Activating Students' Interest and Participation in Lectures and Practical

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Activating Students’ Interest and Participation in Lectures and Practical Courses Using Their Electronic Devices Maikel Wijtmans,*,† Lisette van Rens,‡ and Jacqueline E. van Muijlwijk-Koezen† †

Section of Medicinal Chemistry, Amsterdam Institute for Molecules, Medicines and Systems, VU University Amsterdam, Amsterdam, The Netherlands ‡ Department of Research and Theory in Education, VU University Amsterdam, Amsterdam, The Netherlands S Supporting Information *

ABSTRACT: Interactive teaching with larger groups of students can be a challenge, but the use of mobile electronic devices by students (smartphones, tablets, laptops) can be used to improve classroom interaction. We have examined several types of tasks that can be electronically enacted in classes and practical courses using these devices: multiple choice (MC) questions; open-ended questions; and 3D visualization of (bio)molecules and complexes. We have introduced these tasks dynamically in several educational contexts in our teaching programs. Specifically, attention is paid to applying devices in introductory quizzes at the start of a course, throughout lectures, and in practical courses. Each application has been found by us to offer significant merits in terms of connecting theory and practice, full formative assessment (including an improvement in interactions of introverted students), monitoring progress, engaging students early on in research, stimulating “3D” molecular feeling, and maintaining student attention. From the student perspective, evaluations revealed overall positive feedback on several key aspects of our approaches. In all, we believe that this mutually beneficial way of teaching can be of broader application, also in nonchemistry-related curricula. KEYWORDS: First-Year Undergraduate/General, High School/Introductory Chemistry, Second-Year Undergraduate, Upper-Division Undergraduate, Internet/Web-Based Learning, Testing/Assessment, Medicinal Chemistry, Drugs/Pharmaceuticals, Molecular Modeling

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INTRODUCTION

in-class interaction in larger student groups using the portable devices (at that time: iPad tablets) of students. We have since learned how to embrace all types of devices that students may bring along, not only because our tablet loan program was stopped last year but also because some classes in previous years contained students from other programs without a tablet loan protocol. The range of devices nowadays includes laptops, smartphones, and tablets, all with varying operating systems. The power of smartphones in teaching has already been reported by others.4 Indeed, it is our belief that the current generation of students is comfortable with incorporating electronic devices into teaching, because information technology (IT) has become such an integral part of their lives. We report here on how we have increasingly used students’ electronic devices in our teaching programs during the past 3 years as a means to conduct formative assessments. Particular attention will be paid to using devices to conduct various types of “live” questions and to increase 3D molecular thinking about (bio)molecules and molecular complexes, as well as to embracing as many types of devices possible. While the presence of devices will require responsible behavior of students with respect to potential distraction (gaming, Facebook, Twitter, etc.), we intend to demonstrate how the

Interactive teaching is believed to stimulate deep learning with students.1 Indeed, a very recently published meta-analysis suggests that activated teaching methods are effective in a broader context.2 Asking questions, working on problems, and buzzing (short discussion activities to refresh the concentration span) are forms of interactive teaching. These specific interactive teaching methods work particularly well for teaching in smaller groups.3 Stimulating a deeper level of thinking in class with larger groups of students (50 or more students) remains a challenge, especially with respect to shy or less vocal students. The emergence of electronic tools and the increase in use of portable devices by students provide opportunities for inclass activating and can provide rapid and efficient ways to engage larger groups of students. Our Pharmaceutical Sciences bachelor and Drug Discovery and Safety master programs both address early drug research and place strong emphasis on the chemistry component. Prior to 2010, a pilot study run by one of us (J.E.v.M.-K.) demonstrated the successful use of physical clickers (Classroom Performance System, McGraw-Hill) or SMS (Short Message Service) voting in classrooms. Between 2010 and 2012, the department launched the Mobile Learning Initiative, in which first-year students were equipped with a loan iPad tablet. It was in this setting that we first initiated our efforts to increase the © XXXX American Chemical Society and Division of Chemical Education, Inc.

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teacher can turn the devices into powerful instant-activating tools in the classroom. We conceptually envisage our approaches so far as a matrix (Figure 1): the types of electronic tasks can be thought of as

Table 1. List of Explored Apps/Software and Brief Characteristicsa Name GoSoapBox Socrative iMolView Liteb NDKMol ESMol Jmol Molecules PyMol Chem3D Jmolb

Figure 1. Matrix representation of the use of electronic tasks in various educational contexts. The size of the symbol corresponds to the amount of our incorporation of the given task in the given educational context during our explorations.

