Article

Cite This: J. Chem. Educ. 2018, 95, 791−803 pubs.acs.org/jchemeduc

MOL: Developing a European-Style Board Game To Teach Organic

Chemistry
Eduardo Triboni* and Gabrielle 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
See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.

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
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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

■ INTRODUCTION
Organic chemistry courses usually constitute at least one of the
encouraging the students not only to listen but to talk, write,
and therefore reflect on the content, active learning methods
central disciplines of a vast and diverse set of undergraduate foster a cooperative cycle of questioning and clarification that
programs ranging from hard science careers (e.g., chemistry and intensifies the appropriation of knowledge.3,4
biology) to health sciences (e.g., medicine and pharmacy) Games provide an interesting approach to active learning, as
across fields like engineering. In spite of the huge differences they merge the building of knowledge with playful activities
among the aforementioned areas, the high failure rates are intensified by cheerful competition. Therefore, it is not
surprisingly homogeneous. Clearly, the complex concepts and surprising to find a vast literature on the use of games as
large amount of material covered in a typical undergraduate learning tools, in particular in the field of chemistry.5 The
organic chemistry course play a prominent role. Obviously, this success of this strategy is readily confirmed by the increasing
cannot be altered without seriously affecting the quality of the number of games that have been effectively used to teach
course. However, another common trait, the form of chemical kinetics,6−8 functional groups,9,10 general chemis-
exposition, which mostly relies on the standard lecture-based
try,11,12 organic chemistry,10,13,14 the periodic table,15 physical
approach, provides an interesting alternative to address this
problem.1,2 chemistry,16 synthetic strategy,9,14 and so on. In general, these
Active learning has recently been considered as a promising games involve minimal adaptations of traditional or mass-
strategy to increase the learning outcomes of classes, in market games.
particular in the context of organic chemistry.2 By active
learning methods we mean any instructional method that Received: June 22, 2017
actively engages the students in their learning process as Revised: February 26, 2018
opposed to the passiveness of listening to a lecture. Thus, by Published: April 5, 2018
© 2018 American Chemical Society and
Division of Chemical Education, Inc. 791 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

The present paper concerns the development and application First, we briefly consider the games that fall into the general
of a European-style board game17 in both third- and fourth- knowledge category. They are usually characterized by
semester undergraduate organic chemistry courses taught at question-and-answer or matching mechanics, so that they are
Escola de Engenharia de Lorena for chemical engineering easily adapted to different subject matters. Chemistry Taboo is a
majors. European-style board games (Eurogames) are a rendition of the guessing game Taboo developed by Capps.19
common, though still imprecise, class of tabletop games that Milton Bradley’s board game Concentration was also adapted by
emphasize strategy over luck and conflict. They usually involve Nowosielski.20
a series of simple and innovative game mechanics that together Multiple games have been developed to teach concepts
allow depth of play, requiring players to think, plan, and often related to the periodic table. In Cheminoes,21 Moreno et al.
shift tactics throughout the game. These characteristics provide adapted traditional Dominoes to teach the relationship between
an interesting framework to create a meaningful relation valence and atomic number for the first 36 elements in the
between theme and game elements, so that the game can be ́
periodic table. ChemMend,22 by Marti-Centelles et al., is a card
effectively used as a tool to promote higher-order thinking game based on the popular UNO to promote the identification
skills. Moreover, they lack player elimination, making them of period and group for each element. Kavak designed
ideal for classroom implementations. MOL (Mastering the ChemPoker, a modification of the standard 52-card poker
Organic chemistry Lab) emulates the environment of an deck based on periodic trends such as group and period of the
organic chemistry laboratory by presenting players with the periodic table.23 Elemental Periodica and Groupica are two
common choices and problems a chemist usually faces in order games developed by Bayir.24 The former is a Bingo game in
to efficiently synthesize organic compounds. Thus, it integrates which two or more players have to identify elements in the s, p,
in an innovative way several fundamental areas involved in and d blocks of the periodic table from their atomic numbers
organic chemistry, some of which have already been addressed and common properties related to daily life or technology. The
by different didactic games. latter is a set collection card game in which one to eight players
The core concepts addressed by MOL are the physical- have to collect five cards describing distinct properties of one of
chemical parameters that influence the outcome of a chemical the groups from the periodic table. Elements is a card matching
reaction, such as mass balance, probabilistic factors (effective game developed by Alexander et al.25 in which two to four
and noneffective collisions), pH, and temperature. Besides the players have to match cards with the names of elements to
mechanics derived from a microscopic description, MOL cards with their symbols. Franco-Mariscal et al.26 developed
encompasses several distinct macroscopic factors related to Families of Chemical Elements, a card game adapted from a
the management and daily routine of a chemistry laboratory, crossover of Gin Rummy and Go Fish, in which three to five
ranging from the choice and improvement of experimental players have to recognize the names, symbols, and family or
apparatuses to the struggle for financial support. It also involves group structures of all elements in the periodic table. It is worth
negative aspects such as equipment malfunction and sabotage. noting that Franco-Mariscal et al.15 implemented a complete
These concepts are approached through three possible teaching unit addressing the periodic table based on the use of
reactions involving a single common compound: triacylglycerol. educational games such as Families of Chemical Elements and
Acidic esterification/hydrolysis, transesterification, and alkaline several tasks involving play (TIPs) with promising results.
hydrolysis of triacylglycerol are examples of nucleophilic Orbital Battleship is a rendition of the classical guessing game
substitutions in acyl compounds with different reaction Battleship by Kurushkin and Mikhaylenko,27 in which two
conditions. players have to guess the opponent’s element by “shooting”
Finally, as a fun and engaging game, MOL can be effectively electrons to reveal the electronic structure.
used inside and outside the classroom to implicitly present and Several games fall into the broad category of nomenclature,
contextualize the concepts outlined above in a stress-free and chemical formulas, and equation writing. In Acid−Base Poker,
interactive environment. Zhang28 adapted a standard 52-card deck for playing Texas

