Teaching Classes of Organic Compounds with a Sticky Note on

Activity pubs.acs.org/jchemeduc

Teaching Classes of Organic Compounds with a Sticky Note on Forehead Game Kevin P. O’Halloran* School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, Georgia 30043, United States S Supporting Information *

ABSTRACT: An in-class game has been developed to teach students the classes of organic compounds that arise from the common functional groups in organic chemistry. The rules are simple and straightforward and are already familiar to students because they are based on a popular party game. All of the students have either the structure or name of an unknown class of compound written on a sticky note that they place on their foreheads. The objective is for each student to figure out what his or her molecule is by asking other students a series of provided questions. The game is a fun alternative to rote memorization or using flash cards. The strategy is effective because it requires students to think about these molecules through discussion, especially their similarities and differences. I call it The Organic Compound Name Game.

KEYWORDS: Organic Chemistry, Hands-On Learning/Manipulatives, Humor/Puzzles/Games, First-Year Undergraduate/General, Second-Year Undergraduate, Molecular Properties/Structure

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INTRODUCTION When students first learn about functional groups and classes of organic compounds in a typical course, they are usually told to memorize them from the book at home. Instead of that approach, presented here is a method of teaching that helps students learn them during class rather than outside of class. This method is an adaptation of a common party game where each participant has a sticky note on their forehead with the name of a famous person written on it. Then, each participant asks other people yes/no questions in order to determine who is written on his or her sticky note. That party game has slight variations and goes by several different names including The Name Game, Sticky Head Game, Who Am I Game, and Forehead Detective. Since this adaptation of that game is applied to classes of organic compounds, I refer to it as The Organic Compound Name Game. The major modifications are that (1) students either have the name or structure of a class of compound written on his or her sticky note, and (2) students are given a list of yes/no questions to ask other participants. To the best of my knowledge, this is the first report which adapts this common game to teach a science topic in the classroom. The premise of the game is depicted in Figure 1. Sticky notes, or Post-it notes, have been used in a few innovative ways for teaching science topics in class. Flynn used sticky notes to teach students how to build a molecule from NMR and IR spectra by writing molecular components, like CH2, on sticky notes.1 Sticky notes, along with other paper and plastic items, were used to teach medical doctors the shape of the pharyngeal flap and sphincter pharyngoplasty2 and a © XXXX American Chemical Society and Division of Chemical Education, Inc.

Figure 1. Objective of the game is to determine the class of compound written on your sticky note.

medical procedure for palate repair in children called Furlow palatoplasty.3 Sticky notes have been used in the Slip Method of brainstorming and paired with a priority-payoff matrix for nursing students.4 A traditional strategy for learning classes of organic compounds is flash cards. In a departure from that strategy, a Received: February 26, 2017 Revised: July 31, 2017

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DOI: 10.1021/acs.jchemed.7b00165 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

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few creative ways to teach this material have been reported. A matching card game called ChemKarta was developed by Knudtson.5 Byrd developed a method of having students develop a classification key to categorize the classes of compounds based on similarities.6 The Royal Society of Chemistry hosts an online matching game for classes of compounds.7 The purpose of this paper is to describe an in-class game for students to learn the classes of organic compounds that arise from common functional groups. The intended audience is the first semester of organic chemistry, or other courses where this material is first introduced. Table 1 shows 12 classes of organic compounds and their names which are used for a class of 24 students. For much larger courses it may be more feasible to do as a laboratory activity. The group “R” can represent either a carbon or hydrogen atom.

Table 1. Classes of Organic Compounds Selected for This Game

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THE ACTIVITY Game play begins with the instructor passing out a sticky note to each student to place on his or her own forehead. It is important to tell the student to not look at what is written on the sticky note. The sticky notes can either be handed out individually or laid upside down on a front table for students to pick up. Students are also given the list of yes/no questions to ask (see Supporting Information). These questions ask about certain aspects of a class or compound, and each answer only gives one piece of information. Students usually cannot figure out their class of compound with only one question, but instead can figure them out on the basis of the information from multiple questions. Rules of the Game

These simple rules are provided on students’ sheets and allow them to quickly understand the game. • You can only ask the questions below. • You can only answer “yes” or “no” to each question. • Ask anyone one question, then let them ask you one question, and then move to on to another person. • Write down the first name of the person who answered your question. List of Yes/No Questions

