Engaging Organic Chemistry Students Using ChemDraw for iPad

Jun 23, 2015 - Chemoinformatics; Computer-Based Learning; Hands-On .... ChemDraw for iPad was also used to make a game where a student who submitted t...
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Technology Report pubs.acs.org/jchemeduc

Engaging Organic Chemistry Students Using ChemDraw for iPad Layne A. Morsch*,† and Michael Lewis*,‡ †

Department of Chemistry, University of Illinois Springfield, Springfield, Illinois 62703, United States Department of Chemistry, Saint Louis University, St. Louis, Missouri 63103, United States

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ABSTRACT: Drawing structures, mechanisms, and syntheses is a vital part of success in organic chemistry courses. ChemDraw for iPad has been used to increase classroom experiences in the preparation of high quality chemical drawings. The embedded Flick-to-Share allows for simple, real-time exchange of ChemDraw documents. ChemDraw for iPad also allows documents to be readily shared with students via e-mail directly from the program. ChemDraw for iPad increased engagement and enhanced interactions between students and instructors in organic chemistry classes.

KEYWORDS: Second-Year Undergraduate, Chemoinformatics, Organic Chemistry, Computer-Based Learning, Hands-On Learning/Manipulatives, Problem Solving/Decision Making, Reactions, Synthesis

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hile incorporation of a wide variety of technologies to teach organic chemistry continues to be an important subject of discussion,1−3 the incorporation of iPads is just beginning to be reported. iPads have been used to enhance content delivery4−6 and to improve student understanding of chemistry.7−11 Incorporation of chemical drawing tools into organic chemistry have great potential to improve student learning.12−14 The ability for students to draw structures, reactions, mechanisms, and syntheses correctly is of central importance to success in organic chemistry courses. ChemDraw for iPad has been used in organic chemistry courses at the University of IllinoisSpringfield (UIS) and Saint Louis University (SLU) to enhance that experience and to increase engagement with students during lecture classes.

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CHEMDRAW FOR iPAD ChemDraw for iPad (Figure 1) is a touch version of the desktop software that has been the industry standard for chemical drawing since 1985. It has a subset of the tools available in the desktop version along with some added functionality that is specific to the iPad. Structures can be drawn bond by bond or by using predefined rings or templates. Templates are included for a series of bicyclic compounds, as well as for common stereochemical drawings including Newman projections, sawhorse structures, Fischer projections, and common representations of 5- and 6-membered rings.

Figure 1. ChemDraw for iPad drawing of an SN2 mechanism. Contains PerkinElmer, Inc. copyrighted material. Printed with permission. All Rights Reserved.

the send icon pulls up a list of potential destinations for the drawing that includes Flick-to-Share (along with Mail, Dropbox, Twitter, Facebook, and Photos). The file can be shared with individual users or groups, or registered users that are included in the contacts within the Flick-to-Share Web site. In class, an instructor may “flick” a question or unfinished reaction to an entire class at once. Students can “flick” an answer back to the instructor.

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FLICK-TO-SHARE One of the most useful innovations for ChemDraw for iPad is the embedded Flick-to-Share function (Figure 2). Flick-toShare allows for exchange of any ChemDraw document with other individuals. Once a structure or reaction is drawn, tapping © XXXX American Chemical Society and Division of Chemical Education, Inc.

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DOI: 10.1021/acs.jchemed.5b00054 J. Chem. Educ. XXXX, XXX, XXX−XXX

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documents even if they do not have a desktop version of ChemDraw. It also allows them to share their work with others that may not have ChemDraw at all. Images of the drawings can also be sent to Twitter or Facebook directly to share publicly.

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USING CHEMDRAW FOR iPAD IN ORGANIC LECTURE ChemDraw for iPad was made available to test as a pilot at UIS and SLU in the summer of 2013. Examples of its use are the following (the original question is in black, while an example of a student response is in red) (Figure 3). Student instructions are shown below each question type.