GLMol

b

Operating system

Purpose

All (browserbased) All (browserbased) Android/iOS

MC/open-ended questions MC/open-ended questions 3D visualization

Android Android Android

3D visualization 3D visualization 3D visualization

iOS iOSc iOSc Windows/ Macintosh Windows/ Macintosh

3D 3D 3D 3D

visualization visualization visualization visualization

3D visualization

Database Source

PDB/Drugbank/ PubChemd PDB/PubChem PDB/PubChem PDB/PubChem or NCI/NIH resolver PDB/PubChem PDB/PubChem PDB PDB/PubChem or NCI/NIH resolver PDB/PubChem

a

The list was compiled in Nov 2013. bEmpirically defined by us as having proven most useful in terms of optimally broad use in our classroom. cAvailable for iPad, but (as of May 2014) not for iPhone. d PubChem source available as of May 2014.

being on the horizontal axis, whereas the educational contexts in which the tasks can be used should be envisioned on the vertical axis. The green symbols represent nodes which we have explored already, with the size of the symbol corresponding to the amount of our incorporation of the task in the educational context. It is up to the creativity of the teacher to explore any task in any context and perhaps expand the matrix with new rows, columns, and nodes. As an extension, we hope that Figure 1 also conveys the message that the advantageous use of mobile devices is not confined to chemistry curricula.

the highest and disclose a basic tutorial for this app. For laptops, Jmol10 has proven to be an efficient tool because it too can handle small molecules and PDB structures. We refer to the Supporting Information for more details on these key apps/ programs.

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TYPES OF ELECTRONIC TASKS Figure 1 illustrates the types of in-class electronic tasks that were used and monitored. These will be discussed in detail below. Depending on the nature and difficulty of the task and educational context it is used for, a task took anywhere from 2 to approximately 10 min including feedback.

DEVICES AND SOFTWARE Several articles have addressed the use of chemistry and drug discovery apps for mobile devices.5−7 For our teaching purposes, all nodes in Figure 1 critically depend on the appropriate apps/software. Thus, one needs to take note of the most common devices in the classroom. In Sept 2013 in our classrooms, these were tablets (iOS/Android), smartphones (iOS/Android), and laptops (Windows/Macintosh). For all devices we found apps/software that were appropriate for the tasks shown in Figure 1. Table 1 shows an overview of apps/ software tested by us. The table was compiled in Nov 2013 and is based on experience gathered by us, although we do not wish to imply this list to be universally complete. Some 3D visualization apps have already individually been mentioned in teaching and research contexts,5,6 but aligning a full array of apps and operating systems with our intended goals had to our knowledge not been reported and required some time investment. Except for GoSoapBox, for which the teacher may have to contribute a fee, all listed apps are free for use for students and teachers alike. In the table, we have indicated the apps/programs that we have found most useful in terms of optimally broad use in our classroom. For polling purposes, GoSoapBox8 is currently our preferred tool for several reasons. iMolView Lite has been our app of choice for in-class 3D visualization on smartphones and tablets, because (1) it is available for both Android and iOS devices and (2) it is able to visualize both small molecules and PDB structures. Interestingly, a very recent review on apps for visualizing PDB structures on iOS and Android devices covers many of the apps we had explored over time.9 The authors also rank iMolView

Multiple Choice (MC) Questions

The use of MC questions, also known as “polling” or IAQ (interactive anonymous quizzes), is a well-known concept in teaching as it gives teachers the opportunity to assess student understanding, prior knowledge, etc. Polling is classically based on, e.g., colored cards, physical clickers, or even thumbs.11 Eric Mazur and others have pioneered polling as a tool for formative assessment.12,13 The use of smartphones as modern clickers has previously been alluded to.14 Conceptually, by resorting to browser-based software one can engage virtually all types of devices in the classroom, not relying exclusively on smartphones. Toward this end, we have used the software program Socrative 1.015 and, more recently, GoSoapBox.8,16 Electronic polling equips the teacher with the known advantages of classical polling, such as getting insights in the progress of class material and providing students with a progression mirror. The anonymous character ensures a “safe” context17 and may encourage increased participation by introverted or insecure students. Accordingly, we often also introduce the answer “I do not know” to have an accurate overview. We allow students to discuss the question among each other before, and sometimes after, answering. This is related to the concept of Peer Instruction, which is suggested to improve understanding.18 We have noted how some students worked and answered as duos or even as teams and all at their B

