in the following we provide an update to the list originally compiled by Russell.5 However, we restrict our attention to noncommercial tabletop games. Moreover, we focus on competitive games, which according to Salen and Zimmerman18 constitute “systems in which players engage in artificial conflict, defined by rules, that result in a quantifiable outcome.” B



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Table 1. Chemistry Educational Games Based on Modifications of Commercial Games Game

Topic

Players

Type

Based on

Learning

Chemical Alias32 Chemical Jeopardy40 Chemistry Taboo19 ChemMend22 ChemOkey30 Concentration20 Where’s Ester?38 Which Pathway Am I?39

NFEW GK GK EAS NFEW GK OC OC

4+ 2 2−8 2−10 4 4−5 2 2

Board Board Board Card Board Board Card Card

Alias Jeopardy Taboo UNO Rummikub Concentration Guess Who? Guess Who?

Drill Memorization Memorization Memorization Drill Memorization Memorization Memorization

Table 2. Chemistry Educational Games Based on Modifications of Traditional Games Game

Topic

Players

Type

Based on

Learning

Acid−Base Poker28 Chemantics41 Chemical Bingo42 Chemical Elements Bingo43 Cheminoes21 CHeMoVer12 ChemPoker23 Coin Game Based on the Hexoses44 Elemental Periodica24 Families of Chemical Elements26 Go Chemistry33 Groupica24 Old Prof Card11 Orbital Battleship27 Organic Functional Group Playing Card Deck10 Retrosynthetic Rummy14 Synthetic Dominos9

NFEW NFEW NFEW EAS EAS NFEW EAS OC EAS EAS NFEW EAS EAS EAS OC OC OC

4−6 2+ 2+ 2+ 2−6 2−4 2−6 2 2+ 3−5 4−6 4 3−9 2 varies 4 2−5

Card Card Board Board Board Board Card Coin Board Card Card Board Card Board Card Card Card

Poker Rummy Bingo Bingo Domino Sorry, Parcheesi Poker Ping Chiu Wang Yuan Bingo Rummy, Go Fish Go Fish Ludo Old Maid, Go Fish Battleship Go Fish, Old Maid, Rummy, Poker Rummy Domino

Memorization Drill Memorization Memorization Memorization Drill Memorization Memorization Memorization Memorization Drill Drill Memorization Drill Memorization Drill Drill

Kurushkin and Mikhaylenko32 adapted the board game Alias to review the chemical nomenclature of acids, bases, oxides, and salts. Go Fish was also adapted in Go Chemistry by Morris33 in order to help students identify an element or ion from its chemical symbol and to review concepts related to ionic and covalent compounds. A few games have been designed to promote learning and understanding of chemical kinetics. Depletion is a clever original board game developed by Olbris and Herzfeld6 to teach the concept of activation energy and the roles of temperature and catalysts according to Eyring’s transition theory. In this simulative game, two to three players have to buy reactants and guide them through chemical reactions, choosing whether or not to accelerate the reaction by purchasing additional heat or catalysts. Interestingly, Depletion uses some game mechanics that slightly resemble the ones commonly associated with Eurogames to promote strategic play. However, the game becomes increasingly static toward the end, and the winner is clearly identified much before the game actually ends. Also worthy of note is Equilibrium Principles by Edmonson and Lewis.7 Although it is a playful activity similar to the TIPs introduced by Franco-Mariscal 15 instead of an actual competitive game, it concretely illustrates that chemical equilibria can be simulated by the roll of dice. Particularly important for our purposes are the games developed for teaching organic chemistry. As we describe in the following, they address various topics ranging from nomenclature to synthetic reasoning. Aiming to help students learn the isomerism of monosaccharides, Costa34 adapted a standard 52card deck to play the matching card game Carbohydeck.

CHEMCompete is an original sequence formation card game designed by Gogal et al.35 to teach substitution and elimination reactions of alkyl halides. Another matching card game, ChemKarta, was developed by Knudtson36 to help students in identifying organic functional groups in different molecules. Welsh10 also proposed an adaptation of the standard 52-card deck to help students recognize the names and structures of functional groups by playing traditional card games such as Go Fish, Old Maid, Rummy, and Poker. Organic Mastery is a question-and-answer board game proposed by Mosher et al.37 to review several topics of organic chemistry. A Contract Rummy adaptation, Retrosynthetic Rummy, was proposed by Carney14 to help students practice synthetic reasoning. Synthesis and Synthetic Dominos were designed by Farmer and Schuman9 to review functional groups and practice solving organic synthesis problems. While the latter is based on traditional Dominoes, the former is actually a simple solitaire puzzle that does not satisfy our working definition of a competitive game. The board game Guess Who? was adapted by Angelin and Ramström38 in Where’s Ester? and by Ooi and Sanger39 in Which Pathway Am I? In the former, the goal is to learn the trivial names of organic compounds, whereas in the latter, the goal is to help students in identifying biochemical pathways. Even though it does not cover all of the competitive tabletop games used in the teaching of chemistry, the list obtained by complementing Russell’s original work with our more recent survey provides important insights into the development and use of educational chemistry games. In order to better understand the process of game design and identify how it C