■ EDUCATIONAL GAMES IN THE TEACHING OF

CHEMISTRY
Hold’em Poker to teach the concepts of acids and bases to first-
year undergraduate chemistry students. The suits represent
weak/strong acids/bases, and the cards depict molecules and
In the last few decades, educational games have been ions that are ordered according to their strengths as acids or
successfully employed as instructional devices to complement bases. Compoundica, another game by Bayir,24 modifies Ludo to
the usual teaching techniques by many chemistry instructors. reinforce the formation of ionic and covalent compounds and
These games can be categorized either by the subject matter the inert behavior of noble gases. Enthalpy Costs is an ingenious
they address5 (general knowledge (GK), elements and atomic card game developed by Bell et al.29 to review Lewis structure
structure (EAS), nomenclature, formulas, and equation writing and concepts related to bond breaking/formation and enthalpy.
(NFEW), chemical reactions (CR), or organic chemistry In this game, two to four players have to use cards depicting
(OC)) or by the platform of presentation (board games, card elements to form or modify the Lewis structures of molecules,
games, dice games, electronic games, or puzzle games). In order scoring proportionally to the enthalpies of bonds created or
to justify our choices of game design, it is fundamental to destroyed. Antunes et al.16 designed a question-and-answer
understand the current panorama of tabletop (board, card, and board game to review contents related to molecular geometry,
dice) games used in the teaching of chemistry. Therefore, in the polarity, and intermolecular forces. ChemOkey is a modification
following we provide an update to the list originally compiled of Rummikub proposed by Kavak30 to improve the learning of
by Russell.5 However, we restrict our attention to non- the names and symbols of common ions and ionic compounds
commercial tabletop games. Moreover, we focus on competitive and reinforce the electroneutrality principle. Kavak and
games, which according to Salen and Zimmerman18 constitute Yamak31 also proposed a guessing board game, Picture Chem,
“systems in which players engage in artificial conflict, defined by in which two players have to correctly identify laboratory
rules, that result in a quantifiable outcome.” equipment from clues given by the opponent. In Chemical Alias,
792 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

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

Game Topic Players Type Based on Learning
Chemical Alias32 NFEW 4+ Board Alias Drill
Chemical Jeopardy40 GK 2 Board Jeopardy Memorization
Chemistry Taboo19 GK 2−8 Board Taboo Memorization
ChemMend22 EAS 2−10 Card UNO Memorization
ChemOkey30 NFEW 4 Board Rummikub Drill
Concentration20 GK 4−5 Board Concentration Memorization
Where’s Ester?38 OC 2 Card Guess Who? Memorization
Which Pathway Am I?39 OC 2 Card Guess Who? Memorization

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

Game Topic Players Type Based on Learning
Acid−Base Poker28 NFEW 4−6 Card Poker Memorization
Chemantics41 NFEW 2+ Card Rummy Drill
Chemical Bingo42 NFEW 2+ Board Bingo Memorization
Chemical Elements Bingo43 EAS 2+ Board Bingo Memorization
Cheminoes21 EAS 2−6 Board Domino Memorization
CHeMoVer12 NFEW 2−4 Board Sorry, Parcheesi Drill
ChemPoker23 EAS 2−6 Card Poker Memorization
Coin Game Based on the Hexoses44 OC 2 Coin Ping Chiu Wang Yuan Memorization
Elemental Periodica24 EAS 2+ Board Bingo Memorization
Families of Chemical Elements26 EAS 3−5 Card Rummy, Go Fish Memorization
Go Chemistry33 NFEW 4−6 Card Go Fish Drill
Groupica24 EAS 4 Board Ludo Drill
Old Prof Card11 EAS 3−9 Card Old Maid, Go Fish Memorization
Orbital Battleship27 EAS 2 Board Battleship Drill
Organic Functional Group Playing Card Deck10 OC varies Card Go Fish, Old Maid, Rummy, Poker Memorization
Retrosynthetic Rummy14 OC 4 Card Rummy Drill
Synthetic Dominos9 OC 2−5 Card Domino Drill

