New Approaches to Games for Learning Organic Chemistry

Bradley, J.-C.; Lucci, A. and Thaker, Y.

Drexel University, Department of Chemistry, 32nd and Chestnut Streets, Philadelphia, PA 19104 (bradlejc@drexel.edu)


We report on the implementation of two gaming strategies to catalyze the learning of organic chemistry. The first game, "Wheel of Orgo", involves play in a face-to-face classroom context. Students take turns drawing reactions on a tablet PC to complete a multi-step synthesis. In the second game, "OrgoFrag", students explore a map within a First Person Shooter (FPS) environment (Unreal Tournament). The rooms are decorated with organic chemistry concepts and reactions on the walls and doors. Knowledge of the material allows for safe navigation through the map. The game can be played either alone as a maze or against bots and other players in Death Match mode.

Games in Organic Chemistry

Multi-step organic synthesis is a skill that many students find difficult to master. Discovering a chemically plausible path from a starting compound to a target product can involve considerable trial and error. It requires practice to develop the necessary skills.

Organic synthesis has been compared to chess (Todd 2005). In both cases, the combination of possible steps leads to very large possibility spaces. As a consequence, winning is likely to involve the application of successful strategies. In the case of chess, winning consists in defeating an opponent. In organic synthesis, a better strategy leads to a superior synthesis in terms of number of steps, avoiding side products, cost of materials, difficulty in purification, etc.

With this perspective, it should not be surprising that some students will spontaneously attempt to design syntheses for the fun of it. However, from the experience of one of the authors (JCB) in teaching organic chemistry for several years, very few students take this approach. This may be the case because skill and challenge must be commensurate for play to spontaneously occur.(Csikszentmihalyi 1975) For most students, the challenge of a multi-step synthesis surpasses their burgeoning skills. Instead of leading to a flow state conducive to play, frustration and discouragement are more likely.

Games have the potential to adjust the level of challenge by controlling the player possibility space (Prensky 2001, Raybourn 1997). Clear rules remove the ambiguities of real-world learning and enable a player to obtain immediate and frequent rewards. One approach to the implementation of games in organic chemistry involves a modification of the quiz format. Jeopardy! (Grabowski and Price 2003) and Millionaire versions of organic quizzes are examples of this. These games can be played as an aid to a face-to-face class or on a computer. Another example is a card game with products and reagents on the cards.

In this report we describe two additional games that can be played to help learn organic chemistry: Wheel of Orgo and OrgoFrag.

Wheel of Orgo

The Rules

The moderator selects a reactant and product and draws them on opposite ends of the chalkboard or tablet PC. Students then take turns drawing either a single step from the starting material or to the product. If the moderator determines that the transformation is chemically plausible, the student gets a point. Other students may then branch off from the new intermediates on the board. If the transformation is not feasible, the moderator blocks off that branch with a red X on the reaction arrow. Students may pass their turn. The student who places the final step that completes the synthesis is awarded 3 points. After a set time has elapsed (usually 30-60 minutes), the student with the most points wins. Figure 1 shows a screenshot of a completed game.


Wheel of Orgo was originally played on a chalkboard several years ago. Recently, the game was adapted to a tablet PC with a projector. Although some students who had never used a tablet PC were initially hesitant, all were able to adapt within the first session to draw out their synthetic steps without much assistance from the moderator. The tablet PC has one important advantage over the chalkboard: game sessions can be recorded using screen capture technology such as TechSmith's Camtasia, as exemplified in our Organic Chemistry III Class. This is useful for students to review their mistakes after the game and to give students who did not attend some of the benefits of the experience. The screen recording can be paused while the moderator gives students some time to think during their turn.

The role of the moderator is to ensure progress in the game and optimize the student experience. If too many students are passing their turn, the moderator can give hints or even draw a step to unblock the game. Although the game could be played without notes, having the students use their notes to find a reaction to use is a great opportunity to guide students in how to keep and use notes. If too many students are still passing their turn, another option is to count even incorrect attempts for a point, while correcting the entry and explaining the mistake. Finally the moderator may simply switch to an easier synthesis. A good choice for a synthetic target is a simple molecule with which the students are familiar (e.g. ibuprofen, DEET, aspirin).

A prize can also be given to the winner. Usually a nominal reward of $5 is given, which seems to motivate some students but not others. Some students who have won did not want the prize. Based on this experience, it may be more appropriate to offer a small mystery prize to the winner. This may also attract more students to play.


Wheel of Orgo can be an effective way to stimulate the interest of students in a face to face recitation session. This was made particularly evident during a class that started out as a traditional problem solving session and midway switched to the game. The material covered was the same; however, students that did not volunteer to answer any questions in the first half of the class eagerly participated in the game.

