Activity pubs.acs.org/jchemeduc
Retrosynthetic Rummy: A Synthetic Organic Chemistry Card Game Jeffrey M. Carney* Department of Molecular Biology and Chemistry, Christopher Newport University, Newport News, Virginia 23606, United States S Supporting Information *
ABSTRACT: A deck of cards and a card game have been developed in an effort to make practicing organic chemistry and synthesis more fun for students. The game is played as a variation of rummy, in which players collect sets of similar cards and runs of cards in a synthetic sequence. This card game reviews knowledge of functional groups and reaction types and requires an ability to place many organic transformations in an appropriate order to synthesize target molecules. The game was used as a method to review secondyear organic reactions for third- and fourth-year students at the beginning of a course in advanced organic chemistry. Students enjoyed the game and even gathered to play it outside of class. Additionally, the deck of cards was constructed so it can function to give a variety of classic card games a chemistry theme. KEYWORDS: Second-Year Undergraduate, Upper-Division Undergraduate, Organic Chemistry, Humor/Puzzles/Games, Synthesis
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can be played using this deck; some examples include twoplayer gin rummy, go fish, and poker.
rganic synthesis is the principal application of the organic reactions covered in the second-year undergraduate organic chemistry course. Often undergraduate students find the number of functional groups and reactions overwhelming, which makes the use of those transformations in synthesis particularly difficult. One way to alleviate the pressure associated with challenging material is through the use of games.1 Educators have created a variety of chemistry card games which have been described recently in this journal.1−6 A few of these games have direct application for fundamental concepts in organic chemistry, including games that help students learn functional groups,7 stereochemistry,8 nomenclature,9 functional group interconversion,10 reactions of aliphatic compounds,11 and regiochemistry of aromatic ring reactions.12 One fundamental area for which a card game has not been reported is in multistep organic synthesis. A game that emphasizes typical organic functional groups, reagents, and transformations, then applies those in a logical synthetic sequence could alleviate anxiety and make course material more enjoyable. A deck of cards and a card game have been developed in an effort to make practicing organic chemistry and synthesis more fun. Since this game uses reactions typically covered in both semesters of the organic chemistry sequence, it is most appropriate for students who are in or beyond the second semester of organic chemistry. The game employs both forward synthetic reactions as well as simplification of target molecules through retrosynthetic analysis. The game play is based off of Contract Rummy, a classic rummy-style game in which players match sets of similar cards and collect sequences of consecutive cards.13 Retrosynthetic Rummy has been used in the classroom as a review for third- and fourth-year chemistry majors and minors enrolled in an advanced organic chemistry course focused on organic synthesis. Other classic card games © XXXX American Chemical Society and Division of Chemical Education, Inc.
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DESIGN OF THE DECK
The Suits
The playing deck for Retrosynthetic Rummy is based on the design of a standard 52-card deck, with 2 additional jokers, used for any typical card game. In place of the standard suits (spades, hearts, clubs, and diamonds), two syntheses are presented in both synthetic and retrosynthetic directions (Table 1). The Table 1. Suits for Retrosynthetic Rummy
a
The color black designates the suit as a forward synthesis and the color red designates the suit as a retrosynthesis.
synthetic direction is depicted in black, while the retrosynthetic direction is depicted in red. The end points for the suits are the starting material and the target molecule of each of the syntheses. After the starting material, the other cards in the forward syntheses alternate reagent, then reactant, making logical chemical transformations until the target molecule is
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dx.doi.org/10.1021/ed500657u | J. Chem. Educ. XXXX, XXX, XXX−XXX
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The Play
reached. In the retrosynthetic direction, the cards follow the reverse order, beginning at the target molecule and simplifying structure until the starting material is reached. The syntheses were designed around reactions typically discussed in the two semesters of second-year organic chemistry. The chosen steps are not meant to represent the most efficient process to synthesize the target molecules, but do represent a realistic way to reach them while also maintaining playability within the game.