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own pace, which is facilitated by the electronic character nature of the polling. When compared to physical clickers, electronic polling has several advantages: 1. No special physical preparations, such as obtaining physical clickers, are necessary. It provides a rapid and easy way to poll with equipment that is always around (i.e., devices). 2. Pictures and text can be shown on the devices along with the answer letters (A, B, etc.). We employ this to allow students to take a multiquestion quiz at their own pace (vide infra). For single questions, though, we prefer to have all textual answers/pictures listed on the plenary screen, with the devices merely showing the corresponding answer letters. 3. Polling results are visible in real time to the teacher on her/his device (an arbitrary illustration is shown in Figure 2A), which is a great asset for focused feedback and another step forward since the very early days where paper inspection was sometimes required.19 Using, e.g., GoSoapBox, a teacher can also enable the option of having results be visible in real time on a student’s device immediately af ter his/her submission is complete. This gives students an overview of their peers’ views while, importantly, an answer cannot be changed anymore (minimizing “copy-cat” behavior). Open-Ended Questions

Figure 2. (A) Screen capture of the responses on an arbitrary MC question using GoSoapBox. (B) Comparative results of a prospective question from an electronic introquiz in a first-year general chemistry course having taken place at the start of the first semester in three consecutive years (academic years 2011−2012, 2012−2013, and 2013−2014). The question involved (“Which salt is the most soluble?”) is referred to in the main text, while the format of this question, including possible answers, is shown in Figure S10 in the Supporting Information. The x-axis shows the 5 possible answers (A to E), while the y-axis shows the percentage of answers. Answer C is correct, while answer E is “I do not know”.

Some polling software, like GoSoapBox and Socrative, also allows for open-ended questions to be filled out rapidly and anonymously by students in class. Typically, a spreadsheet with all the answers immediately becomes available on device of the teacher, who can browse through the answers in real time or afterward. It is a unique protocol that clearly sets apart the use of devices from physical clickers. However, the best way to deal with the answers on open-ended questions is more complex and, for us, still a work in progress. It is evident that, for more focused feedback, in-class results would have to be inspected by the teacher at a later stage, bordering “grading”. In finding a balance between excessive grading time and effective use of open-ended questions, we realized that the mere fact that students can be triggered to think about a challenging or key question without prepared MC answers is a gain in itself. In line with this strategy, we have primarily used open-ended questions to conduct early “expectation management”/”pitfall awareness” among the students by having them think about important course aspects ahead of time. General feedback may be provided by the teacher after quickly inspecting the results in real time. Often, the anonymous results to an open-ended question were sent to the students as a PDF document after the class for optional viewing. For the teacher, the answers on open-ended questions provide a rich source of thoughts.

databases such as PubChem20 for small molecules, and the PDB database21,22 for biomolecules and complexes. The software allows rotating and zooming and as such provides students with an opportunity to get a “3D feeling” for molecular systems. Students are told that the downloaded structures still represent “static” depictions (X-ray, NMR, calculations, etc.) while molecules are much more dynamic in real life. By including recently published structures, students can also be familiarized with the key notion that chemical knowledge is continuously expanding, well beyond their textbooks. During many of the in-class 3D tasks, the variety of devices (and thus of required software) may be perceived by the teacher as technically somewhat demanding, but a good preparation by the teacher and clear instructions to the students greatly help. With the incorporation of Anaglyph stereo mode in certain apps/software for mobile devices (e.g., Jmol, iMolView Lite, ...), in the near future we plan to explore this feature in conjunction with inexpensive red-cyan 3D glasses to get an even more realistic 3D experience on the devices. The successful use of the Anaglyph stereo mode in teaching on nonmobile devices has previously been alluded to.23

3D Visualization

A more chemistry-specific task is 3D visualization, because small and large (bio)molecules and the interaction between these play important roles. It is paramount that the appreciation of the 3D structure of (bio)molecules and its role in chemistry and drug action must be triggered among students as early as possible. During some classes as early as first-year level, students are given small in-class tasks in which they need to inspect the 3D structures of relevant molecules or complexes. Structures are downloaded on the spot from freely accessible C

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3. “Which oxidation state is incorrect?” for the oxidation of methanol. On average, only 23% percent of students correctly identify that the C in CO2 is not +2, while on average 41% answer “I do not know”. The high percentage of “I do not know” or wrong answers on these prospective questions clearly confirms that the background knowledge on the topics is very limited. Students are ensured that the involved topics will be dealt with in detail throughout the course. Thus, an initial high amount of “I do not know” or wrong answers also demonstrates to students that many new topics will be dealt with in the course. As such, it contributes to phases 1 (task definition) and 2 (goal setting) of the four-stage model of motivation described by Winne and Hadwin.24 We regularly use open-ended questions in an introquiz for a course, since we think they can be very useful there to provoke thoughts on the contents of the course. Exemplary questions that we used in that respect are as follows: 1. “What do you think is the most difficult part of the course and why?” 2. “What do you think is the least difficult part of the course and why?” 3. “In previous runs of this course, we have seen teams which first did all the computational work and then proceeded to do the synthetic feasibility study in the very last days. Please comment on any pros and any cons of such an approach.” The collected anonymous results provide the teacher with a rich insight in the students’ thoughts and are later sent back to students for optional viewing.