Kurushkin and Mikhaylenko32 adapted the board game Alias to CHEMCompete is an original sequence formation card game
review the chemical nomenclature of acids, bases, oxides, and designed by Gogal et al.35 to teach substitution and elimination
salts. Go Fish was also adapted in Go Chemistry by Morris33 in reactions of alkyl halides. Another matching card game,
order to help students identify an element or ion from its ChemKarta, was developed by Knudtson36 to help students in
chemical symbol and to review concepts related to ionic and identifying organic functional groups in different molecules.
covalent compounds. Welsh10 also proposed an adaptation of the standard 52-card
A few games have been designed to promote learning and deck to help students recognize the names and structures of
understanding of chemical kinetics. Depletion is a clever original functional groups by playing traditional card games such as Go
board game developed by Olbris and Herzfeld6 to teach the Fish, Old Maid, Rummy, and Poker. Organic Mastery is a
concept of activation energy and the roles of temperature and question-and-answer board game proposed by Mosher et al.37
catalysts according to Eyring’s transition theory. In this to review several topics of organic chemistry. A Contract
simulative game, two to three players have to buy reactants Rummy adaptation, Retrosynthetic Rummy, was proposed by
and guide them through chemical reactions, choosing whether
Carney14 to help students practice synthetic reasoning. Synthesis
or not to accelerate the reaction by purchasing additional heat
and Synthetic Dominos were designed by Farmer and Schuman9
or catalysts. Interestingly, Depletion uses some game mechanics
to review functional groups and practice solving organic
that slightly resemble the ones commonly associated with
synthesis problems. While the latter is based on traditional
Eurogames to promote strategic play. However, the game
becomes increasingly static toward the end, and the winner is Dominoes, the former is actually a simple solitaire puzzle that
clearly identified much before the game actually ends. Also does not satisfy our working definition of a competitive game.
worthy of note is Equilibrium Principles by Edmonson and The board game Guess Who? was adapted by Angelin and
Lewis.7 Although it is a playful activity similar to the TIPs Ramström38 in Where’s Ester? and by Ooi and Sanger39 in
introduced by Franco-Mariscal 15 instead of an actual Which Pathway Am I? In the former, the goal is to learn the
competitive game, it concretely illustrates that chemical trivial names of organic compounds, whereas in the latter, the
equilibria can be simulated by the roll of dice. goal is to help students in identifying biochemical pathways.
Particularly important for our purposes are the games Even though it does not cover all of the competitive tabletop
developed for teaching organic chemistry. As we describe in the games used in the teaching of chemistry, the list obtained by
following, they address various topics ranging from nomencla- complementing Russell’s original work with our more recent
ture to synthetic reasoning. Aiming to help students learn the survey provides important insights into the development and
isomerism of monosaccharides, Costa34 adapted a standard 52- use of educational chemistry games. In order to better
card deck to play the matching card game Carbohydeck. understand the process of game design and identify how it
793 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

Table 3. Chemistry Educational Games Involving Simple Game Mechanics

Game Topic Players Type Core Mechanic Learning
A Game for Review45 GK 2 Party Submitting Memorization
Carbohydeck34 OC 2+ Card Arranging Drill
Chemical Dice42 NFEW 2+ Dice Arranging Drill
ChemKarta36 OC 4−8 Board Arranging Drill
Chemsyn-Chemical Card 146 OC 2+ Card Arranging Drill
Compoundica24 NFEW 2−8 Card Arranging Memorization
Elements25 EAS 2−4 Card Arranging Memorization
Learning Organic by Playing Cards13 OC 2−6 Card Arranging Memorization
Molecular Geometry16 NFEW 4 Board Submitting Memorization
Organic Mastery37 OC 3−6 Board Submitting Memorization
Organocards-Chemical Card 247 OC 2+ Card Arranging Drill
Organocards-Chemical Card 347 OC 2+ Card Arranging Drill
Picture Chem31 NFEW 2 Board Arranging Memorization
The Game of the Names48 OC 2 Party Submitting Memorization

can be more effectively used to improve the learning outcome, games that involve either complex game mechanics or the
we propose the following classification: interplay of several simple game mechanics. Most Eurogames
C.1 Modifications of commercial games should be classified in C.4. Finally, category C.5 (see Table 5)
C.2 Modifications of traditional games collects playful activities that fall short of Salen and Zimmer-
C.3 Games involving simple game mechanics man’s definition of games,18 lying somewhere between play and
C.4 Games involving complex game mechanics game scenarios. These so-called TIPs, as introduced by Franco-
C.5 Tasks involving play (TIPs) Mariscal et al.,15 “can include some sort of artistic or
technological creativity by the student and offer them a more
While the first two categories (see Tables 1 and 2) are self- active role.”
evident, the remaining three deserve some clarification. In C.3
Our classification yields interesting conclusions. First, almost
(see Table 3), we collect games in which the gameplay revolves
all of the games considered fall into categories C.1, C.2, and
around only one simple core game mechanic such as arranging
C.3, whereas only three games could be classified into C.4.
or submitting. For a thorough discussion regarding the different
Noting also that the majority of commercial or traditional
types of mechanics usually employed in board games, we refer
games used as templates for educational chemistry games are
the reader to Järvinen.49 According to Järvinen,49 the arranging
deeply based on the two game mechanics that define C.3,
game mechanic consists of “arranging the order, assembly, or
arranging and submitting, we can infer the following principle
location of game elements, typically components, into sets”.
guiding the usual process of game design. Game rules should be
Thus, games that primarily involve matching cards (e.g., Old
as simple and familiar as possible so that students do not have
Maid, UNO), forming sequences of cards (e.g., Rummy), or
to focus on learning how to play the game but can instead
collecting sets of cards (e.g., Rummy, Go Fish) fall into this
concentrate on improving or testing their knowledge of the
category. On the other hand, Järvinen defines submitting as
subject matter. Familiar game rules also decrease the lecture
“submitting information (in a format specified in the rules) for
time that has to be allocated to explaining the game, thus
evaluation by the game system or other players”.49 Hence,
leaving more time to actually perform the activity.
games involving answering questions or guessing keywords,
This guideline has a profound impact on the learning
such Alias, Guess Who?, and Taboo are common examples of
outcome, as it dictates the relationship between the theme
this game mechanic. Category C.4 (see Table 4) comprises
(subject matter) and the game system, also known as
thematization. There are basically two opposite approaches to
Table 4. Chemistry Educational Games Involving Complex thematization:49 (i) an existing game system is adapted to a
Game Mechanics
theme or (ii) a theme is turned into a game system. In the first
Game Topic Players Type Learning case, the theme is commonly used only to disguise familiar
CHEMCompete35 OC 2−10 Card Drill game systems, and as a consequence, it is not properly
Depletion6 CR 2−3 Board Higher-order integrated into the core dynamics of the game. This usually
Enthalpy Costs29 NFEW 2−4 Card Drill 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

