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Classroom
In this section of Resonance, we invite readers to pose questions likely to be raised in a
classroom situation. We may suggest strategies for dealing with them, or invite responses,
or both. “Classroom” is equally a forum for raising broader issues and sharing personal
experiences and viewpoints on matters related to teaching and learning science.
A G Samuelson
Card Games and Chemistry Department of Inorganic and
Teaching Organometallic Reactions Through Card Games Physical Chemistry
Indian Institute of Science
Bangalore 560 012, India.
Email: ashoka@iisc.ac.in
We present a card game suitable for classroom use to pro-
vide an interactive and lively experience while studying
organometallic reactions, synthesis and catalysis. It is based
on a deck of playing cards, and we call it CARS (Catalysis
and Reaction Sequences). The object is to arrange a set of
random cards served to the player in a correct sequence. The
correct sequence is based on the sequence of steps found in
the catalytic cycle of a set of reactions. The game is similar
to the popular multiplayer card game rummy. We illustrate
the game with a set of cards based on the C–C bond forming
reactions, but it can be modified by the teacher to suit the top-
ics being taught and could even be converted to a web-based
version or a stand-alone study tool operating on a computer.
Introduction
Systematization and teaching of inorganic and organometallic
chemistry reactions are daunting tasks. Teachers and students
are bogged down by the prospect of studying literally hundreds
of ‘seemingly’ unrelated reactions. Anything that facilitates this Keywords
process and helps in visualizing relationships is welcome. If one Catalysis, organometallic
chemistry, card games, fun in
understands for example, how several organometallic reactions
chemistry.
RESONANCE | August 2018 915CLASSROOM
follow a common pattern in catalytic and stoichiometric reac-
tions, it would be a great help to the student and teacher alike. By
By writing the catalytic writing the catalytic cycles presented in organometallic chemistry
cycles presented in as a set of sequential reactions, it is possible to see that many reac-
organometallic tions indeed follow a pattern. It becomes easier for the student to
chemistry as a set of
sequential reactions, it is connect a large number of reactions and attempt the construction
possible to see that many of new catalytic cycles, given the reactants and products.
reactions indeed follow a
pattern. Games have been used effectively for enhancing student involve-
ment and making the student-teacher interaction more enjoyable
than lecture-based classes [1]. In the past, games have aided
chemical education especially in the nomenclature of compounds,
study of elements in the periodic table and reactions [2]. Some of
them are indeed card games to aid the study of nomenclature [3],
formulas [4] and even improve the understanding of stereochem-
istry [5]. Recently, there have been some excellent descriptions
of card games for teaching functional groups in organic chemistry
[6], synthetic organic chemistry [7, 8], and one to teach retrosyn-
thetic analysis [9].
We believe an extremely simple and general version of the popu-
lar card game – rummy – can be devised to learn organometallic
chemistry and catalysis. We will illustrate the idea using a set of
cards based on organometallic catalytic cycles using organic/organo-
metallic synthesis. They are only illustrative and the game is
designed in such a way that it can be used in different learn-
ing/teaching situations wherever a sequence of events is part of
the learning objective.
The deck of cards is patterned after the familiar 54 cards in com-
mon card games. The cards are divided into four groups or suits,
each one representing a catalytic cycle (as in spades, clubs or
clovers, diamonds and hearts). The name of each reaction is
printed on a color-coded card and the substrates, products and
reagents, if any, in that reaction are printed in the same color.