APPLICATION OF ELECTRONIC TASKS IN EDUCATIONAL CHEMISTRY CONTEXTS Having defined key electronic tasks along the horizontal axis of the matrix (Figure 1), we proceed with showing detailed examples of the use of these tasks in various educational contexts, thus populating the vertical axis and nodes in Figure 1. Introquiz at the Start of a Course

An introquiz at the start of a course is a powerful way to assess prior knowledge so appropriate connections can be made between knowledge gained in previous classes and upcoming course content. This has most extensively been used at the start of a first-year general chemistry course, taking place at the very beginning of the first semester. We use a quiz with 15 MC questions and administer these during the first plenary gathering. A few ref lective questions were used, referring to “easier” questions on material that students should know already from high school and that is a stepping stone for the upcoming course. The answers on this summative part often have a high scoring percentage (see, e.g., Figures S1 and S2 in the Supporting Information). Importantly, we also deliberately incorporate prospective questions which deal with material that students have likely not seen before but that will be part of the upcoming course. Not surprisingly, such questions have proportionally high amounts of the “I do not know” answer and/or of wrong answers (see Figure 2B, and Figures S3 and S4 in the Supporting Information). For teachers, this setup gives the powerful opportunity to inspect the prior knowledge on the class material, which in this course is important given the influx of students from many different high schools, and at the same time provide students with a course overview. For students, it serves as an activating glimpse on the course contents and on their own prior knowledge. We have the answer histograms for each of these introductory questions return again when the involved material is dealt with (sometimes >1 month later) to confront students with their answers given at the start of the course (Figure S10B in the Supporting Information). Occasionally, we re-ask the question and thus have students inspect their progress in the course (Figure S9 in the Supporting Information). Interestingly, after 3 years of taking this introquiz with the same questions, we could compare the overall results per year allowing us to somewhat assess the yearly general level of student influx from high school (see Figure 2B, and Figures S1−S8 in the Supporting Information). Over 3 years, no major differences were noticed, suggesting that the level of knowledge from high school had remained roughly analogous. The power of the introquiz can be illustrated by using the 3-year statistics to pinpoint a few consistently notorious prospective questions. Three of these are as follows: 1. “Which salt is the most soluble?” accompanied by three Ksp values (solubility ion products in water) for salts having different numbers of ions. On average, only 12% percent of students correctly recognize that the number of ions plays a role, while on average 45% pick the salt with the highest Ksp value and 41% answer “I do not know how to determine this.” The results for this prospective question are shown in Figure 2B, while the format of the question is shown in Figure S10 (Supporting Information). 2. “What is the pH of a 1.0 · 10−8 M HI solution?” On average, only 15% of the students answer correctly while on average 45% answer “pH = 8.00”.

Lectures

During regular lectures, MC questions prove a powerful tool to activate students.13 Particularly, strategic questions can show teachers and students alike whether the material and concepts are grasped appreciably. We keep the amount of questions per lecture below four and select strategic time points based on the notion that these tasks can refresh the concentration span. An average concentration span for students being normally estimated to be ca. 20 min,25 it stands to reason to use ca. 20 min time points for interactive tasks. A unique application of polling is to engage the students in questions about chemical research. Toward this end, we have used literature research articles as well as our own (sometimes still unpublished) research. A MC question with several possible directions is posed and students are asked their opinion “as researchers”. This way, scientific chemistry research, which is often very abstract especially for first-year students, can be introduced very early on in a somewhat befriending manner. Four examples of used research-oriented questions are shown below. 1. “What precursor would you pursue as a researcher?” referring to the large-scale synthesis of the drug Tamiflu during which the researchers had to consider precursors other than quinic acid.26 2. “Which compound seems most interesting to test the halogen-bonding hypothesis?” referring to our own work in which evidence pointed toward an important role of a halogen atom in activation of the CXCR3 receptor by an organic ligand.27 3. “Which of the following proposed guests do you think will bind best?” referring to research based on host− D

