Activity pubs.acs.org/jchemeduc
ChemKarta: A Card Game for Teaching Functional Groups in Undergraduate Organic Chemistry Christopher A. Knudtson*,† Department of Chemistry, Midland University, Fremont, Nebraska 68025, United States S Supporting Information *
ABSTRACT: Students in undergraduate organic chemistry courses are frequently overwhelmed by the volume and complexity of information they are expected to learn. To aid in students’ learning of organic functional groups, a novel card game “ChemKarta” is reported that can serve as a useful alternative to flashcards. This pedagogy is a simple matching game, in which students identify functional groups on molecules. ChemKarta has a large card set to immerse students in course material and to allow teachers to mine the game for class and exam questions. It is easily customized by the addition or removal of cards to adjust content to fit an individual course. Students found the game easy to learn and responded favorably to its use as an educational tool. KEYWORDS: Second-year Undergraduate, Organic Chemistry, Humor/Puzzles/Games, Nomenclature/Units/Symbols, Student-Centered Learning
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The ChemKarta set presented here addresses the subject of functional groups. This subject is ubiquitous in organic courses and is often studied with flashcards. While flashcards emphasize memorization of functional groups, ChemKarta asks students to identify functional groups within an organic molecule. Memorization of all cards in the set is difficult, emphasizing problem-solving as a method for identification. Questions asking students to think beyond simple functional group recognition are also present, such as categorizing an amine as 1°, 2°, or 3°. As a result, ChemKarta provides a more layered approach to learning than traditional functional group flashcards. Overall, the present ChemKarta set addresses 22 functional groups in the context of 100 organic molecules (for simplicity, the guanidine group is treated as an imine and two amines). Eight heterocyclic structures are also included. The card set can be adjusted by adding or removing molecules to customize content. Instructors are encouraged to modify the game to incorporate examples from their own course content, research, or personal interests.
ndergraduate students frequently struggle with successful completion of introductory organic chemistry. This course is infamous for high failure rates of 40−60%.1−3 Students often find the breadth and complexity of information in an organic course daunting. Learning is made even more difficult by a negative perception of chemistry courses3−5 and underdeveloped study skills.6 A need exists for the development of novel and approachable teaching strategies to address these issues. To this end, a card game “ChemKarta” has been developed. The use of games in teaching chemistry is an established method of education.7 Educational games serve as learning activities outside of traditional lectures, homework, and exams. Educators have utilized games as interesting and enjoyable methods to promote knowledge and present material.8,9 Examples of chemistry subjects addressed through games include chemical formulas, nomenclature, the periodic table, molecular structures, and functional groups.10−15 While successful, previous pedagogical games usually adapt existing properties such as Go Fish, Taboo, and Scrabble to chemistry concepts.12−14 Building on Gredler’s principles for game creation,16 an original card game called “ChemKarta” was developed. ChemKarta is a straightforward matching game where players pair questions with the appropriate answers. Each card contains answers grouped around a theme, enabling a single card to answer multiple questions. The theme of each card also provides context to the information present. ChemKarta can be easily modified by adding or removing cards to customize the card set. The game’s fundamental design was kept simple, with the intent that it could be applied to more than one subject by changing the questions and answers on the cards. © XXXX American Chemical Society and Division of Chemical Education, Inc.
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DESIGN AND SETUP ChemKarta uses three card decks of Solution, Problem, and Bonus cards. Solution cards make up a player’s hand, and all players draw from a common Solution deck. A separate Problem deck contains questions for players to answer. Finally, a Bonus deck of eight cards addresses supplemental material (i.e., heterocyclic structures such as pyridine, furan, and indole rings). Cards may be drawn on blank notecards or printed out
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DOI: 10.1021/ed500729v J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Activity
Figure 1. Game setup: Solution cards in blue, Problem cards in red, Bonus cards in orange.
on cardstock. The cards in each deck are provided in the Supporting Information. ChemKarta is designed to work outside of class in short, informal sessions of 4−8 players, with a teacher acting as a moderator or referee. Groups of greater than eight students are assigned to teams to play. Sessions should last 30 min regardless of the number of games completed; beginning students often struggle to complete a single game, while more experienced students may complete multiple games in a single sitting. Students are allowed and encouraged to take notes during sessions, but outside references are discouraged.