The transformations or steps in the reaction can also be made into
cards indicative of the reaction type such as oxidative addition,
insertion or transmetallation, reductive elimination, ligand disso-
ciation, etc. Each reaction cycle is thus mapped into a set of 12
916 RESONANCE | August 2018CLASSROOM cards. In order to increase the element of fun, one card, desig- nated as a wild or special card, is included in each suit, and this may be used to fill in any part of the sequence. Two additional cards are generic multicolored ‘wild’ cards that can be used for any reaction (across suits), reagent or sequence, making a total of 54 cards. Although the popular game of rummy is suggested, other games could be devised as well as the cards map to a regular pack of 54 cards in a deck. We will illustrate how this game can be used to teach/learn several C–C bond forming reactions where the catalytic cycles bear some resemblance. When the catalytic cycles are grouped together in this fashion, the similarities and differences are brought out, and student understanding is significantly enhanced during the play. We have chosen four named reactions: HECK, NEGISHI, SUZUKI and SONOGHASHIRA. Each of these named reactions has a well-established catalytic cycle. Apart from the fact that the common catalyst of choice is a palladium complex, three of these reactions proceed through steps that are similar in the beginning and in the end. The Heck reaction has significant differences. The game allows the students to recognize the similarities and appre- ciate the differences. If the game is played in class after these reactions are taught, or right after the lecture in a tutorial class, it is easy for students to recollect these steps. It also allows the student to construct new cycles for reactions they encounter in the literature with ease. Figure 1 shows the catalytic cycle for the Heck reaction and Fig- ure 2 shows the representative cards one can generate from this cycle. A similar exercise with the other three reactions would yield the requisite number of cards. A complete set of 54 cards is given in the supplementary section for the four reactions men- tioned above. These card sets are only illustrative. Any four reac- tions could be substituted for these C–C bond-forming reactions. One only needs to simplify the steps so that the reaction is com- pletely represented by 12 to 13 cards. In order to play the game with two to four people, one pack of cards is thoroughly shuffled to generate a random set and each RESONANCE | August 2018 917
CLASSROOM
player is dealt a set of 10 cards. The remaining cards are kept
aside face down as the stockpile. Each player tries to arrange the
ten cards (s)he has according to a reaction sequence. The object
of the game is to be the first one to arrange all the cards in valid
sequences. Valid sequences could be formed as a sequence of 10
cards from one complete catalytic cycle (same color cards). Wild
or special cards are permitted. If they are two different sequences
they could be from two different catalytic cycles of say, a set of
7 in one cycle and a set of 3 from another, or even three different
sequences of 3, 3 and 4. Players get to draw from the stockpile
and discard unwanted cards until they can form sequences. In our
experience, sequences are generated by at least one player within
15–20 minutes. After the winner is confirmed, every player shows
their sequences to other players and then a lively discussion fol-
lows. In one group, the students helped one another form all four
sequences further reinforcing the learning experience.
Although we emphasize the similarity with numbered cards, a
caveat must be added. Sequences in CARS could have some dif-
ferences from the classic card sequences. For example, in a reac-
tion of A + B transformed by a substitution reaction ‘R’ to give
C + D; the sequence could be cards corresponding to ‘A, B, R’ or
‘B, A, R’ or ‘R, C, D’ or ‘R, D, C’. All of them are chemically
meaningful. However, the sequence ‘B, R, and C’ is not consid-
ered a valid ‘reaction sequence’ although based on numbers it is
a valid sequence. Rules regarding this must be announced before
starting the game.
A player can choose to A player can choose to put down a run or sequence of three (min-
put down a run or imum), four or seven cards in the centre of the playing area. This
sequence of three might allow another player to continue the catalytic sequence by
(minimum), four or
seven cards in the centre adding a set. The object of the game is to help the students build
of the playing area. This the catalytic cycle or parts of it using the cards. So putting down
might allow another the sequences as and when they form could help them recognize
player to continue the the catalytic cycles, the reactions and the substrates. This may
catalytic sequence by
adding a set. increase the educational value. When played in this fashion, the
person who puts down all the cards first wins. However, as a
matter of strategy, many players choose not to put it down!
918 RESONANCE | August 2018CLASSROOM
Figure 1. The catalytic
cycle of the Heck reaction:
(LD = ligand dissociation;
OA = oxidative addition; LS
= ligand substituttion; MI =
migratory insertion; HE = β-
hydride elimination; RE =
reductive elimination.
The student learns different aspects of a catalytic cycle such as the
requirement for a vacant site, a suitable oxidation state, matching
substrates and catalysts in a lively environment. In the first few
rounds of the game, students may be permitted to use their class
notes or even have access to complete catalytic cycles. If needed,
an easier card set could be printed with suitable hints on the cards
suggesting what reactions are possible for the substrate or what
substrates are suitable for the reaction. In an electronic version of
the game, this could be made easier through the use of help files
or simpler card sets.
In order to play this game to aid self-study, one can play the equiv-
alent of a ‘Single Suit Spider’. Multiple copies, usually eight, of
the same (reaction) colored cards are needed to play this game.