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Table 3. Chemistry Educational Games Involving Simple Game Mechanics Game

Topic

Players

Type

Core Mechanic

Learning

A Game for Review45 Carbohydeck34 Chemical Dice42 ChemKarta36 Chemsyn-Chemical Card 146 Compoundica24 Elements25 Learning Organic by Playing Cards13 Molecular Geometry16 Organic Mastery37 Organocards-Chemical Card 247 Organocards-Chemical Card 347 Picture Chem31 The Game of the Names48

GK OC NFEW OC OC NFEW EAS OC NFEW OC OC OC NFEW OC

2 2+ 2+ 4−8 2+ 2−8 2−4 2−6 4 3−6 2+ 2+ 2 2

Party Card Dice Board Card Card Card Card Board Board Card Card Board Party

Submitting Arranging Arranging Arranging Arranging Arranging Arranging Arranging Submitting Submitting Arranging Arranging Arranging Submitting

Memorization Drill Drill Drill Drill Memorization Memorization Memorization Memorization Memorization Drill Drill Memorization Memorization

games that involve either complex game mechanics or the interplay of several simple game mechanics. Most Eurogames should be classified in C.4. Finally, category C.5 (see Table 5) collects playful activities that fall short of Salen and Zimmerman’s definition of games,18 lying somewhere between play and game scenarios. These so-called TIPs, as introduced by FrancoMariscal et al.,15 “can include some sort of artistic or technological creativity by the student and offer them a more active role.” Our classification yields interesting conclusions. First, almost all of the games considered fall into categories C.1, C.2, and C.3, whereas only three games could be classified into C.4. Noting also that the majority of commercial or traditional games used as templates for educational chemistry games are deeply based on the two game mechanics that define C.3, arranging and submitting, we can infer the following principle guiding the usual process of game design. Game rules should be as simple and familiar as possible so that students do not have to focus on learning how to play the game but can instead concentrate on improving or testing their knowledge of the subject matter. Familiar game rules also decrease the lecture time that has to be allocated to explaining the game, thus leaving more time to actually perform the activity. This guideline has a profound impact on the learning outcome, as it dictates the relationship between the theme (subject matter) and the game system, also known as thematization. There are basically two opposite approaches to thematization:49 (i) an existing game system is adapted to a theme or (ii) a theme is turned into a game system. In the first case, the theme is commonly used only to disguise familiar game systems, and as a consequence, it is not properly integrated into the core dynamics of the game. This usually leads to what is called weak thematization. A fitting example of weak thematization is given by any adaptation of the standard 52-card deck, where the numbers 1−52 are grouped into four

can be more effectively used to improve the learning outcome, we propose the following classification: C.1 Modifications of commercial games C.2 Modifications of traditional games C.3 Games involving simple game mechanics C.4 Games involving complex game mechanics C.5 Tasks involving play (TIPs) While the first two categories (see Tables 1 and 2) are selfevident, the remaining three deserve some clarification. In C.3 (see Table 3), we collect games in which the gameplay revolves around only one simple core game mechanic such as arranging or submitting. For a thorough discussion regarding the different types of mechanics usually employed in board games, we refer the reader to Järvinen.49 According to Järvinen,49 the arranging game mechanic consists of “arranging the order, assembly, or location of game elements, typically components, into sets”. Thus, games that primarily involve matching cards (e.g., Old Maid, UNO), forming sequences of cards (e.g., Rummy), or collecting sets of cards (e.g., Rummy, Go Fish) fall into this category. On the other hand, Järvinen defines submitting as “submitting information (in a format specified in the rules) for evaluation by the game system or other players”.49 Hence, games involving answering questions or guessing keywords, such Alias, Guess Who?, and Taboo are common examples of this game mechanic. Category C.4 (see Table 4) comprises Table 4. Chemistry Educational Games Involving Complex Game Mechanics Game

Topic

Players

Type

Learning

CHEMCompete35 Depletion6 Enthalpy Costs29

OC CR NFEW

2−10 2−3 2−4

Card Board Card

Drill Higher-order Drill

Table 5. Tasks Involving Play Game

Topic

Players

Type

Learning

Calendar Game15 Conductors and Insulators15 Equilibrium Principles7 Identif ication of the Chemical Elements in Pictures15 Model of the Telluric Screw15 PT Murals15