Table 5. Tasks Involving Play

Game Topic Players Type Learning

Calendar Game15 EAS 2 Daily life context Higher-order
Conductors and Insulators15 EAS 2 Practical work Drill
Equilibrium Principles7 CR 2 Dice Drill
Identif ication of the Chemical Elements in Pictures15 EAS 1 Drawings Drill
Model of the Telluric Screw15 EAS 1 Model Higher-order
PT Murals15 EAS 3−5 Mural Higher-order

794 DOI: 10.1021/acs.jchemed.7b00408

J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

distinct thematized categories.49 This is exactly the case for to the emergence of complex game systems, allowing a deep
many games in categories C.1, C.2, and C.3. The ultimate and engaging play experience.17 This depth of play can then be
consequence of weak thematization in the context of used to promote a cycle of experiential learning or praxis.51
educational games is that game elements act exclusively as Usually in game design, applying a theme to the mechanics
motivation to fulfill learning activities such as memorization and and goals of a game often helps players to readily understand
drills. and assimilate the rules of the game, as they imbue a sense of
On the other hand, the second approach to thematization meaning and purpose to the actions taken in game.17 In the
can more naturally lead to a meaningful relation between theme context of didactic games, the inversion of this perspective, i.e.,
and game elements, known as strong thematization. According using the rule set as a system in which the theme is framed,
to Järvinen,49 strong thematization necessarily requires a stimulates the engagement of the player with the subject matter
complex information structure. From the pedagogical point of being taught.50 In particular, in order to win the game, the
view, it is exactly this complex information structure within the player has to understand the rules and goals, and therefore, they
game system that allows the learning of higher-order thinking unintentionally learn the subject.
skills. However, in terms of game design, implementing such a Similarly to the majority of Eurogames,17 we have chosen to
complex information structure is a subtle task because it use choosing as the primary mechanic in MOL. According to
involves careful manipulation of other game elements such as Järvinen,49 choosing is defined as a game mechanic through
components and rules. All of the games listed in category C.4 which “the player is presented with making a choice between a
achieve this to some extent. Finally, since the TIPs from number of options”. Its main implementation is given by the
category C.5 are considerably less constrained by a formal game choice of which card among a hand of three each player has to
system, they trivially evade many of the difficulties commonly play during a single turn. Depending on the card played, a
associated with implementing a complex information structure. different game submechanic is triggered. For example, reactant

■ GAME DESIGN
In this section, we discuss how the game elements in MOL
cards involve the submechanic of allocating resources, while
modulator cards involve the submechanic of upgrading/down-
grading. These submechanics reflect the usual options a chemist
were chosen to avoid the usual and ineffective carrot and stick has to fine-tune his experiment. Therefore, by forcing the player
approach to educational game design. Charsky uses this term to to make decisions similar to the ones a chemist faces in the
describe the minimal role game elements usually play in laboratory, MOL emulates the dynamical environment of a
didactic games.50 Namely, they are mostly used as a motivation chemistry laboratory in a compelling and engaging way.
to fulfill learning activities, according to the underlying principle During experiment phase, randomness is included through
that entertainment follows from the completion of such two mechanisms: first by the drawing of a random card from the
activities. Clearly, Charsky’s statement accurately describes draw deck and second through the roll of dice to determine
the scenario outlined in the previous section. In particular, by whether an effective collision happened. Similar to many
simply disguising drills, practice activities, and quizzes as games, Eurogames, MOL randomizes the resources available to each
only the learning of lower-order thinking skills and player at the beginning of each turn, before the player chooses
memorization are fostered. Hence, the typical educational which action to take. Thus, the players can use this information
game fails to teach gamers how to apply their knowledge in a to plan their strategies accordingly. This emphasizes the
critical and flexible way. The learning of such higher-order mechanic of choosing and gives players a sense of control
thinking skills usually requires a cycle of action and reflection, over their progression. Moreover, this kind of random factor,
which can be attained only if the game design naturally when carefully balanced, only serves to add more variability and
promotes a reflective practice during gameplay.51 depth to the decision-making process, as the overall effect of
Charsky50 and Ruggiero and Watson51 identify how several randomness can in principle be mitigated through skillful
game characteristics can be used to naturally promote learning play.17 On the other hand, the roll of dice at the end of a
during gameplay. The difficulty lies in merging game and player’s turn stems from the simulative approach to chemical
pedagogical elements while keeping the fun and learning in reactions through random collisions, which has already been
perfect balance.50 In other words, it ultimately reduces to the effectively used in the gamelike activity Equilibrium Principles.7
problem of achieving strong thematization without over- Thus, the outcome of an individual collision cannot be
whelming the players with game information. Building upon predicted but can only be influenced with external factors
these ideas, the question was how to create a game whose such as the modulator cards. This type of approach to random
theme emerged from the interweaving of different mechanics elements in games is reminiscent of Anglo-American games
and goals, emulating the dynamical environment of an organic such as war games or role-playing games, where emphasis is
chemistry laboratory. More importantly, the game needed to be placed on combat resolution.
fun and engaging, so that players would either want to keep Finally, one key issue to have in mind when designing a
playing it or replay it several times. By doing so and game, be it a hobby or a serious game, is maintaining player
consequently improving their gaming abilities, they would involvement throughout the game. In order to keep players
seamlessly learn the desired subject matter. interested during downtime, MOL employs a mechanism
One of the distinctive characteristics of the so-called through which players can interact with each other via action
European approach to game design is the focus on the weaving cards and surprise cards. The former makes it possible for the
of different types of mechanics to enhance playability and player during his or her turn to interact with players in
player involvement.17 By a game mechanic, we mean a downtime, usually in a destructive manner, while the latter
functional game feature through which a player can interact allows players in downtime either to evade some hindering
with either the game system or other players to influence the effects of action cards or to force any player to roll the dice
game state.17,49 Even though these mechanics are individually again, possibly taking a worse result. Moreover, in games in
simple, a carefully chosen interplay of such mechanics can lead which the endgame goal is to be the first to accumulate a given
795 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