Both Rummy and Spider are readily played with these cards, and
hence the games should be transferable to soft versions. Simi-
larly, with some modifications, a board game like ‘Snakes and
Ladders’ could be constructed using the sequence. Board games
RESONANCE | August 2018 919CLASSROOM
Figure 2. Representa-
tive cards generated from
the Heck reaction cycle pre-
sented in Figure 1.
have the advantage that they could even be elaborated into social
games such as ‘Farmville’. The framework described here is also
suitable for further elaboration by increasing the difficulty level,
and adding gaming elements so that a full-fledged gaming expe-
rience can be incorporated in the future. Converting the game
into an app suitable for the mobile, or a web-based program in-
dependent of device architecture should also help more students
to participate. If a gaming environment is provided, additional
motivational aspects can set in, such as the desire to role play,
gaining social recognition, a sense of accomplishment, handling
challenges, mystery and fun that can lead to interactive and en-
joyable learning. An excellent opportunity for ‘gamification’ of
920 RESONANCE | August 2018CLASSROOM
Figure 3. Set of 54
cards suitable for printing
on a plastic sheet. To
download a set of print-
able cards please visit:
https://is.gd/ZwUdVh
learning exists [10]. We believe the incorporation of such games
either through physical cards/boards or even through computer
games or apps will improve the motivation and engagement of
students.
Conclusions
Teaching organometallic reaction mechanisms and catalytic cy-
cles using card games, in a fun-filled interactive setting is more
effective than a slide presentation or even a chalk and board lec-
ture. Since the game is tunable, it is likely to be of great value
in teaching other topics where sequences are involved: such as in
total synthesis. We have described here a general framework for
converting any complex reaction with multiple steps into a card
game very similar to rummy, the popular game of cards. Many
opportunities open up once the teacher converts the learning ob-
jective into a game [11].
Supporting Information
This section illustrates the set of 54 cards (Figure 3) suitable for
printing on a plastic sheet. The sequence number is printed below
the cards for the teacher’s reference. Detailed instructions for
playing the game is as follows.
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Instructions for Playing the Card Game – CARS
In order to play the game with four people, the cards are thor-
oughly shuffled to generate a random set and each player is dealt
a set of 10 cards. The remaining cards are kept aside face down
as the stockpile. The first player, takes a card from the stock and
attempts to improve on the number of sequences (s)he has in hand
(10 cards), and then discards any unwanted card with its face up.
The next player in a similar fashion can take one card (DRAW)
from the top of the stock or the card that was discarded by the pre-
vious player. However, each player must put back (DISCARD)
the most unwanted card from her/his cards, or the card that was
taken from the stock. So, at any stage of the game except during
the player’s turn, one has only 10 cards on hand. When one player
finally forms three sequences, (s)he is declared the winner. If the
stock is exhausted, the set of open cards are shuffled and replaced
face down to form a fresh stock to continue the game.
Acknowledgments
The author thanks the students of the organometallic course who
have participated in the game and several faculty members of IITs
who have given valuable feedback.
Suggested Reading
[1] M J Samide, A M Wilson, Games, Games, Games; Playing to Engage with
Chemistry Concepts, Chem. Educ., Vol.19, pp.167–170, 2014.
[2] J V Russell, Using Games to Teach Chemistry: An Annotated Bibliography. J.
Chem. Educ., Vol.76, pp.481–484, 1999.
[3] R S Sevcik, L D Schultz, S V Alexander, Elements – A Card Game of Chemical
Names and Symbols, J. Chem. Educ., Vol.85, pp.514–515, 2008.
[4] T A Morris, Go Chemistry: A Card Game to Help Students to Learn Chemical
Formulas, J. Chem. Educ., Vol.88, pp.1397–99, 2011.
[5] M J Costa, Carbohydeck: A Card Game To Teach the Stereochemistry of Car-
bohydrates, J. Chem. Educ., Vol.84, pp.977–978, 2007.
[6] M J Welsh, Organic functional Group Playing Card Deck, J. Chem. Educ.,
Vol.80, pp.426–427, 2003.
922 RESONANCE | August 2018CLASSROOM
[7] C A Knudtson, ChemKarta: A Card Game for Teaching Functional Groups
in Undergraduate Organic Chemistry, J. Chem. Educ., Vol.92, pp.1514–1517,
2015.
[8] S C Farmer, M K Schuman, A Simple Card Game to Teach Synthesis in Or-
ganic Chemistry Courses, J. Chem. Educ., Vol.93, pp.695–698, 2016.
[9] J M Carney, Retrosynthetic Rummy: A Synthetic Organic Chemistry Card
Game, J. Chem. Educ., Vol.92, pp.328–331, 2015.
[10] Y-k Chou, Actionable Gamification: Beyond Points Badges and Leaderboards,
Octalysis Media, Freemont, 2014.
[11] M Antunes, M A R Pacheco, M Giovanela, Design and Implementation of
an Educational Game for Teaching Chemistry in Higher Education, J. Chem.
Educ., Vol.89, pp.517–521, 2012.
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