EAS EAS CR EAS EAS EAS

2 2 2 1 1 3−5

Daily life context Practical work Dice Drawings Model Mural

Higher-order Drill Drill Drill Higher-order Higher-order

D



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distinct thematized categories.49 This is exactly the case for many games in categories C.1, C.2, and C.3. The ultimate consequence of weak thematization in the context of educational games is that game elements act exclusively as motivation to fulfill learning activities such as memorization and drills. On the other hand, the second approach to thematization can more naturally lead to a meaningful relation between theme and game elements, known as strong thematization. According to Järvinen,49 strong thematization necessarily requires a complex information structure. From the pedagogical point of view, it is exactly this complex information structure within the game system that allows the learning of higher-order thinking skills. However, in terms of game design, implementing such a complex information structure is a subtle task because it involves careful manipulation of other game elements such as components and rules. All of the games listed in category C.4 achieve this to some extent. Finally, since the TIPs from category C.5 are considerably less constrained by a formal game system, they trivially evade many of the difficulties commonly associated with implementing a complex information structure.

to the emergence of complex game systems, allowing a deep and engaging play experience.17 This depth of play can then be used to promote a cycle of experiential learning or praxis.51 Usually in game design, applying a theme to the mechanics and goals of a game often helps players to readily understand and assimilate the rules of the game, as they imbue a sense of meaning and purpose to the actions taken in game.17 In the context of didactic games, the inversion of this perspective, i.e., using the rule set as a system in which the theme is framed, stimulates the engagement of the player with the subject matter being taught.50 In particular, in order to win the game, the player has to understand the rules and goals, and therefore, they unintentionally learn the subject. Similarly to the majority of Eurogames,17 we have chosen to use choosing as the primary mechanic in MOL. According to Järvinen,49 choosing is defined as a game mechanic through which “the player is presented with making a choice between a number of options”. Its main implementation is given by the choice of which card among a hand of three each player has to play during a single turn. Depending on the card played, a different game submechanic is triggered. For example, reactant cards involve the submechanic of allocating resources, while modulator cards involve the submechanic of upgrading/downgrading. These submechanics reflect the usual options a chemist has to fine-tune his experiment. Therefore, by forcing the player to make decisions similar to the ones a chemist faces in the laboratory, MOL emulates the dynamical environment of a chemistry laboratory in a compelling and engaging way. During experiment phase, randomness is included through two mechanisms: first by the drawing of a random card from the draw deck and second through the roll of dice to determine whether an effective collision happened. Similar to many Eurogames, MOL randomizes the resources available to each player at the beginning of each turn, before the player chooses which action to take. Thus, the players can use this information to plan their strategies accordingly. This emphasizes the mechanic of choosing and gives players a sense of control over their progression. Moreover, this kind of random factor, when carefully balanced, only serves to add more variability and depth to the decision-making process, as the overall effect of randomness can in principle be mitigated through skillful play.17 On the other hand, the roll of dice at the end of a player’s turn stems from the simulative approach to chemical reactions through random collisions, which has already been effectively used in the gamelike activity Equilibrium Principles.7 Thus, the outcome of an individual collision cannot be predicted but can only be influenced with external factors such as the modulator cards. This type of approach to random elements in games is reminiscent of Anglo-American games such as war games or role-playing games, where emphasis is placed on combat resolution. Finally, one key issue to have in mind when designing a game, be it a hobby or a serious game, is maintaining player involvement throughout the game. In order to keep players interested during downtime, MOL employs a mechanism through which players can interact with each other via action cards and surprise cards. The former makes it possible for the player during his or her turn to interact with players in downtime, usually in a destructive manner, while the latter allows players in downtime either to evade some hindering effects of action cards or to force any player to roll the dice again, possibly taking a worse result. Moreover, in games in which the endgame goal is to be the first to accumulate a given