The role of the moderator is very important. If the level of assistance is insufficient, students will feel frustrated and stop participating. Conversely, if too much help is given or the reaction is easy, the better students will lose interest. In fact, if the distribution of skill between the players is too large, it can become difficult to have a game where everyone benefits equally. In such circumstances, it may better to separate the class into smaller groups where the participants are at a similar proficiency level.

FPS Games in Education

First Person Shooter (FPS) games are attractive for educational applications on several levels. The 3D environment presents an immersive experience for the player, thus enhancing engagement. The interface has commonly been experienced by many students and thus offers a certain familiarity. Also very sophisticated and intuitive game editors are available to encourage modification of these games (modding), usually by the creation of maps. A significant component of the success of these games derives from the modding communities that continually generate sometimes very elaborate playing environments that are optimized for playability.

Unreal Tournament (UT) is a good example of a FPS game with all the aforementioned advantages. Indeed, several educational application that make good use of UT's 3D rendering capabilities have been described, including a virtual museum (Nakamura), a virtual Audubon exhibit using the immersive Virtual Reality CaveUT system (Jacobson 2005a), a virtual Egyptian Temple (Jacobson 2005b) and a robot simulation arena (Wang). Ghostwriter makes use of UT script to assist students in creative writing projects by facilitating role playing (Robertson and Good). eScape enables the study of collaborative problem solving (Manninen and Korva). Voice recognition is also being incorporated to teach Arabic and to train soldiers for social interaction with Iraqis (Jaffe 2005).

Since the target users of these games are generally children and young adolescents, one of the key modifications involves the removal of weapons and violent interactions. Applications involving military training may introduce special weapons as an integral part of the learning exercise. Black Hawk Down represents such an application of UT (Silverman 2003). The same strategy of removing weapons for educational applications is common in other FPS games, with a few exceptions. Games2Train's Monkey Wrench Conspiracy (Prensky 2001) teaches the use of a 3D software design product. Military training applications with weapons involving FPS games besides UT have also been reported (Lindoff and Hasewinkel 2004).

FPS games have been also been used as vehicles to administer quizzes. As mentioned in a recent review of educational gaming (Downes 2005), an early application of this concept was implemented for a computer science class at West Point (Carver 1996) using the Doom engine. Students would answer questions by firing their weapon. A correct answer would enable them to continue exploring the map, while an incorrect answer would spawn monsters that they would have to fight. VR-ENGAGE, a geography quiz-based game also made use of a Doom-style interface, but did not include weapons(Virvou et al. 2002).


The approach that we took in incorporating organic chemistry into UT is most similar to the West Point example. Instead of substituting the game play with pedagogical objectives, we have retained the gameplay and incorporated the domain specific learning into the navigation of the maps. We make use of the editor that accompanies the standard commercial version of UT2004. The content that we include is incorporated completely in the maps that can be created with the editor. Compared with building a game on top of the engine, this is a much faster process. Another benefit is that the game is immediately playable online with any other UT2004 player. Of the aforementioned examples, only the virtual Egyptian temple is available as a downloadable map that can be played on the commercial version of UT2004.

A typical EduFrag map consists of rooms interconnected with hallways. Chemistry statements or reactions are drawn on the doors connecting the rooms. Walking through a correct door allows access to another part of the map leading sometimes to power-ups, health ammunition or other weapons. Walking through an incorrect door leads to death by falling into a deep dark pit. The player then respawns in or near a "study room" with class notes posted on the walls.

We have looked at 2 basic design strategies to convert an existing quiz into a UT map. The simplest is to copy the quiz question exactly as it appears in the regular quiz with a different option selected on each door in a room. As a result, students can consider the WebCT or UT quizzes to be interchangeable means of studying. (Figure 2) Another approach is to create concise true or false statements or graphical representations of reactions based on the quiz questions. (Figure 3) The advantage of this method is that decisions can be made much more quickly, which is important when in multi-player mode.

Creating maps from quizzes

The simplest way to create an OrgoFrag (or in general an EduFrag) map is to use a template. We have created a 10 question and 4 options per question template map with sequential navigation from the first question to the last. As a result, virtually any multiple choice test can be converted to a playable map.

First the map and textures of the template need to be downloaded. The most current map templates will be listed in the EduFrag wiki. Running Unreal Editor (UEd) 3.0 (comes with the installation of UT2004) then opening the template map will reveal its 3D layout. Green and red doors represent the target positions of correct and incorrect answers, respectively.

The images to be placed over the doors must be 256 x 256 pixel bitmap files with 256 colors. Text only questions can be prepared easily using Paint on a Windows system. For the drawing of chemical structures, the freely available ChemSketch can be used to generate the structures, which can then be pasted in Paint. The bitmap image is then imported into a texture file using UEd then clicking on the green or red door in the 3D view will insert the image.