These questions are provided on students’ sheets and serve to structure their discussion. 1. Does my molecule contain a double bond? 2. Does my molecule contain a triple bond? 3. Does my molecule contain one, and only one, oxygen atom? 4. Does my molecule contain two oxygen atoms? 5. Does my molecule contain one, and only one, R group as shown? 6. Does my molecule contain two or more R groups as shown? 7. Does my molecule contain nitrogen? Once everyone has a sticky note on their forehead and a list of yes/no questions, they are free to stand up, move around the classroom, and ask neighbors questions from the list. Once each student figures out what his or her molecule is, they will ask the instructor if they are correct. If they are correct, then they can move to the front of the room, dubbed “the winner’s circle”, and wait for the person with the corresponding molecule to find them. Two people in the class have a matching pair (name and structure), but they will not know who that person is until

they both figure out their molecule and find each other in the winner’s circle. They may have passed by that person and even asked them a question earlier in the game. The activity takes a class of 24 students about 20 minutes to complete their first time. This activity has been used successfully in many of my courses over the past several years. The game can easily be scaled up to larger class sizes with the duplication of some molecules on this list, or scaled down to smaller classes by removing some molecules from this list. The game works well B



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Figure 2. Class environment during the game involves structured discussion and collaborative problem solving.

There are a few other advantages. For pedagogy, it makes students think about similarities and differences of classes of compounds (i.e., alcohols and ethers both have one oxygen, but ethers have two R groups while alcohols only have one R group). As a result, students start to categorize these molecules in their minds as they play the game. Another advantage is that students can learn the material in a class period, whereas if students are asked to go home and learn, it will likely take them a week to do so. The game is easy to play because students are already familiar with the original form of the game, and sticky notes are also cheap and scalable. Future work includes more chemistry games with sticky notes.

because it provides students with structured discussion that leads to collaborative problem solving as shown in Figure 2.

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INSTRUCTOR PREPARATION

Before class, one sticky note is prepared for each student. For a class of 24 students, 12 sticky notes contain structures and 12 sticky notes contain names of classes of organic compounds. Prepare the sticky notes by taking a fresh pack and drawing the structures or names on the center of a sticky note. Each note should be lifted and the stack maintained during this process in order to preserve the original stack. This makes carrying it to class very easy. Print a copy of the list of yes/no questions for each student (see Supporting Information). An optional step follows: If they have not had enough exposure to this material yet, then print the second page of the Supporting Information on the back page which has a list of possible classes of compounds. However, if students have had enough exposure to this material, then they can do the activity without a list. If students do not want to put the sticky note on their foreheads, then they can put it on their shirt collar as long as they cannot see it.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.7b00165. Worksheet for students that has the game rules, the list of yes/no questions, and a page (optional) that contains a list of possible classes of compounds (PDF, DOCX)

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DISCUSSION AND CONCLUSIONS It is an entirely different way of learning classes of organic compounds. The greatest advantage of this game is that it is fun for the students as an alternative to memorization. Rather than looking at them or writing them down, students here ask and are asked questions about their chemical makeup and bonding. This requires them to imagine the molecules in their minds. The educational benefit to the person answering the question is that when they are asked “Does my molecule contain a double bond?” and they see the word “alkene” written on that person’s forehead, they have to think about whether an alkene contains double bonds before they can answer. Students usually begin the game a bit perplexed, and then get more involved as curiosity sets in, and ultimately get excited when they figure out what their molecule is.

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Kevin P. O’Halloran: 0000-0003-2353-4825 Notes

The author declares no competing financial interest.

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REFERENCES

(1) Flynn, A. NMR Interpretation: Getting from Spectrum to Structure. J. Chem. Educ. 2012, 89 (9), 1210−1212. (2) Lee, J. J.; Jabbour, N. Teaching the Pharyngeal Flap and Sphincter Pharyngoplasty: The Sticky Note Method. Int. J. Pediatr. Otorhinolaryngol. 2015, 79 (11), 1905−1908.

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(3) Liu, M. M.; Kim, J.; Jabbour, N. Teaching Furlow palatoplasty: the sticky note method. Int. J. Pediatr. Otorhinolaryngol. 2014, 78 (11), 1849−1851. (4) Reeder, G. Take a Sticky Note on Brainstorming. Nurs. Manag. 2017, 48 (1), 32−37. (5) Knudtson, C. A. ChemKarta: A Card Game for Teaching Functional Groups in Undergraduate Organic Chemistry. J. Chem. Educ. 2015, 92 (9), 1514−1517. (6) Byrd, S.; Hildreth, D. P. Learning the Functional Groups: Keys to Success. J. Chem. Educ. 2001, 78 (10), 1355−1357. (7) Functional Groups: GridlocksCan You Unlock the Grid?. http://www.rsc.org/learn-chemistry/resources/gridlocks/puzzles/ level-3/functional-groups.html (accessed Jun 2017).

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Teaching Classes of Organic Compounds with a Sticky Note on

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