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CLASSROOM METHODS

University of IllinoisSpringfield

ChemDraw for iPad has been employed in several ways during the five terms that it has been used in class (from summer 2013 through fall 2014) at UIS. Most of these methods continue to be used on a regular basis, while others have been discontinued. All of these were tested with each student having an iPad in classes of 18−45 students. During the pilot testing, iPads were loaned to the students to take with them for the duration of the semester. In subsequent classes, the iPad was a required element for the course. During the year prior to adopting ChemDraw for iPad, when iPads were first employed in introductory organic chemistry and the instructor walked around the room, it became apparent that, when students were

Figure 2. Flick-to-Share action screen. The drawing to be shared is shown in the middle, while there are three bars that show potential recipients at the top, left and right. Swiping your finger from the middle toward one of the bars sends the file to that person or group. Contains PerkinElmer, Inc. copyrighted material. Printed with permission. All Rights Reserved.

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INFORMATION SHARING In addition to the Flick-to-Share capabilities, users also have options to e-mail files in CDXML, .pdf, and .png formats. This allows students to embed their drawings directly into other

Figure 3. ChemDraw for iPad used for several different types of organic chemistry lecture problems: drawing reaction products (A), drawing reaction mechanisms (B), drawing molecular orbitals (C), and retrosynthetic analysis (D). Contains PerkinElmer, Inc. copyrighted material. Printed with permission. All Rights Reserved. B

DOI: 10.1021/acs.jchemed.5b00054 J. Chem. Educ. XXXX, XXX, XXX−XXX

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given time to work on a problem in class, only about half of the students in class would participate. The other half of the students waited to copy the instructor’s answer to the problem. By using Flick-to-Share and giving students two points per class period for submitting their responses to in-class problems, student participation increased to 100% engagement in problem solving during class. Students were awarded points whether they submitted a fully correct response or one with errors in it, and it was posited that, by attempting to solve the problem, students could engage in self-assessment. If the problem was answered correctly, students already understood the related material, while an incorrect response showed areas that needed to be reinforced. This self-assessment opportunity was previously missing for students that did not attempt in-class problems. During the first semester that ChemDraw for iPad was used, two questions for each of the first two exams were answered using ChemDraw and submitted via Flick-to-Share. Once a student submitted responses, a paper copy of the remaining exam was given to the student that had a blank space at the top of the exam for feedback and grades on the ChemDraw portion of the exam. Using ChemDraw for iPad on exams was discontinued because, eventually, students learned that they could use Flick-to-Share to send files to one another, as well as to the instructor. When several students stated their desire to use ChemDraw for iPad while studying, it was quickly realized that it was better to leverage the Flick-to-Share capabilities by having students use it to engage in group studying than to use it for exams. ChemDraw for iPad was also used to make a game where a student who submitted the correct answer to a problem the fastest won a small prize (e.g., a candy bar). This game was an unexpected positive learning opportunity, as often the first answer submitted was not correct, which permitted a discussion with the class why the answer was not completely right. This allowed the instructor and students to correct common misconceptions quickly and help students with their problem solving skills.

students reported thinking the app contributed to their overall learning experience.

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SUMMARY While ChemDraw has been a staple of chemical education and practice for years, ChemDraw for iPad brings new possibilities to the way it can be used in the classroom and, in particular, how it can engage students in problem solving during class. ChemDraw for iPad is available in the app store ($9.99)15 and is included in academic site licenses.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The authors thank PerkinElmer for the iPads lent to all students taking organic chemistry during summer 2013 at UIS and SLU. In particular, the authors thank Hans Keil and Phil McHale of PerkinElmer for their constant support of this initiative. The authors also thank the students from the Organic Chemistry courses at UIS and SLU for pilot-testing ChemDraw for iPad and giving extremely useful critiques. Finally, L.A.M. thanks Scott Schaus (Boston University) for the in-class game idea.