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GAME DESIGN In this section, we discuss how the game elements in MOL were chosen to avoid the usual and ineffective carrot and stick approach to educational game design. Charsky uses this term to describe the minimal role game elements usually play in didactic games.50 Namely, they are mostly used as a motivation to fulfill learning activities, according to the underlying principle that entertainment follows from the completion of such activities. Clearly, Charsky’s statement accurately describes the scenario outlined in the previous section. In particular, by simply disguising drills, practice activities, and quizzes as games, only the learning of lower-order thinking skills and memorization are fostered. Hence, the typical educational game fails to teach gamers how to apply their knowledge in a critical and flexible way. The learning of such higher-order thinking skills usually requires a cycle of action and reflection, which can be attained only if the game design naturally promotes a reflective practice during gameplay.51 Charsky50 and Ruggiero and Watson51 identify how several game characteristics can be used to naturally promote learning during gameplay. The difficulty lies in merging game and pedagogical elements while keeping the fun and learning in perfect balance.50 In other words, it ultimately reduces to the problem of achieving strong thematization without overwhelming the players with game information. Building upon these ideas, the question was how to create a game whose theme emerged from the interweaving of different mechanics and goals, emulating the dynamical environment of an organic chemistry laboratory. More importantly, the game needed to be fun and engaging, so that players would either want to keep playing it or replay it several times. By doing so and consequently improving their gaming abilities, they would seamlessly learn the desired subject matter. One of the distinctive characteristics of the so-called European approach to game design is the focus on the weaving of different types of mechanics to enhance playability and player involvement.17 By a game mechanic, we mean a functional game feature through which a player can interact with either the game system or other players to influence the game state.17,49 Even though these mechanics are individually simple, a carefully chosen interplay of such mechanics can lead E



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containing all of the boards shuffled together (the laboratory deck). Then this phase proceeds in turns, with players simultaneously perform one single action chosen from the following options: • Play a single board corresponding either to the reaction or extraction of his/her main product face up • Play a single board corresponding either to the reaction or extraction of his/her main product face down • Reveal a single face-down board by turning it face up • Do nothing After performing their actions, the players pass one board to the player on their right. Finally, all players with fewer than two boards in their hands draw one board form the laboratory deck, if possible. This phase ends when a player first displays the reaction board and extraction board corresponding to his or her main product face up.

game element (i.e., a race-type goal), there is another possible difficulty in keeping players engaged: it is often the case that the eventual winner is easily identifiable long before the end of the game. To combat this, several action cards, such as broken f ilter, broken centrif uge, catastrophic experiment, espionage, and sabotage, have been introduced in MOL to help players in the losing positions hinder the leaders, thereby maintaining the tension.

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PLAYING MOL MOL is a competitive board game in which two to six players assume the role of chemists in charge of an organic chemistry laboratory striving to find more efficient synthetic strategies. The ruleset and card and board templates are provided in the Supporting Information. The boards and cards can be printed with a color printer on heavy cardstock, cut out, and then laminated to increase their durability. Players will also need game tokens and two 10-faced dice. Both can be purchased inexpensively online or at local gaming stores. Alternatively, in the absence of game tokens, corn or beans can be used instead. Also, there are many online or mobile applications (dice rollers) that can be used to roll virtual dice. The overall cost of a game set was around $20. In the remainder of this section, we simply provide an overview of the rules and explain the gameplay. For detailed information, we refer the reader to the ruleset and the gameplay examples provided in the Supporting Information. The object (or winning condition) of the game is to be the first player to extract a previously determined molar quantity of a given main product. This quantity varies from 9 to 27 mol and should be chosen according to the time available to play the game. Each main product is represented by a main product card (Figure 1) depicting one of the following triacylglycerol-

Synthesis and Extraction Phase

After the laboratories are assembled, starting with the winner of the Laboratory Assembly phase, the players take turns to perform their reactions and extract their main products. A typical turn consists of the following steps in order: 1. Draw a card 2. Play a card 3. Perform extraction 4. Roll the dice The cards (Figure 3) represent some of the usual choices available to a chemist, such as buying reactants (Figure 3a), raising/lowering the pH or temperature (Figure 3b), and improving laboratory equipment (Figure 3c), along with cards that allow them to mess up other laboratories (Figure 3d). By playing a reactant card, a player adds a certain number of game tokens, each representing 1 mol of the corresponding reactant, to the reaction board. If by the end of a turn the player has the reactants in the stoichiometric ratio, the roll of the dice will decide whether effective collisions take place and the reactants in the solution are converted to products. The two 10-faced dice (2d10) rolled together work as a single percentile die (d100 or d%), with one d10 designated as the tens digit and the other as the units digit (see Figure 4). The result of the roll, a number between 1 and 100, is then compared to the current conversation rate. If the result is less than or equal to the current conversion rate, the reaction takes place, and the player removes the mole tokens corresponding to the reactants involved in this reaction from the reaction board and adds mole tokens representing the main product formed in this reaction to the extraction board according to the chemical equation. If the result is greater than the current conversion rate, either nothing happens or, in the case of a reversible reaction, such as fatty acid production, the main product is converted back into the reactants, also according to the chemical equation. The current conversion rate represents the probability that an effective collision will take place. Since it can be altered by modulator cards (Figure 3b), it is obtained by adding to the initial conversion rate 5% for each modulator card that favors the reaction and subtracting 5% for each modulator card that hinders the reaction. Game tokens representing products are collected at the top of the extraction board and are ready to be extracted. The extraction process is triggered when the player, during step 3 of his or her turn, chooses to move any quantity of game tokens representing products to the first box of one of his or her