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guest complexation between ferrocene and cucurbit[7]uril.28 Figure S11 (Supporting Information) shows the format of this question. 4. “What is your hypothesis?” concerning the mode of action of cisplatin and referring to research in which a crystal structure of a cisplatin-bound double-stranded DNA decamer was reported (vide infra).29 Regularly, 3D visualization tasks were applied during lectures, all accompanied by a task/question and tailored to the subject at hand that day. In a sense, this is formative assessment concerning “3D thinking”. Here, we list a few exemplary tasks: 1. “Are these two structures superimposable?” For historical reasons, the enantiomers of thalidomide are used for this purpose ((R)- and (S)-2-(2,6-dioxopiperidin-3-yl)-1Hisoindole-1,3(2H)-dione). Students were asked to work in pairs so as to be able to compare the involved structures on two screens by rotating etc. 2. “Is the orientation of the two phenyl rings in a biphenyl unit parallel?” The structures of the drugs losartan and flurbiprufen are used. 3. “Find the hydrogen bonds” concerning a small peptide with alpha-helices. PDB structure 1IYT is used.30 The format of this question is shown in Figure S12 (Supporting Information). 4. “Find the hydrogen bonds” concerning a pleated sheet. PDB structure 1SA8 is used.31 5. “Pinpoint the seven transmembrane helices in a G protein-coupled receptor”. PDB structure 3P0G is used.32 6. “Pinpoint the proposed halogen bond in a complex of a protein and an iodine-containing ligand”. PDB structure 2YJ8 is used.33 Open-ended questions were occasionally used in lectures. An interesting protocol is one in which 3D visualization and openended questions are combined. Illustrative is a research-based question concerning the drug cisplatin (vide supra). Students were asked to work in pairs and compare, in 3D on their devices, the crystal structures of two double-stranded DNA decamers, one without bound cisplatin (PDB 309D)34 and one with bound cisplatin (PDB 1A2E).29 Figures 3A−3C show screen captures of the latter on devices common among students. An accompanying research-oriented question on the mode of action of cisplatin (“What is your hypothesis?”) was answered in class as an open-ended question on their devices. Plenary feedback was then given, and the spreadsheet gave a broad overview of thoughts afterward. Figure S13 (Supporting Information) shows the format of this question.

Figure 3. Screen captures of 3D visualizations on devices, exemplified by use of PDB entry 1A2E (a complex consisting of cisplatin bound to a DNA decamer) on (A) a laptop using Jmol, (B) an Android tablet using iMolView Lite, and (C) an iOS tablet using Molecules.

Information for format). This ensures that students can take the quiz at their own pace. Quiz topics address safety, observations, theory, and mechanisms. In the basis, this method utilizes the “spacing effect” because tests are being administered at spaced intervals (usually 1 day).35 At the end of the month, a winner, having the highest score, is announced. To this end, the quiz is necessarily single blind (names are known to teachers but not to peers) and each question is graded with 1 (correct answer), −0.5 (incorrect answer) or 0 (“I do not know”). This grading scheme, of which the students were aware, was set up to facilitate a learning curve, i.e., discourage guessing yet not be too harsh on wrong answers. Exemplary questions are on carbocations when trityl alcohol is synthesized, on oxidation states when KMnO4 is used, on types of aromatic reactions when a nitration is performed, etc. Open-ended questions were used in practical courses as well. Most notably, a practical course can be started with a handful of

Practical Courses

Practical courses play a vital role in any chemistry- and/or drugoriented curriculum, because they aim to have students combine various learning goals such as technical skills, theory and concepts, planning, and reporting techniques. This combination of focus points sometimes diminishes the time students allow themselves to spend on correlating practice with theory. In an effort to stimulate this correlation, we have set up a daily quiz during a month-long full-time second-year practical course in organic chemistry. Every day starts with a plenary gathering during which a quiz is administered. This quiz is different every day and consists of 3 to 5 MC questions with associated text and pictures being shown on devices and not on the plenary screen (see Figure S14A,B in the Supporting E

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the quiz (using scores, bonus days, etc.) is deemed nice by students but not necessary per se to induce participation. As an important token to the activating character of this quiz, students acknowledge that the quiz causes them to think about things they consider relevant but would not have thought about themselves (Table S7 in the Supporting Information). Most notably, all closing evaluation statements (typically in the form of “These approaches should be done again next year and, where applicable, optimized”) are without exception answered with a strong “agree” (Table S1 in the Supporting Information), which we consider as a token of encouragement. It is also worth mentioning that the evaluations revealed that the transition from exclusively iPad tablets to various device types was not a problem (see Supporting Information for more details).

open-ended questions that, as discussed previously, aim to gather thoughts of students on the course itself and at the same time raise awareness of common pitfalls with respect to, e.g., planning responsibilities of students. Throughout the practical course, open-ended questions were also incorporated into the daily quiz to encourage students to ponder a research question related to their own experiments. One example of a format that was used for this purpose is shown in Figure S14C in the Supporting Information. An occasional 3D task was used to help in interpretation of a 1H NMR spectrum.