The player to the left of the dealer plays first and may either take the card lying face up on the Waste pile or draw from the Stockroom. A player’s turn is over when a card the player no longer wants to hold is taken from the hand and discarded in the Waste pile. Play then continues clockwise around the table. Only when a player holds all aspects of that round’s contract may the player lay cards onto the table. Once a player has laid down the cards of the contract (Figure 1), any remaining cards from their hand that fit may be played onto sets or runs that have already been laid down by other players. A player cannot play cards on another player’s sets and runs until they have laid down the required contract. After a player lays down the required contract, no additional sets or runs may be played from their hand. A representative game in which three players have played the minimum contract, but a fourth player has yet to collect the necessary cards, is shown in Figure 2. Jokers are wild and can be used to complete a set or run in the event that card is missing, but they must remain part of the original set or run throughout the round. Should a card from a player’s hand fit in place of a Joker, that card can be played and the Joker may be moved to either end of that run. Once a player has laid down the contract, they may no longer draw from the Waste pile, but must begin their turn by drawing from the Stockroom. Once a player has “gone out,” by either playing or discarding the last card in their hand, all other players need to total the points on the cards remaining in their hand. The total for each round is summed, and the winner is the player with the lowest point total at the end of the game.
The Cards
Cards are 3.5 in. × 2.5 in. and can be made by the instructor or by students. The cards can be printed in color on cardstock and cut out. Instructions and materials for making the cards are provided in the Supporting Information. Each reactant card in the deck contains a structure that is further identified either by functional group (e.g., alkene, alcohol, carbonyl), as a starting material, or as the target molecule. Reagent cards are labeled by reaction classification, for example “Addition”, “SN2 Substitution”, or “Oxidation”. As in a normal deck of playing cards, each suit contains only one card of each type. Though functional groups may repeat, designations of those duplicates as “Starting Material” and “Target Molecule” prevent those cards from being playable as that functional group. Jokers have also been added to the deck to function as wild cards, increasing the chances of completing sets and runs. Rummy games use point values to calculate a score for each player at the end of the round. Since there are no numerical rankings on Retrosynthetic Rummy cards, point values have been added to keep score; reagent cards are worth 5 points, reactant cards are worth 10, starting material cards are worth 20, target molecules are worth 40, and jokers are worth 50 points.
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Requesting Cards Out of Turn
If at any time the player to move does not choose the top card on the Waste pile, the first player to ask may take that card and draw a penalty card from the Stockroom without discarding. Play continues with the player to move drawing the next card from the Stockroom. This can be done on the very first card turned face up. This rule allows for a player who is waiting for a particular card to complete their set or run to have a chance to do so rather than see the card remain unused in the Waste pile. Once a discarded card has been passed by everyone, it cannot be taken even if exposed again. A player who has laid down their contract may no longer request discarded cards. Any number of cards may be requested in a round, but a player can take a maximum of only three cards, along with the three penalty cards, per round.
GAMEPLAY
The Deal
Two decks should be used for four players. The dealer should shuffle and deal 11 cards to each player. After the deal, the discard pile (Waste) is started by taking the top card of the deck, turning it face up, and placing it next to the remainder of the deck (Stockroom).
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Object of Play
The object of the game is to get rid of all of the cards in your hand by laying down sets of three or more of a kind and/or runs of four or more cards of the same suit. In Retrosynthetic Rummy, each round requires a different “Contract” to be met before a player can lay cards from their hand onto the table (Table 2).
EVALUATION Retrosynthetic Rummy has been played in an advanced organic chemistry class of third- and fourth-year chemistry majors and minors as a means to refresh students on the functional groups, reagents, and transformations from second-year organic chemistry. With a class size of 24 students, the students worked in pairs to manage their hands, and each game comprised four pairs of students. In a smaller class, students could work independently. Introduction of the game and two rounds of play were comfortably finished in the 50 min class time. The game was very well received by students. They were excited and the element of competition further motivated student involvement. A number of students enjoyed it so much they even borrowed the decks on multiple occasions to play outside of class. The game was challenging and required a good review of some fundamental reactions. This allowed the course
Table 2. Contracts Required for Each Round of Retrosynthetic Rummy Round
Hint
Minimum Required Cards To Lay Down
1 2 3 4 5 6
6 cards (2 × 3) 7 cards (3 + 4) 8 cards (2 × 4) 9 cards (3 × 3) 10 cards (2 × 3) + 4 11 cards (2 × 4) + 3
2 sets of 3 set of 3 + run of 4 2 runs of 4 3 sets of 3 2 sets of 3 + run of 4 set of 3 + 2 runs of 4 B
dx.doi.org/10.1021/ed500657u | J. Chem. Educ. XXXX, XXX, XXX−XXX
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Figure 1. An example of a fulfilled contract that a player must have before playing cards on the table in Round 5 (2 sets of 3 and a run of 4).
comparison with the known transformations from the game. Since there are no numerical rankings on the cards, sequences of reactions required knowledge of the overall syntheses depicted on the cards, which was much less intuitive than counting in a standard deck. This challenge enhanced student cooperation. A cheat sheet displaying the full deck was handed out to aid in play, and it can be found in the Supporting Information.