Figure 1. Main Product Cards in MOL.

derived compounds: biodiesel, fatty acid, and fatty acid salt (soap). During setup, all of the main product cards (two of each main product) are shuffled together in a small deck from which each player draws one card. The subsequent gameplay is divided into two distinct phases: Laboratory Assembly and Synthesis and Extraction, which we clarify in the next sections. Laboratory Assembly Phase

Assembling the laboratory consists of laying down in front of each player two distinct boards (Figure 2). A reaction board (Figure 2a) represents the chemical reaction leading to one of the main products. Besides the corresponding chemical equation, it also displays the effect of variations of pH and temperature on the conversion rate. An extraction board (Figure 2b) represents two possible extraction processes for one of the main products. Players initially draw two boards from a deck F



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Figure 2. Boards in MOL.

to the reaction board or selects an amount of product to extract. The upgrading/downgrading submechanic is responsible for allowing players to modify the reaction conditions of their reactions or those of other players. It is also involved when players improve their laboratory equipment or destroy the equipment in any opponent’s laboratory. The point-to-point movement submechanic is used to move game tokens through consecutive turns of extraction and therefore is involved in the scoring process. Finally, the operating submechanic consists of rolling the dice to determine whether effective collisions took place and products were synthesized.

Figure 3. Cards in MOL.

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EVALUATION

Purpose

This study aimed at exploring student’s perceptions of the use of MOL as an educational tool regarding (i) player engagement, (ii) fun, (iii) learning of higher-order thinking skills in the context of organic chemistry, and (iv) fostering a cycle of experiential learning, which would enable us to indirectly assess the possible effectiveness of our approach to game design based on European games. Moreover, since MOL integrates in a single game several fundamental concepts involved in a typical organic chemistry course, it was important to identify which of these could benefit the most from a classroom implementation so that instructors can incorporate MOL as an activity according to their needs. Finally, we wanted to estimate the target audience of our game.

Figure 4. 2d10 dice rolled as a d100 die. The result of this roll is 23.

extraction columns. In the following turns, again during step 3 of the turn, the player moves the game tokens on the extraction columns to the next box until they reach the Extracted main product box at the bottom of the extraction board. Game tokens collected in the Extracted main product box represent extracted products and thus the player’s current score. Figure 5 shows the relations among all of the game mechanics and their influence on other game elements such as interface and goals during the Synthesis and Extraction phase. Choosing is the primary mechanic and consists of the player’s decision on which card to play during a single turn. It triggers two submechanics: allocating and upgrading/downgrading. The allocating submechanic is involved when a player adds reactants

Implementation

We implemented the Portuguese version of MOL as a classroom activity in the Organic Chemistry I and Organic Chemistry II classes for chemical engineering majors at Escola de Engenharia de LorenaUniversidade de São Paulo (EEL/ G



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Figure 5. Interweaving of game mechanics in the Synthesis and Extraction phase. Game mechanics are displayed in green, interface elements in orange, and goals in blue.

Figure 6. Chemical engineering majors playing MOL.

Table 6. Characteristics of the Student Samples Sample

Course

Semester/Year

Participants

Males (%)

Females (%)

12th grade OC I (16) OC I (17) OC II

12th grade chemistry Organic Chemistry I Organic Chemistry I Organic Chemistry II

1/2016 1/2016 1/2017 2/2016

26 31 28 18

65 58 68 56

35 42 32 44

USP) and in a chemistry class of the Brazilian equivalent of 12th grade (or senior year) of North American high school at Colégio Técnico de Lorena (COTEL). The original Portuguese version of MOL, depicted in Figure 6, was called LEB, an acronym for Laboratório de Ensino Básico, which roughly translates to “Basic Teaching Laboratory”. The intervention occurred in the beginning of the respective courses for samples OC I (17) and OC II and midway through the semester for samples 12th grade and OC I (16). Thus, in the former case the concepts were first introduced during the game

Ages 17.0 19.7 20.1 20.1

± ± ± ±

0.7 1.0 1.7 0.8

activity, while the game worked as a review session in the latter. Regardless of the audience, the in-class activity was the same. After an initial introduction, taking around 25 min and consisting of a brief explanation of the gameplay, students were asked to form groups of three to five people and play MOL. Given the constrained amount of lecture time (2 h), we set the winning condition to be the extraction of 9 mol, so a typical game took about 50 min. Finally, the students were asked to complete a short questionnaire evaluating their gaming and learning experiences. H



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Participants

insight regarding the effectiveness of MOL in promoting a cycle of praxis. In addition to this survey, an instructor’s observation diary was used to register how each session progressed and reflections on the learning processes that took place.