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EVALUATION

Teachers

Within our teaching programs in the last 3 years, a few teachers have been early adapters and have applied the electronic tasks outlined in this manuscript to varying extents. The application of MC questions in lectures (with smaller and larger groups) or practical courses (quiz) has been implemented most frequently. The consensus among involved teachers is that the electronic MC questions represent effective and easy-to-use tools for stimulating students to ponder topics relevant to the course and for obtaining snapshots of the level of understanding/ application. The ability to activate large groups (150−200 students) was considered an advantage. The amount of preparative work and time spent in class on the tasks are considered acceptable by the teachers, and they plan to use it more often in the future. From visual inspection during the tasks, it is the impression that a majority of students participate. One of us (M.W.) has explored all nodes depicted in the matrix (Figure 1). With respect to the open-ended questions, the answers can provide a rich insight into student thoughts when questions are selected strategically. Only a marginal amount of “silly” answers were posted. Indeed, open-ended questions can serve to conduct “expectation management” and/ or early “pitfall awareness” among the students. The 3D visualization tasks required considerable time investment due to the necessity to “test run” on multiple types of devices. Gratifyingly, though, these 3D tasks proved a very valuable addition to the lectures since concepts that do not always translate properly in 2D (molecular structures, interactions in a complex) could now be brought to more life by the teacher on the devices. Good instructions are key (see Figures S12 and S13 in the Supporting Information).

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CONCLUSION IT (information technology) is finding its way into contemporary education. We have demonstrated that this is for the better as it can provide a means to rapidly and simultaneously activate groups of students. Using appropriate apps/software and tasks, one can turn electronic devices (smartphones, tablets, laptops) into a powerful tool that can be used for formative assessment in the classroom. Larger groups of students, bold and shy ones alike, can be triggered to participate in small tasks such as answering MC and openended questions on class material. Moreover, the use of 3D visualization offers an in-class way to have students acquaint themselves with 3D structures of organic molecules, biomolecules, and drug−target complexes. These tasks should be thought of as being on one axis of a matrix, with the other axis being the application in any educational context (introquizzes, lectures, practical courses, etc.). Besides the positive experiences among teachers, we have found that students also appreciate and value these collective activating approaches. Taken together, we demonstrate that the use of mobile devices is a mutually beneficial way of teaching and therefore should deserve attention in other curricula, not only chemistry-based ones. Thus, while we have tailored all our electronic questioning to chemistry- and drug-related topics, it is evident that our protocols can be extended to nonchemistry classrooms too.

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Students

ASSOCIATED CONTENT

S Supporting Information *

Among involved courses, 6 (practical) courses have been subjected to electronic activating tasks at a notably intense level, and these were therefore concluded by a voluntary evaluation with students using the Likert scale and GoSoapBox (Tables S1−S7 in the Supporting Information). From the evaluation results, it has been gratifying to observe that students highly value our approaches. Certainly, occasional points for attention are given and these are taken along in further design. But in general the overall evaluations of in-class electronic tasks have been positive (Tables S1−S7 in the Supporting Information). Students appreciate the anonymous character, the “I do not know” option, the insights in class material and in 3D structures they obtain from the in-class tasks, etc. As a practical advantage, it is acknowledged by the students that the small interactive tasks help in keeping attention. The monthlong quiz in the synthesis practical course is highly valued for the anonymous character, for correlating theory and practice, for getting insights in the experiment, etc. The “game” aspect of

Features of key apps/programs, comparison of introquiz results of three consecutive academic years, effect of re-asking an introquiz question, exemplary question formats, and key evaluation results. This material is available via the Internet at http://pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS From the VU University Amsterdam, we wish to express thanks to Rob Leurs, Iwan de Esch, Chris de Graaf, Martine Smit, Henry Vischer, Marco Siderius, Chris Vos, Nico Vermeulen, F