Details of all these steps are available as screencast tutorials on the EduFrag wiki.

Future directions

Two UT organic chemistry maps (Lewis structures and alkynes) are currently running on our EduFrag server over the Internet and are accessible to everyone. We will investigate if educational UT maps can be made playable enough to sustain communities of chemistry students from around the world. Additionally, we will arrange for guided tours where faculty can meet with students during cease-fire to explain the notes posted in the study room, and to walk through the map discussing the chemistry behind the various questions on the doors. The chat feature of UT in combination with the ability to walk in front of reactions on the walls or individual students makes this convenient.


Carver, A. and Gregory, J. 1996. Enhancing Cooperative Learning Through Gamed-based Software, Proceedings of the World Conference in Educational Multimedia, ED-Media 96.

Csikszentmihalyi, M. 1975. Beyond boredom and anxiety: The experience of play in work and games. San Francisco, CA: Jossey-Bass.

Downes, S. 2005. Places to Go: Apolyton. Innovate 1 (6). http://www.innovateonline.info/index.php?view=article&id=198 (accessed August 24, 2005).

Grabowski, J. J. and M. L. Price. 2003. Simple HTML Templates for Creating Science Oriented Jeopardy! Games for Active Learning. Journal of Chemical Education 80: 967. http://chemed.chem.pitt.edu/joeg/documents/Jeopardy.pdf (accessed August 17, 2005)

Lindoff, J and Hasewinkel, H. 2004. Warfare Training with Game Consoles: Training without Getting your Hands Dirty! Paper presented at the Second Sweedish-American Workshop on Modeling and Simulation. http://www.mind.foi.se/SAWMAS/SAWMAS-2004/Papers/P19-SAWMAS-2004-J-Lindoff.pdf (accessed August 23, 2005)

Jacobson, J., Kelley, M., Ellis, S., Seethaler, L. 2005a. Immersive Displays for Education Using CaveUT. World Conference on Educational Multimedia Hypermedia & Telecommunications, Montreal, Canada, June 27-July 2. http://planetjeff.net/IndexDownloads/Jacobson2005c.pdf (accessed August 17, 2005)

Jacobson, J. and Holden, L. 2005b. The Virtual Egyptian Temple. World Conference on Educational Media, Hypermedia & Telecommunications (ED-MEDIA), Montreal, Canada. http://planetjeff.net/IndexDownloads/Jacobson2005e.pdf (accessed August 23, 2005)

Jaffe, I. 2005. A Virtual Course in Iraqi Arabic. All Things Considered, February 17, 2005. http://www.npr.org/templates/story/story.php?storyId=4503426 (accessed August 24, 2005)

Manninen, T., and T. Korva. Designing Puzzles for Collaborative Gaming Experience - CASE: eScape. Paper presented at the DiGRA 2005 Conference: Changing Views - Worlds in Play, Vancouver, British Columbia, Canada, May.

Nakamura, R. et al. A Practical Study on the Usage of a Commercial Game Engine for the Development of Educational Games. http://www.pcs.usp.br/~interlab/artigos/Wjogos03-Interlab-UT.pdf (accessed August 17, 2005)

Prensky, M. 2001. Digital Game-Based Learning. New York, NY: McGraw-Hill.

Raybourn, E.M. 1997. Computer Game Design: New Directions for Intercultural Simulation. Developments in Business Simulation and Experiential Exercises 24. http://www.cs.unm.edu/~raybourn/games.html (accessed August 17, 2005)

Robertson, J., and J. Good. Ghostwriter: A narrative virtual environment for children. http://homepages.inf.ed.ac.uk/judyr/publications/idc2003.pdf (accessed August 17, 2005)

Silverman, B. G. et al. 2003. Authoring Edutainment Stories for Online Players (AESOP): Introducing Gameplay into Interactive Dramas. Paper presented at the International Conference on Virtual Storytelling. **http://www.seas.upenn.edu/~barryg/heart/publ/AESOP-ICVS.pdf** (accessed August 23, 2005)

Todd, M. H. 2005. Computer-Aided Organic Synthesis. Chemical Society Review 34: 247.

Virvou, M. et al. 2002. VR-ENGAGE: A Virtual Reality EducationalGame that Incorporates Intelligence. Paper presented at the IEEE International Conference on Advanced Learning Technologies. http://lttf.ieee.org/icalt2002/proceedings/t1303_icalt063_End.pdf (accessed August 23, 2005)

Wang, J. USARSim: A Game-based Simulation of the NIST Reference Arena. http://usl.sis.pitt.edu/ulab/USARsim_manual.pdf (accessed August 17, 2005)