game element (i.e., a race-type goal), there is another possible containing all of the boards shuffled together (the laboratory
difficulty in keeping players engaged: it is often the case that the deck). Then this phase proceeds in turns, with players
eventual winner is easily identifiable long before the end of the simultaneously perform one single action chosen from the
game. To combat this, several action cards, such as broken f ilter, following options:
broken centrif uge, catastrophic experiment, espionage, and • Play a single board corresponding either to the reaction
sabotage, have been introduced in MOL to help players in or extraction of his/her main product face up
the losing positions hinder the leaders, thereby maintaining the • Play a single board corresponding either to the reaction
tension.

■
or extraction of his/her main product face down
PLAYING MOL • Reveal a single face-down board by turning it face up
• Do nothing
MOL is a competitive board game in which two to six players
assume the role of chemists in charge of an organic chemistry After performing their actions, the players pass one board to
laboratory striving to find more efficient synthetic strategies. the player on their right. Finally, all players with fewer than two
The ruleset and card and board templates are provided in the boards in their hands draw one board form the laboratory deck,
Supporting Information. The boards and cards can be printed if possible. This phase ends when a player first displays the
with a color printer on heavy cardstock, cut out, and then reaction board and extraction board corresponding to his or her
laminated to increase their durability. Players will also need main product face up.
game tokens and two 10-faced dice. Both can be purchased Synthesis and Extraction Phase
inexpensively online or at local gaming stores. Alternatively, in After the laboratories are assembled, starting with the winner of
the absence of game tokens, corn or beans can be used instead. the Laboratory Assembly phase, the players take turns to
Also, there are many online or mobile applications (dice perform their reactions and extract their main products. A
rollers) that can be used to roll virtual dice. The overall cost of typical turn consists of the following steps in order:
a game set was around $20. In the remainder of this section, we
simply provide an overview of the rules and explain the 1. Draw a card
gameplay. For detailed information, we refer the reader to the 2. Play a card
ruleset and the gameplay examples provided in the Supporting 3. Perform extraction
Information. 4. Roll the dice
The object (or winning condition) of the game is to be the The cards (Figure 3) represent some of the usual choices
first player to extract a previously determined molar quantity of available to a chemist, such as buying reactants (Figure 3a),
a given main product. This quantity varies from 9 to 27 mol raising/lowering the pH or temperature (Figure 3b), and
and should be chosen according to the time available to play improving laboratory equipment (Figure 3c), along with cards
the game. Each main product is represented by a main product that allow them to mess up other laboratories (Figure 3d). By
card (Figure 1) depicting one of the following triacylglycerol- 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
Figure 1. Main Product Cards in MOL. 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
derived compounds: biodiesel, fatty acid, and fatty acid salt
chemical equation. If the result is greater than the current
(soap). During setup, all of the main product cards (two of each
conversion rate, either nothing happens or, in the case of a
main product) are shuffled together in a small deck from which
reversible reaction, such as fatty acid production, the main
each player draws one card. The subsequent gameplay is
product is converted back into the reactants, also according to
divided into two distinct phases: Laboratory Assembly and
the chemical equation. The current conversion rate represents
Synthesis and Extraction, which we clarify in the next sections.
the probability that an effective collision will take place. Since it
Laboratory Assembly Phase can be altered by modulator cards (Figure 3b), it is obtained by
Assembling the laboratory consists of laying down in front of adding to the initial conversion rate 5% for each modulator card
each player two distinct boards (Figure 2). A reaction board that favors the reaction and subtracting 5% for each modulator
(Figure 2a) represents the chemical reaction leading to one of card that hinders the reaction.
the main products. Besides the corresponding chemical Game tokens representing products are collected at the top
equation, it also displays the effect of variations of pH and of the extraction board and are ready to be extracted. The
temperature on the conversion rate. An extraction board (Figure extraction process is triggered when the player, during step 3 of
2b) represents two possible extraction processes for one of the his or her turn, chooses to move any quantity of game tokens
main products. Players initially draw two boards from a deck representing products to the first box of one of his or her
796 DOI: 10.1021/acs.jchemed.7b00408
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Journal of Chemical Education Article

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
Figure 3. Cards in MOL. scoring process. Finally, the operating submechanic consists of
rolling the dice to determine whether effective collisions took
place and products were synthesized.