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CONCLUSIONS Chemistry games provide a beneficial method to engage students in a classroom in different ways than lecturing or group work. Retrosynthetic Rummy was used to promote interaction as students refreshed material they often struggle to remember. Students responded positively and got to see another fun side of synthetic organic chemistry. The game can also be used, in addition to regular studying, as an exciting exercise in preparing for the final exam of a second-year organic chemistry course. In this setting, another possible use of the deck would be to have students race to place each the suits in the correct order as fast as they can. Because the deck of cards can function in place of a normal deck of playing cards, it can be used to give a number of classic card games a chemistry theme. Additional decks can be designed using the strategy of Retrosynthetic Rummy to incorporate different target molecules and highlight different reactions, e.g., reductions, the aldol reaction, or aromatic substitutions. This would add more
Figure 2. A representative game of Retrosynthetic Rummy in Round 2, where the minimum contract is one set of 3 and a run of 4. Cards are drawn from the Stockroom pile (face down) and discarded into the Waste (face up) in the center of the table. In this example, three players have laid the minimum contract and may play remaining cards on the sets and runs showing. The fourth player may only draw and discard until completing and laying down the contract.
to focus more intently on the application of these and new reactions in synthesis, and enabled students to identify logical bond disconnections in retrosynthetic analysis through C
dx.doi.org/10.1021/ed500657u | J. Chem. Educ. XXXX, XXX, XXX−XXX
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variety to the game and allow the course instructor to emphasize certain transformations.
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ASSOCIATED CONTENT
* Supporting Information S
A summary of game rules, pages containing the fronts and backs of cards for printing, and a cheat sheet which includes all of the cards in the deck printed in sequence. This material is available via the Internet at http://pubs.acs.org.
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AUTHOR INFORMATION
Corresponding Author
*E-mail: Jeff
[email protected]. Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS The author would like to thank Tiffany K. Baxter Carney for assistance during the design of the game, and Douglas J. Schauer and Kathryn E. Cole for their assistance in revising this manuscript.
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REFERENCES
(1) Granath, P. L.; Russell, J. V. Using Games to Teach Chemistry. 1. The Old Prof Card Game. J. Chem. Educ. 1999, 76, 485−486. (2) Sevcik, R. S.; Hicks, O.; Schultz, L. D.; Alexander, S. V. ElementsA Card Game of Chemical Names and Symbols. J. Chem. Educ. 2008, 85, 514−515. (3) Morris, T. A. Go Chemistry: A Card Game to Help Students Learn Chemical Formulas. J. Chem. Educ. 2011, 88, 1397−1399. (4) Franco-Mariscal, A. J.; Cano-Iglesias, M. J. Elemental B-O-Ne-S. J. Chem. Educ. 2011, 88, 1551−1552. (5) Kavak, N. ChemPoker. J. Chem. Educ. 2012, 89, 522−523. (6) Russell, J. V. Using Games To Teach Chemistry. J. Chem. Educ. 1999, 76, 481−484. (7) Welsh, M. J. Organic Functional Group Playing Card Deck. J. Chem. Educ. 2003, 80, 426−427. (8) Costa, M. J. Carbohydeck: A Card Game To Teach the Stereochemistry of Carbohydrates. J. Chem. Educ. 2007, 84, 977−978. (9) Angelin, M.; Ramström, O. Where’s Ester? A Game that Seeks the Structures Hiding Behind Trivial Names. J. Chem. Educ. 2010, 87, 406−407. (10) Eglinton, G.; Maxwell, J. R. ChemsynChemical Card Game 1. Educ. Chem. 1971, 8, 142−144. (11) Kristol, D.; Perlmutter, H. D. OrganocardsChemical Card Game 2. Educ. Chem. 1971, 8, 145. (12) Kristol, D.; Perlmutter, H. D. OrganocardsChemical Card Game 3. Educ. Chem. 1971, 8, 176−177. (13) Morehead, A. H., Ed.; Official Rules of Card Games, 55th ed.; The United States Playing Card Company: Cincinnati, OH, 1968.
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