In this section we characterize the four samples of students employed in this study: students enrolled in a 12th grade chemistry class during the first semester of 2016, students enrolled in the Organic Chemistry I course during the first semester of 2016 or the first semester of 2017, and students enrolled in the Organic Chemistry II course during the second semester of 2016. Table 6 indicates the numbers of participants, percentages of males and females, and ages in the four samples. All of the students were assumed to have some previous basic knowledge of general chemistry regarding stoichiometry, mass balance, limiting reactant, reaction conditions, and reaction yield, since these subject matters are covered in typical high school chemistry courses before the 12th grade. Moreover, before being able to enroll in any organic chemistry course, chemical engineering majors at EEL/USP have to succeed at two general chemistry courses,52 in which such concepts are addressed in more detail and new concepts regarding the kinetic and thermodynamic aspects of chemical reactions are introduced. Finally, students attending Organic Chemistry II have passed Organic Chemistry I,53 in which the basic mechanisms of organic reactions are covered. It was also important for our purposes to understand the gaming habits of the participating students. Table 7 shows the

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RESULTS AND DISCUSSION According to the observation diaries, in all of the classroom implementations student’s expectations were clearly and evenly polarized before starting to play. One group anticipated a difficult and complex game in which a heavy focus on learning elements would severely compromise the fun and therefore lead to a boring and hollow experience. This should not come as a surprise, given the hindsight provided by their gaming background and the usual approach to pedagogical games. On the other hand, there are always open-minded students who were genuinely looking forward to playing MOL. Despite this clear initial division, once the actual game test started, the classroom mood drastically changed from apathy to excitement. The students seemed to be evidently engaged and actually striving to win the game. They were extremely competitive. Several manifestations corroborating these observations were left as answers to question Q.8. For example, one student wrote, “Before playing, I expected an extremely boring game. My expectations were greatly surpassed because besides being educational, the game was superf un.” Another student wrote, “It exceeded my expectations. I have never had more fun playing other educational games.” Also, many students left statements such as “The game was engaging and dynamic.” Further evidence supporting the claim that the overall gaming and learning experience was a great success is provided by the answers to question Q.3. According to Table 8, in all of the samples the majority of students attested that playing MOL was fun and engaging and that by playing it they wanted to learn more about organic chemistry. Only a few students noted that they played MOL just like any ordinary game. More importantly, no student agreed with the statement that playing MOL neither was fun nor stimulated the learning of chemistry. In the 12th grade sample, only one student chose the None of the above option, claiming that MOL only clarified organic reactions that he had previously learned. As for the two students in the OC I (16) sample who chose the None of the above option, they claimed that playing MOL was only fun. Moreover, from the fact that at least 75% of the participants would actually like to buy MOL, we can infer that MOL is a sufficiently engaging game that players want to either keep playing or replay it several times. Some students even claimed that “MOL is one of the best games I have ever played.” Regarding the pedagogical relevance of MOL, the answers to question Q.1 clearly indicate that it can be effectively used as a teaching tool from high school to higher education, depending only on the instructor’s approach to the subject matter. The majority of students from all samples not only could relate the concepts addressed by the game to the concepts studied during their regular courses but also agreed that MOL was able to present them in a clear and concise way, thereby clarifying such concepts. Moreover, the open-ended question Q.7 allowed us to identify which of the chemical concepts could benefit the most from a classroom implementation of MOL. Table 9 shows that MOL can be particularly useful in reviewing general concepts regarding organic reactions from high school to introductory courses on organic chemistry. However, more advanced students, such as the ones in Organic Chemistry II, did not consider MOL relevant in this topic, probably because

Table 7. Gaming Habits of the Students Involved in This Survey Sample

Students That Play Tabletop Games (%)

12th grade OC I (16) OC I (17) OC II

57.7 64.5 77.8 88.9

percentages of students who claimed to play tabletop games on a regular basis. However, they mostly played traditional games (e.g., chess, checkers, truco) or mass-market games (e.g., Monopoly, Risk, The Game of Life, UNO), with a few notable exceptions who claimed to play trading card games (e.g., Magic: The Gathering, Yu-Gi-Yo) and tabletop role-playing games (e.g., Dungeons & Dragons, GURPS). More importantly for our study, only one student among the 103 participating in the tests claimed to play European-style board games such as The Settlers of Catan. Thus, our sample consisted mostly of casual gamers, as opposed to what are usually called hardcore or hobby gamers, who were unbiased toward European games. Finally, it is worth noting that at both EEL/USP and COTEL there is a habit of testing and implementing new pedagogical tools, so the students were somewhat used to this kind of experience and the use of games in the classroom. Instrument