■ EVALUATION
Purpose
This study aimed at exploring student’s perceptions of the use
of MOL as an educational tool regarding (i) player engage-
ment, (ii) fun, (iii) learning of higher-order thinking skills in
the context of organic chemistry, and (iv) fostering a cycle of
Figure 4. 2d10 dice rolled as a d100 die. The result of this roll is 23. experiential learning, which would enable us to indirectly assess
the possible effectiveness of our approach to game design based
extraction columns. In the following turns, again during step 3 on European games. Moreover, since MOL integrates in a
of the turn, the player moves the game tokens on the extraction single game several fundamental concepts involved in a typical
columns to the next box until they reach the Extracted main organic chemistry course, it was important to identify which of
product box at the bottom of the extraction board. Game tokens these could benefit the most from a classroom implementation
collected in the Extracted main product box represent extracted so that instructors can incorporate MOL as an activity
products and thus the player’s current score. according to their needs. Finally, we wanted to estimate the
Figure 5 shows the relations among all of the game target audience of our game.
mechanics and their influence on other game elements such
as interface and goals during the Synthesis and Extraction phase. Implementation
Choosing is the primary mechanic and consists of the player’s We implemented the Portuguese version of MOL as a
decision on which card to play during a single turn. It triggers classroom activity in the Organic Chemistry I and Organic
two submechanics: allocating and upgrading/downgrading. The Chemistry II classes for chemical engineering majors at Escola
allocating submechanic is involved when a player adds reactants de Engenharia de LorenaUniversidade de São Paulo (EEL/
797 DOI: 10.1021/acs.jchemed.7b00408
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Journal of Chemical Education Article

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 (%) Ages
12th grade 12th grade chemistry 1/2016 26 65 35 17.0 ± 0.7
OC I (16) Organic Chemistry I 1/2016 31 58 42 19.7 ± 1.0
OC I (17) Organic Chemistry I 1/2017 28 68 32 20.1 ± 1.7
OC II Organic Chemistry II 2/2016 18 56 44 20.1 ± 0.8

USP) and in a chemistry class of the Brazilian equivalent of activity, while the game worked as a review session in the latter.
12th grade (or senior year) of North American high school at Regardless of the audience, the in-class activity was the same.
Colégio Técnico de Lorena (COTEL). The original Portuguese After an initial introduction, taking around 25 min and
version of MOL, depicted in Figure 6, was called LEB, an consisting of a brief explanation of the gameplay, students
acronym for Laboratório de Ensino Básico, which roughly were asked to form groups of three to five people and play
translates to “Basic Teaching Laboratory”. MOL. Given the constrained amount of lecture time (2 h), we
The intervention occurred in the beginning of the respective set the winning condition to be the extraction of 9 mol, so a
courses for samples OC I (17) and OC II and midway through typical game took about 50 min. Finally, the students were
the semester for samples 12th grade and OC I (16). Thus, in the asked to complete a short questionnaire evaluating their gaming
former case the concepts were first introduced during the game and learning experiences.
798 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