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(18) Smith, M. K.; Wood, W. B.; Adams, W. K.; Wieman, C.; Knight, J. K.; Guild, N.; Su, T. T. Why Peer Discussion Improves Student Performance on In-Class Concept Questions. Science 2009, 323, 122− 124. (19) Holme, T. Using Interactive Anonymous Quizzes in Large General Chemistry Lecture Courses. J. Chem. Educ. 1998, 75, 574− 576. (20) The PubChem Project. http://pubchem.ncbi.nlm.nih.gov/ (Accessed Jan 2014). (21) RCSB Protein Data BankRCSB PDB. http://www.rcsb.org/ pdb/home/home.do (Accessed Jan 2014). (22) We have been experimenting with using .cif files from scientific articles as a rich source for visualizing crystallized molecules and host− guest complexes. However, the seemingly scarce availability of free and straightforward .cif viewing software for all device types was (as of Nov 2013) a large hurdle for this. (23) Berry, C.; Baker, M. D. Inside Protein Structures: Teaching in Three Dimensions. Biochem. Mol. Biol. Educ. 2010, 38, 425−429. (24) Winne, P.; Hadwin, A. The Weave of Motivation and SelfRegulated Learning. In Motivation and Self-Regulated Learning: Theory, Research, and Applications; Schunk, D. H., Zimmerman, B. J., Eds.; Lawrence Erlbaum Associates: New York, 2008; pp 297−314. (25) Biggs, J. Teaching for Quality Learning at University, 2nd ed.; Open University Press: Buckingham, 2002. (26) Federspiel, M.; Fischer, R.; Hennig, M.; Mair, H.-J. r.; Oberhauser, T.; Rimmler, G.; Albiez, T.; Bruhin, J.; Estermann, H.; Gandert, C.; Gockel, V.; Gotzo, S.; Hoffmann, U.; Huber, G.; Janatsch, G.; Lauper, S.; Rockel-Stabler, O.; Trussard, R.; Zwahlen, A. G. Industrial Synthesis of the Key Precursor in the Synthesis of the AntiInfluenza Drug Oseltamivir Phosphate (Ro 64-0796/002, GS-410402): Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene1-carboxylate. Org. Process Res. Dev. 1999, 3, 266−274. (27) Wijtmans, M.; Scholten, D. J.; Roumen, L.; Canals, M.; Custers, H.; Glas, M.; Vreeker, M. C.; de Kanter, F. J.; de Graaf, C.; Smit, M. J.; de Esch, I. J.; Leurs, R. Chemical Subtleties in Small-Molecule Modulation of Peptide Receptor Function: The Case of CXCR3 Biaryl-Type Ligands. J. Med. Chem. 2012, 55, 10572−10583. (28) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families. J. Am. Chem. Soc. 2005, 127, 12984−12989. (29) Coste, F.; Malinge, J. M.; Serre, L.; Shepard, W.; Roth, M.; Leng, M.; Zelwer, C. Crystal Structure of a Double-Stranded DNA Containing a Cisplatin Interstrand Cross-Link at 1.63 Å Resolution: Hydration at the Platinated Site. Nucleic Acids Res. 1999, 27, 1837− 1846. (30) Crescenzi, O.; Tomaselli, S.; Guerrini, R.; Salvadori, S.; D’Ursi, A. M.; Temussi, P. A.; Picone, D. Solution Structure of the Alzheimer Amyloid Beta-peptide (1−42) in an Apolar Microenvironment. Similarity with a Virus Fusion Domain. Eur. J. Biochem. 2002, 269, 5642−5648. (31) Ogbay, B.; Dekoster, G. T.; Cistola, D. P. The NMR Structure of a Stable and Compact All-Beta-Sheet Variant of Intestinal Fatty Acid-Binding Protein. Protein Sci. 2004, 13, 1227−1237. (32) Rasmussen, S. G.; Choi, H. J.; Fung, J. J.; Pardon, E.; Casarosa, P.; Chae, P. S.; Devree, B. T.; Rosenbaum, D. M.; Thian, F. S.; Kobilka, T. S.; Schnapp, A.; Konetzki, I.; Sunahara, R. K.; Gellman, S. H.; Pautsch, A.; Steyaert, J.; Weis, W. I.; Kobilka, B. K. Structure of a Nanobody-Stabilized Active State of the Beta(2) Adrenoceptor. Nature 2011, 469, 175−180. (33) Hardegger, L. A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher, J. M.; Hartmann, G.; Isshiki, Y.; Morikami, K.; Shimma, N.; Haap, W.; Banner, D. W.; Diederich, F. Halogen Bonding at the Active Sites of Human Cathepsin L and MEK1 Kinase: Efficient Interactions in Different Environments. ChemMedChem 2011, 6, 2048−2054.