The student’s perceptions regarding the use of MOL as a pedagogical tool were investigated with the use of a very simple questionnaire (see Figure 7). It consisted of three parts. The first part, consisting of age, sex, and question Q.1, was used to characterize our samples. The second part, questions Q.2 to Q.6, was in the form of a poll and assessed the overall gaming experience by asking participants to choose the statement that best described their opinion. Finally, the third part, comprising open-ended questions Q.7 and Q.8, was designed to determine which chemical concepts the students found to be clarified by playing MOL. Moreover, it allowed us to gain further unbiased I



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Figure 7. Sample questionnaire used to assess student’s perceptions regarding the use of MOL as an educational activity. It has been translated from Portuguese to English by the authors.

students at this stage have already mastered such simpler concepts. On the other hand, the impact of MOL on the understanding of how certain conditions can influence the reaction rate increases as we apply it to more advanced audiences. This can be further clarified by comparing statements from students in the 12th grade sample (e.g., “By playing MOL, I understood that there are some conditions that favor the products of a chemical reaction and others that don’t”) with statements from participants in the OC II sample (e.g., “MOL clarified in a very dynamic and interactive way how certain conditions such as pH and temperature influence the reaction rate.”). Thus, even though MOL can be used to elucidate some concepts related to chemical kinetics to high school students, only undergraduate students seem to properly benefit from this feature. This behavior is manifested more evidently when we consider the more abstract concept of activation energy. In this case, only students in Organic Chemistry II noted a partial effectiveness of MOL in illustrating this notion and its relation to probability. According to the students in the OC II sample, “MOL was useful in clarifying many concepts, specially the relation between activation energy and the probability of an effective collision” and “MOL helped me to understand the influence of reaction conditions on the activation energy better.” Finally, student’s perceptions concerning the learning of extraction methods were surprisingly homogeneous and an indicative that MOL slightly helps in this subject matter.

Although it is a complex game, according to question Q.5 students did not consider it be confusing or hard to play. More importantly, they agreed that MOL clearly emulates the dynamics of an organic chemistry laboratory. Furthermore, the majority of students enrolled in Organic Chemistry I who claimed to have never been in an organic chemistry laboratory indicated that MOL had helped them to visualize how an organic chemistry laboratory routine is. According to some students, “The game is very good! I learned about chemical reactions. Also, as I relaxed I could imagine myself working in a lab.” Student’s perceptions regarding their performance in the game can be used to validate the conclusion that MOL is not too complicated to be used as a pedagogical activity. According to question Q.4, only two students in one sample (OC I (17)) claimed that their performance was bad because the game was too complex. It is worth noting that most students that chose the None of the above option were complaining about bad luck or extremely competitive opponents. Thus, given the gaming background of our test group, we can conclude that MOL is still a simple and accessible game that can be learned in a short amount of time. In addition, question Q.4 reveals that to some extent MOL implements a cycle of experiential learning, since some students stated that their performance improved as they understood which parameters affected their chemical reactions and how they could interfere. Even though not that many students chose option (b), this conclusion is supported by the J



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Table 8. Students Responses to the Multiple-Choice Part of the Questionnaire 12th grade (%)

Question/Answer Q.2 What was the relevance of playing MOL? (a) MOL clarified concepts that I had already learned (b) I learned new concepts by playing MOL (c) MOL didn’t teach or clarify any concept (d) None of the above Q.3 How was the gaming experience? (a) I have just played MOL like any other ordinary game without learning anything (b) I didn’t like playing MOL and it didn’t stimulate the learning of organic chemistry (c) I enjoyed playing MOL and it stimulated the learning of organic chemistry (d) None of the above Q.4 How was your performance in the game? (a) Good (b) It improved as I learned more about organic chemical reactions during the game (c) Bad, because the game is too complicated (d) None of the above Q.5 What do you think about the game dynamics? (a) MOL clearly emulates the environment of an organic chemistry laboratory (b) I have never been in an organic chemistry laboratory, but because of MOL I can imagine what it is like (c) The game dynamics is confusing, because I have never been in an organic chemistry laboratory (d) The game dynamics is extremely confusing Q.6 If MOL were commercially available, would you buy it? Yes No

OC I (16) (%)

OC I (17) (%)

OC II (%)

96 4 0 0

87.1 6.5 6.5 0

89.3 10.7 0 0

94.4 0 5,6 0

3.8 0 92.4 3.8

16.1 0 74.2 9.7

3.6 0 96.4 0

5.6 0 94.4 0

65.4 23.1 0 11.5

71 19.4 0 9.7

46.4 35.7 7.1 10.8

66.7 11.1 0 22.3

88.5 3.8

77.4 16.1

75 21.4

94.4 5.6

7.7

3.2

3.6

0

0

3.2

0

0

78.6 21.4

88.9 11.1

76.9 23.1

100 0

Table 9. Chemical Concepts Clarified by MOL According to the Answers to Question “Q.7 What Have You Learned by Playing MOL?” 12th grade