Participants insight regarding the effectiveness of MOL in promoting a cycle

In this section we characterize the four samples of students of praxis. In addition to this survey, an instructor’s observation
employed in this study: students enrolled in a 12th grade diary was used to register how each session progressed and
chemistry class during the first semester of 2016, students reflections on the learning processes that took place.
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
■ RESULTS AND DISCUSSION
According to the observation diaries, in all of the classroom
semester of 2016. Table 6 indicates the numbers of participants, implementations student’s expectations were clearly and evenly
percentages of males and females, and ages in the four samples. polarized before starting to play. One group anticipated a
All of the students were assumed to have some previous basic difficult and complex game in which a heavy focus on learning
knowledge of general chemistry regarding stoichiometry, mass elements would severely compromise the fun and therefore
balance, limiting reactant, reaction conditions, and reaction lead to a boring and hollow experience. This should not come
yield, since these subject matters are covered in typical high as a surprise, given the hindsight provided by their gaming
school chemistry courses before the 12th grade. Moreover, background and the usual approach to pedagogical games. On
before being able to enroll in any organic chemistry course, the other hand, there are always open-minded students who
chemical engineering majors at EEL/USP have to succeed at were genuinely looking forward to playing MOL. Despite this
two general chemistry courses,52 in which such concepts are clear initial division, once the actual game test started, the
addressed in more detail and new concepts regarding the classroom mood drastically changed from apathy to excitement.
kinetic and thermodynamic aspects of chemical reactions are The students seemed to be evidently engaged and actually
introduced. Finally, students attending Organic Chemistry II striving to win the game. They were extremely competitive.
have passed Organic Chemistry I,53 in which the basic Several manifestations corroborating these observations were
mechanisms of organic reactions are covered. left as answers to question Q.8. For example, one student
It was also important for our purposes to understand the wrote, “Before playing, I expected an extremely boring game.
gaming habits of the participating students. Table 7 shows the My expectations were greatly surpassed because besides being
educational, the game was superf un.” Another student wrote, “It
Table 7. Gaming Habits of the Students Involved in This exceeded my expectations. I have never had more fun playing
Survey other educational games.” Also, many students left statements
such as “The game was engaging and dynamic.”
Sample Students That Play Tabletop Games (%)
Further evidence supporting the claim that the overall
12th grade 57.7 gaming and learning experience was a great success is provided
OC I (16) 64.5 by the answers to question Q.3. According to Table 8, in all of
OC I (17) 77.8 the samples the majority of students attested that playing MOL
OC II 88.9 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
percentages of students who claimed to play tabletop games on
importantly, no student agreed with the statement that playing
a regular basis. However, they mostly played traditional games
MOL neither was fun nor stimulated the learning of chemistry.
(e.g., chess, checkers, truco) or mass-market games (e.g.,
In the 12th grade sample, only one student chose the None of
Monopoly, Risk, The Game of Life, UNO), with a few notable
the above option, claiming that MOL only clarified organic
exceptions who claimed to play trading card games (e.g., Magic:
reactions that he had previously learned. As for the two
The Gathering, Yu-Gi-Yo) and tabletop role-playing games (e.g.,
students in the OC I (16) sample who chose the None of the
Dungeons & Dragons, GURPS). More importantly for our study,
above option, they claimed that playing MOL was only fun.
only one student among the 103 participating in the tests
Moreover, from the fact that at least 75% of the participants
claimed to play European-style board games such as The Settlers
would actually like to buy MOL, we can infer that MOL is a
of Catan. Thus, our sample consisted mostly of casual gamers, as
sufficiently engaging game that players want to either keep
opposed to what are usually called hardcore or hobby gamers,
playing or replay it several times. Some students even claimed
who were unbiased toward European games.
that “MOL is one of the best games I have ever played.”
Finally, it is worth noting that at both EEL/USP and COTEL
Regarding the pedagogical relevance of MOL, the answers to
there is a habit of testing and implementing new pedagogical
question Q.1 clearly indicate that it can be effectively used as a
tools, so the students were somewhat used to this kind of
teaching tool from high school to higher education, depending
experience and the use of games in the classroom.
only on the instructor’s approach to the subject matter. The
Instrument majority of students from all samples not only could relate the
The student’s perceptions regarding the use of MOL as a concepts addressed by the game to the concepts studied during
pedagogical tool were investigated with the use of a very simple their regular courses but also agreed that MOL was able to
questionnaire (see Figure 7). It consisted of three parts. The present them in a clear and concise way, thereby clarifying such
first part, consisting of age, sex, and question Q.1, was used to concepts. Moreover, the open-ended question Q.7 allowed us
characterize our samples. The second part, questions Q.2 to to identify which of the chemical concepts could benefit the
Q.6, was in the form of a poll and assessed the overall gaming most from a classroom implementation of MOL. Table 9 shows
experience by asking participants to choose the statement that that MOL can be particularly useful in reviewing general
best described their opinion. Finally, the third part, comprising concepts regarding organic reactions from high school to
open-ended questions Q.7 and Q.8, was designed to determine introductory courses on organic chemistry. However, more
which chemical concepts the students found to be clarified by advanced students, such as the ones in Organic Chemistry II,
playing MOL. Moreover, it allowed us to gain further unbiased did not consider MOL relevant in this topic, probably because
799 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
Journal of Chemical Education Article

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 Although it is a complex game, according to question Q.5
concepts. On the other hand, the impact of MOL on the students did not consider it be confusing or hard to play. More
understanding of how certain conditions can influence the importantly, they agreed that MOL clearly emulates the
reaction rate increases as we apply it to more advanced dynamics of an organic chemistry laboratory. Furthermore,
audiences. This can be further clarified by comparing the majority of students enrolled in Organic Chemistry I who
statements from students in the 12th grade sample (e.g., “By claimed to have never been in an organic chemistry laboratory
playing MOL, I understood that there are some conditions that indicated that MOL had helped them to visualize how an
favor the products of a chemical reaction and others that organic chemistry laboratory routine is. According to some
don’t”) with statements from participants in the OC II sample students, “The game is very good! I learned about chemical
(e.g., “MOL clarified in a very dynamic and interactive way how reactions. Also, as I relaxed I could imagine myself working in a
certain conditions such as pH and temperature influence the lab.”
reaction rate.”). Thus, even though MOL can be used to Student’s perceptions regarding their performance in the
elucidate some concepts related to chemical kinetics to high game can be used to validate the conclusion that MOL is not
school students, only undergraduate students seem to properly too complicated to be used as a pedagogical activity. According
benefit from this feature. This behavior is manifested more to question Q.4, only two students in one sample (OC I (17))
evidently when we consider the more abstract concept of claimed that their performance was bad because the game was
activation energy. In this case, only students in Organic too complex. It is worth noting that most students that chose
Chemistry II noted a partial effectiveness of MOL in illustrating the None of the above option were complaining about bad luck
this notion and its relation to probability. According to the or extremely competitive opponents. Thus, given the gaming
students in the OC II sample, “MOL was useful in clarifying background of our test group, we can conclude that MOL is
many concepts, specially the relation between activation energy still a simple and accessible game that can be learned in a short
and the probability of an effective collision” and “MOL helped amount of time. In addition, question Q.4 reveals that to some
me to understand the influence of reaction conditions on the extent MOL implements a cycle of experiential learning, since
activation energy better.” Finally, student’s perceptions some students stated that their performance improved as they
concerning the learning of extraction methods were surprisingly understood which parameters affected their chemical reactions
homogeneous and an indicative that MOL slightly helps in this and how they could interfere. Even though not that many
subject matter. students chose option (b), this conclusion is supported by the
800 DOI: 10.1021/acs.jchemed.7b00408
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Table 8. Students Responses to the Multiple-Choice Part of the Questionnaire