Box 1. A Simple Turn It is Ella’s turn and her Problem card asks for the identification of an alcohol. She chooses a Solution card Cyanoketone and identifies the alcohol. The Honors question asks if the alcohol is 1°, 2°, 3°, or aryl. She chooses 2°, which is incorrect. She scores the normal 5 points, not 10 points. If a player is unable to solve a Problem card or answers incorrectly, he or she cannot attempt another answer and must discard their Solution card. Now, others in the group may attempt to answer the Problem card, effectively “stealing” the player’s turn. The original player chooses who may answer first if multiple players wish to make an attempt. If others are incorrect in their answers, they must discard their Solution card and cannot attempt another answer this turn. Attempts to solve the Problem card may continue until it is solved or no one can answer, at which point the card is discarded and the turn ends. At the end of the turn, the player may discard any number of cards and draw back up to six Solution cards. Players may only refill their hands at the end of their turn. Answering multiple Problem cards during others’ turns will reduce a player’s hand, so fewer Solution cards are available on that player’s turn. Additionally, eight Bonus cards are available in the middle of the table. If at any time a player answers with a Solution card that corresponds to an appropriate Bonus card, he or she may collect that card and add the points to that player’s score (Box 2 and Figure 2). Bonus cards are not refilled during the game. Play continues until a player reaches 100 points, at which point a player is declared the winner.
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RULES AND GAMEPLAY At the beginning of the game, the eight Bonus cards are laid out in the middle of the playing table face-up. The Solution and Problem decks are shuffled and each player is dealt six Solution cards face-up. The Solution and Problem decks are then placed face-down within reach of all players (the decks may be split to accomplish this) as shown in Figure 1. Players then have the opportunity to discard and replace any cards they do not like. The game proceeds in a turn-wise fashion beginning with the player on the moderator’s left. On a player’s turn, he or she turns over the top card of the Problem deck. The Problem card asks that player to identify a functional group. To answer a Problem card, a player must say the name of the Solution card and indicate the location of the functional group on the molecule. If the player solves the Problem card correctly, that player removes the Solution card from his or her hand, pairs the Solution card with the Problem card, and scores the number of points printed on the Problem card. Some cards have “Honors” questions that can be answered for additional points. If a player can answer the Honors question in addition to the initial question, that player scores the higher point value. However, if the player incorrectly answers the Honors question, the player just scores the normal points (Box 1).
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DISCUSSION ChemKarta was played in an introductory-level organic chemistry class of 15 students. During the game, students were encouraged to discuss among themselves to foster peer-to-peer B
DOI: 10.1021/ed500729v J. Chem. Educ. XXXX, XXX, XXX−XXX
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because of its novelty, its informal nature, simple design, and the ease of play. They described the game as constantly engaging because of the possibility of “stealing” another player’s points. Students felt that the game was dynamic and interesting because different Solution cards could be used to answer a Problem card. They thought the game was easier to learn by watching others play, rather than having it described to them. The card set was employed as a resource for classroom discussion and exam material. Molecules directly from the game were selected as exam questions for functional group identification. With 100 cards in the set, it was impossible for students to memorize answers, thus, requiring them to learn how to work through questions. The molecules from this card set were revisited in later sections of the course to provide familiar context to new material.
Box 2. A Complex Turn On his turn, Jacob reveals an amide Problem card (requiring identification of an amide group). He plays the Solution card Raspberry Ketone and incorrectly chooses a ketone. He discards his card and asks if any other players want to answer. Both Courtney and Lucas want to answer. Jacob chooses Lucas to answer. Lucas chooses the Solution card Stepronin, identifies the amide, and correctly answers the Honors question (linear) for 15 points. He also collects the Bonus card Thiophene (10 points) for playing a card with a thiophene group, for a total of 25 points. At the end of his turn, Jacob draws a card to replace the one he lost (Figure 2).
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learning. They would work together to help others solve Problem cards, explain answers, and encourage students who were struggling. Group cooperation was regularly observed at the beginning of the game, but as the game progressed, students who were winning would receive less help. Ultimately, in order to win, students’ peers required them to solve problems on their own. Formal evaluation of ChemKarta has yet to be conducted; however, student response was investigated through informal discussion and a pilot survey. Students said they liked the game
FUTURE WORK Comparative studies of this learning method versus traditional teaching techniques with a larger student population are still required. Further modification of the core game is being explored (e.g., adding cards that allow a player to draw more cards or search for a particular card). Additional content is being adapted into ChemKarta sets to cover more topics in undergraduate organic chemistry and at the graduate level.
Figure 2. A Complex turn: A player steals a Problem card and collects a Bonus card as well. C
DOI: 10.1021/ed500729v J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
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Activity
ASSOCIATED CONTENT
S Supporting Information *
A Solution deck (100 cards); Problem deck (48 cards); and Bonus deck (8 cards). This material is available via the Internet at http://pubs.acs.org.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Present Address †
Department of Chemistry, University of Missouri Kansas City, Kansas City, Missouri 64110, United States. Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS The author would like to thank Steven Bullock for his support of this project, the students of Midland University and College of Saint Mary for their input during development, and Dan Sullivan, Amar Natarajan, and Kaleb Michaud for their advice and critiques.
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DOI: 10.1021/ed500729v J. Chem. Educ. XXXX, XXX, XXX−XXX