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REFERENCES

(1) Seery, M. K. Harnessing Technology in Chemistry Education. New Dir. 2013, 9 (1), 77−86. (2) Ryan, B. J. Line up, Line up: Using Technology To Align and Enhance Peer Learning and Assessment in a Student Centred Foundation Organic Chemistry Module. Chem. Educ. Res. Pract. 2013, 14 (3), 229−238. (3) Williams, D. P.; Bird, T.; Davies, D. L. Multimedia Resources for Teaching Chemistry. New Dir. 2013, 9 (1), 18−23. (4) Karatjas, A. G. Use of iSpartan in Teaching Organic Spectroscopy. J. Chem. Educ. 2014, 91 (6), 937−938. (5) Silverberg, L. J. Use of Doceri Software for iPad in Polycom and Resident Instruction Chemistry Classes. J. Chem. Educ. 2013, 90 (8), 1087−1089. (6) Silverberg, L. J.; Tierney, J.; Bodek, M. J. Use of Doceri Software for iPad in Online Delivery of Chemistry Content. J. Chem. Educ. 2014, 91 (11), 1999−2001. (7) Hesser, T. L.; Schwartz, P. M. iPads in the Science Laboratory: Experience in Designing and Implementing a Paperless Chemistry Laboratory Course. J. STEM Educ.: Innovations Res. 2013, 14 (2), 5−9. (8) Schwartz, P. M.; Lepore, D. M.; Morneau, B. N.; Barratt, C. Demonstrating Optical Activity Using an iPad. J. Chem. Educ. 2011, 88 (12), 1692−1693. (9) Amick, A. W.; Cross, N. An Almost Paperless Organic Chemistry Course with the Use of iPads. J. Chem. Educ. 2014, 91 (5), 753−756. (10) McCollum, B. M.; Regier, L.; Leong, J.; Simpson, S.; Sterner, S. The Effects of Using Touch-Screen Devices on Students’ Molecular Visualization and Representational Competence Skills. J. Chem. Educ. 2014, 91 (11), 1810−1817. (11) Bryfczynski, S. P.; Brown, R.; Hester, J.; Herrmann, A.; Koch, D. L.; Cooper, M. M.; Grove, N. P. uRespond: iPad as Interactive, Personal Response System. J. Chem. Educ. 2014, 91 (3), 357−363. (12) Flynn, A. B.; Caron, J.; Laroche, J.; Daviau-Duguay, M.; Marcoux, C.; Richard, G. Nomenclature101.com: A Free, StudentDriven Organic Chemistry Novenclature Learning Tool. J. Chem. Educ. 2014, 91 (11), 1855−1859.

Saint Louis University

ChemDraw for iPad was employed in a similar fashion at SLU during the summer of 2013 when it was pilot-tested in the second semester of an introductory organic chemistry course. The class met 2.5 h per day, 4 days per week for 4 weeks, and students were given either two or three iPad questions per class at random times during the period. Students received 0.5 extra credit points for each question, and a total of 37 questions were given during the course. A total of 780 points were available in the course, and thus, the iPad questions were worth slightly more than 2% of the grade. Points were earned simply for submitting an answer; answers were not graded for correctness. The e-mail feature of ChemDraw for iPad was used to share documents with students rather than Flick-to-Share. Students were e-mailed a question and given time to work the problem and to e-mail an answer back to the instructor. There was generally complete participation of all students in the class, and the instructor looked for an answer that highlighted a common problem the class was having understanding the material. This allowed for a discussion on how to arrive at the correct answer. The reception by the class to using ChemDraw for iPad was very positive. Student attendance was much higher than in the same summer course taught the previous year (2012), and C

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(13) O’Sullivan, T. P.; Hargaden, G. C. Using Structure-Based Organic Chemistry Online Tutorials with Automated Correction for Student Practice and Review. J. Chem. Educ. 2014, 91 (11), 1851− 1854. (14) Esteb, J. J.; McNulty, L. M.; Magers, J.; Morgan, P.; Wilson, A. M. Technology for the Organic Chemist: Three Exploratory Modules. J. Chem. Educ. 2010, 87 (10), 1074−1077. (15) ChemDraw for iPad. https://itunes.apple.com/us/app/ chemdraw/id631620841?mt=8 (accessed Mar 2015).

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