Romano Orru, Hubertus Irth, Johan Vermeer, and all other fellow teachers as well as Danny Scholten, Jelle Reinen, Albert Kooistra, and all other PhD students/postdocs involved in our teaching activities. Willem-Jan van Zeist, Bart van Ommen, Rob van Leeuwen, and Michel Jansen (all from VU University) are acknowledged for logistical and/or technical assistance. Benjamin Berte (Socrative), Dave Mulder and John Pytel (GoSoapBox), and Andrew Orry and Eugene Raush (MolSoft) have been instrumental in technical communications, for which we are grateful. All involved Bachelor and Master students are acknowledged as the exploration of electronic tasks would not have been possible without them. We thank Tabitha Sprau Coulter (Pennsylvania State University) for proofreading the manuscript. M.W. is grateful to the Royal Netherlands Chemical Society (KNCV) for awarding its annual national teaching prize to him, based substantially on work described in the current manuscript.

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REFERENCES

(1) Sawyer, R. K. Cambridge Handbook Of The Learning Sciences, 1st ed.; Cambridge Press: New York, 2006. (2) Freeman, S.; Eddy, S. L.; McDonough, M.; Smith, M. K.; Okoroafor, N.; Jordt, H.; Wenderoth, M. P. Active Learning Increases Student Performance in Science, Engineering, and Mathematics. Proc. Natl. Acad. Sci. U.S.A. 2014, DOI: 10.1073/pnas.1319030111. (3) Goldberg, F.; Price, E.; Robinson, S.; Boyd-Harlow, D.; McKean, M. Developing the Learning Physical Science Curriculum: Adapting a Small Enrollment, Laboratory and Discussion Based Physical Science Course for Large Enrollments. Phys. Rev. Spec. Top.Phys. Educ. Res. 2012, 8, 010121-1−010121-24. (4) Williams, A. J.; Pence, H. E. Smart Phones, a Powerful Tool in the Chemistry Classroom. J. Chem. Educ. 2011, 88, 683−686. (5) Njardarson, J. T. Reactions at Your Fingertips. Nat. Chem. 2012, 4, 590. (6) Libman, D.; Huang, L. Chemistry on the Go: Review of Chemistry Apps on Smartphones. J. Chem. Educ. 2013, 90, 320−325. (7) Williams, A. J.; Ekins, S.; Clark, A. M.; Jack, J. J.; Apodaca, R. L. Mobile Apps for Chemistry in the World of Drug Discovery. Drug Discovery Today 2011, 16, 928−939. (8) Carroll, J.; Rodgers, J.; Sankupellay, M.; Newcomb, M.; Cook, R. Systematic Evaluation of GoSoapBox in Tertiary Education: A Student Response System for Improving Learning Experiences and Outcomes. In 8th International Technology, Education and Development Conference, 10−12 March 2014, Valencia, Spain. (9) Yiu, C. P.; Chen, Y. W. High-Quality Macromolecular Graphics on Mobile Devices: A Quick Starter’s Guide. Methods Mol. Biol. 2014, 1091, 343−352. (10) Hanson, R. M. JmolA Paradigm Shift In Crystallographic Visualization. J. Appl. Crystallogr. 2010, 43, 1250−1260. (11) Shaver, M. P. Using Low-Tech Interactions in the Chemistry Classroom To Engage Students in Active Learning. J. Chem. Educ. 2010, 87, 1320−1323. (12) Mazur, E. Peer Instruction: A User’s Manual, 1st ed.; Prentice Hall: Upper Saddle River, 1997. (13) Mazur, E. Education. Farewell, lecture? Science 2009, 323, 50− 51. (14) Bae, J.-H.; Kim, S.-K. Research on Educational Use of SmartPhone Applications with Smart Clicker Technique. Lect. Notes Electr. En. 2014, 279, 597−602. (15) Socrative | Student Response System. http://www.socrative. com/ (Accessed Jan 2014). (16) Student Response SystemLearn from Your Students GoSoapBox. http://www.gosoapbox.com/ (Accessed Jan 2014). (17) Wagner, B. D. A Variation on the Use of Interactive Anonymous Quizzes in the Chemistry Classroom. J. Chem. Educ. 2009, 86, 1300− 1303. G

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(34) Qiu, H.; Dewan, J. C.; Seeman, N. C. A DNA Decamer with a Sticky End: The Crystal Structure of d-CGACGATCGT. J. Mol. Biol. 1997, 267, 881−898. (35) Dempster, F. N. Synthesis of Research on Reviews and Tests. Educ. Leadership 1991, 48, 71−76.

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