12th grade OC I (16) OC I (17) OC II
Question/Answer (%) (%) (%) (%)
Q.2 What was the relevance of playing MOL?
(a) MOL clarified concepts that I had already learned 96 87.1 89.3 94.4
(b) I learned new concepts by playing MOL 4 6.5 10.7 0
(c) MOL didn’t teach or clarify any concept 0 6.5 0 5,6
(d) None of the above 0 0 0 0
Q.3 How was the gaming experience?
(a) I have just played MOL like any other ordinary game without learning anything 3.8 16.1 3.6 5.6
(b) I didn’t like playing MOL and it didn’t stimulate the learning of organic chemistry 0 0 0 0
(c) I enjoyed playing MOL and it stimulated the learning of organic chemistry 92.4 74.2 96.4 94.4
(d) None of the above 3.8 9.7 0 0
Q.4 How was your performance in the game?
(a) Good 65.4 71 46.4 66.7
(b) It improved as I learned more about organic chemical reactions during the game 23.1 19.4 35.7 11.1
(c) Bad, because the game is too complicated 0 0 7.1 0
(d) None of the above 11.5 9.7 10.8 22.3
Q.5 What do you think about the game dynamics?
(a) MOL clearly emulates the environment of an organic chemistry laboratory 88.5 77.4 75 94.4
(b) I have never been in an organic chemistry laboratory, but because of MOL I can imagine what 3.8 16.1 21.4 5.6
it is like
(c) The game dynamics is confusing, because I have never been in an organic chemistry 7.7 3.2 3.6 0
laboratory
(d) The game dynamics is extremely confusing 0 3.2 0 0
Q.6 If MOL were commercially available, would you buy it?
Yes 76.9 100 78.6 88.9
No 23.1 0 21.4 11.1

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 88.5 11.5 90.3 9.7 71.4 28.6 33.3 66.7
Influence of pH and temperature on the reaction rate 30.8 69.2 58.1 41.9 50 50 72.2 27.8
Activation energy 0 100 0 100 0 100 38.9 61.1
General knowledge of extraction processes 30.8 69.2 38.7 61.3 35.7 64.3 33.3 66.7

observation diary and students’ responses to question Q.8: “So,

if I raise your pH, your reaction rate will decrease” and “My
■ CONCLUSION
The results from the classroom implementations described in
performance has greatly improved by understanding the logic this study allow us to draw several conclusions regarding
behind chemical reactions through the rules of play.” students’ perceptions of the use of MOL as a pedagogical
Finally, analyzing all the responses to questions Q.7 and Q.8, activity:
we can infer that MOL has great potential to effectively • MOL is a fun and engaging game that students want to
promote the learning of higher-order thinking skills in the play several times.
context of undergraduate organic chemistry courses. This • MOL can be used to review and clarify general concepts
conjecture is supported by several comments, such as “MOL related to organic reactions involving acyl compounds
can be used as an effective learning tool, because it addresses (acidic esterification/hydrolysis, transesterification, and
many interrelated concepts regarding chemical reactions in a alkaline hydrolysis) from high school to introductory
strategic and dynamic way”, “MOL fostered the development of undergraduate courses on organic chemistry.
• MOL can be used to illustrate the influence of physical-
logical reasoning in the context of organic synthesis”, and
chemical parameters on the reaction rate and the relation
“MOL motivated me to question how different factors
between reaction conditions and reaction mechanisms
influence the reaction rate and its relation to probability”, left involving acyl compounds (acidic esterification/hydrol-
by students in samples OC I (16), OC I (17), and OC II. ysis, transesterification, and alkaline hydrolysis) in
Hence, by accurately emulating the dynamics of an organic undergraduate organic chemistry courses.
chemistry laboratory, undergraduate students were able to • MOL has the potential to promote higher-order thinking
understand how these concepts interrelate and interfere with skills.
each order, thus helping them to develop a sense of strategic • MOL has the potential to foster a cycle of experiential
thinking in the context of organic synthesis. learning.
801 DOI: 10.1021/acs.jchemed.7b00408
J. Chem. Educ. 2018, 95, 791−803
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■
Article

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jupiterweb/obterDisciplina?sgldis=LOQ4032, respectively (accessed
January 2018).
(53) The syllabi for Organic Chemistry I and Organic Chemistry II
can be found at https://uspdigital.usp.br/jupiterweb/
obterDisciplina?sgldis=LOQ4037 and https://uspdigital.usp.br/
jupiterweb/obterDisciplina?sgldis=LOQ4038, respectively (accessed
January 2018).

803 DOI: 10.1021/acs.jchemed.7b00408

J. Chem. Educ. 2018, 95, 791−803