OC I (16)

OC I (17)

OC II

Subject Matter

Yes (%)

No (%)

Yes (%)

No (%)

Yes (%)

No (%)

Yes (%)

No (%)

General knowledge of organic reactions Influence of pH and temperature on the reaction rate Activation energy General knowledge of extraction processes

88.5 30.8 0 30.8

11.5 69.2 100 69.2

90.3 58.1 0 38.7

9.7 41.9 100 61.3

71.4 50 0 35.7

28.6 50 100 64.3

33.3 72.2 38.9 33.3

66.7 27.8 61.1 66.7

observation diary and students’ responses to question Q.8: “So, if I raise your pH, your reaction rate will decrease” and “My performance has greatly improved by understanding the logic behind chemical reactions through the rules of play.” Finally, analyzing all the responses to questions Q.7 and Q.8, we can infer that MOL has great potential to effectively promote the learning of higher-order thinking skills in the context of undergraduate organic chemistry courses. This conjecture is supported by several comments, such as “MOL can be used as an effective learning tool, because it addresses many interrelated concepts regarding chemical reactions in a strategic and dynamic way”, “MOL fostered the development of logical reasoning in the context of organic synthesis”, and “MOL motivated me to question how different factors influence the reaction rate and its relation to probability”, left by students in samples OC I (16), OC I (17), and OC II. Hence, by accurately emulating the dynamics of an organic chemistry laboratory, undergraduate students were able to understand how these concepts interrelate and interfere with each order, thus helping them to develop a sense of strategic thinking in the context of organic synthesis.

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CONCLUSION The results from the classroom implementations described in this study allow us to draw several conclusions regarding students’ perceptions of the use of MOL as a pedagogical activity: • MOL is a fun and engaging game that students want to play several times. • MOL can be used to review and clarify general concepts related to organic reactions involving acyl compounds (acidic esterification/hydrolysis, transesterification, and alkaline hydrolysis) from high school to introductory undergraduate courses on organic chemistry. • MOL can be used to illustrate the influence of physicalchemical parameters on the reaction rate and the relation between reaction conditions and reaction mechanisms involving acyl compounds (acidic esterification/hydrolysis, transesterification, and alkaline hydrolysis) in undergraduate organic chemistry courses. • MOL has the potential to promote higher-order thinking skills. • MOL has the potential to foster a cycle of experiential learning. K



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Therefore, it constitutes an interesting tool that can be used in different contexts throughout the semester to improve the learning of organic chemistry. Either it can be implemented before addressing the topic using a more traditional approach so that the concepts are initially presented in a playful way that resembles the experimental practice, or it can be used after the traditional exposition to review and contextualize the concepts. It all depends on a particular instructor’s needs. Our findings suggest that the success of MOL lies in the interweaving of different yet simple game mechanics, which is characteristic of European-style board games, indicating the benefits of this alternative approach to educational game design that merges game and pedagogical elements to create a fun and engaging learning experience. Therefore, the development and evaluation of new European-style pedagogical board games is necessary to unveil the full potential of this approach. Finally, it is important to emphasize that the data analyzed in this study mostly rely on students’ perceptions and therefore on their particular points of view and honesty. To some extent, our findings were also supported by classroom observations logged in a diary by instructors involved in this project. However, to properly estimate the impact of MOL on the learning outcome, performance test results are needed. For these reasons, our conclusions are partial and serve as good indication of the relevance of the suggested approach to game design. Further research, including comparative performance tests to confirm and expand our conclusions, is currently being designed.

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REFERENCES

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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.7b00408.

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Article

MOL ruleset (ZIP) Templates for boards and card fronts and backs (ZIP) Gameplay examples (ZIP)

AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: [email protected]. ORCID

Eduardo Triboni: 0000-0001-6147-7847 Gabriel Weber: 0000-0001-6173-8859 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The authors thank L. Andreotti, M. Florido, A. Galembeck, C. Gazolla, A. Gunji, F. Menezes, L. Toledo, and T. Toledo for their involvement in some stages of this project. We are also extremely grateful to all of the students and to E. Pedrozo for their invaluable help with testing the game. G.W. thanks R. Bacani for useful discussions during the development of this project. Finally, we thank the reviewers for their extremely useful comments and suggestions that greatly improved the article. This work was partially supported by RUSP (Projeto 347) and São Paulo State Research Funding Agency, FAPESP ( E.R.T.: grant No 2015/06064-6). L



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