ChemVoyage: A Web-Based, Simulated Learning Environment with

Article pubs.acs.org/jchemeduc

ChemVoyage: A Web-Based, Simulated Learning Environment with Scaffolding and Linking Visualization to Conceptualization Christopher McRae, Peter Karuso, and Fei Liu* Department of Chemistry & Biomolecular Sciences, Macquarie University, NSW 2109, Sydney, Australia S Supporting Information *

ABSTRACT: The Web is now a standard tool for information access and dissemination in higher education. The prospect of Web-based, simulated learning platforms and technologies, however, remains underexplored. We have developed a Webbased tutorial program (ChemVoyage) for a third-year organic chemistry class on the topic of pericyclic reactions to illustrate this approach with scaffolding and visual auxiliaries. The questions in the tutorial are tiered to simulate the pyramidal structure of knowledge and interlinked to form concept maps required to aid student learning. Visual cues and remedial exercises are linked to advanced questions to facilitate integration of knowledge. Students advance through lower levels to reach higher levels at their own pace. This Web-based learning program provides flexible delivery for the learner and records the learning history of an individual user for the instructor. The diagnostic information helps with reflective teaching and facilitates independence of the learner. Student feedback shows that this is an effective approach in improving their learning outcomes. KEYWORDS: Upper-Division Undergraduate, Organic Chemistry, Computer-Based Learning, Internet/Web-Based Learning, Problem Solving/Decision Making, Reactions, Stereochemistry, Student-Centered Learning

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he wide availability of the Internet and mobile devices has clear advantages in delivery of information and content independent of time and place.1 However, students still face the same learning barriers typically associated with the comprehension of abstract concepts.2 This imposes some challenges in designing effective Web tutorials for the physical sciences where concepts are sometimes too abstract to grasp by simply accessing more information. Conventional Web-based tutorial programs are effective in testing student comprehension and assisting in content delivery.3 However, from our student feedback, it appears that many students feel that conventional programs can be deficient in scaffolding and consideration of different levels of a student’s prior knowledge. Part of this need can be addressed through design of the interface,4 but the more effective approach may be to use Web-based tutorial programs to also facilitate cognitive maturation and induce constructive learning, in addition to just information and content delivery. Preferably, a Web-based tutorial interface should allow the student to explore a concept map in a multidimensional manner with gradual scaffolding and flexibility to achieve depth in understanding. With the understanding that technology is useful in facilitating student development, a scaffolding program with visual cues and animations to assist in this development was sought.5 Here we describe the design and creation of such a simulated learning environment (SLE) for a third-year organic chemistry topic as a model system. © 2012 American Chemical Society and Division of Chemical Education, Inc.

DESIGN OF A SCAFFOLDED WEB TUTORIAL WITH VISUAL CUES The goal of the Web-based tutorial program (ChemVoyage) was to facilitate the understanding of difficult, abstract concepts frequently encountered in upper-level chemistry. Pericyclic reactions from a third-year organic chemistry course were chosen as they are considered one of the most challenging sections of organic chemistry by the students. The following discusses first the theory behind a scaffolded learning approach, then the structural blueprint of the tutorial within this scaffolding theory, and finally some logistical criteria for enabling this simulated learning environment online. Theoretical Framework of Learning

The general framework of learning stages follows the model by Säljö,6a who is acknowledged as the pioneer in research into students’ conceptions of learning that fostered decades of subsequent refinement of his model under varying names and attributes. From these models, five qualitatively different levels can be described as (a) increase of knowledge, (b) memorizing, (c) acquisitions of facts or procedures that can be retained or utilized in practice, (d) abstraction of meaning, and (e) an interpretative process aimed at the understanding of reality. The last two stages roughly correspond to the “deep” approach to learning defined by Entwistle, whereas the first three stages could be defined as “surface” approaches.6b Also noted is that a “deep” approach (or abstraction and synthesis) may not be the Published: April 19, 2012 878

dx.doi.org/10.1021/ed200533u | J. Chem. Educ. 2012, 89, 878−883

Journal of Chemical Education

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Figure 1. A Web-based program with three levels for staged learning. The user starts with tasks of information retrieval in level 1 and advances to tasks of problem solving in level 3 that require correct mapping of related concepts.

fifth stage). This approach is represented in Figure 1, where the learning tasks are divided into three levels. At level 1, 30 questions address the need to learn key terms, definitions, and basic concepts (to know what is). At level 2, 10 questions are presented with visual cues. The learner is asked to choose the correct explanation for a given observation or question with the option of referring to relevant information from questions in level 1. Feedback is given after correct or incorrect attempts. At this level, connections are made between basic units of terms, definitions, and concepts to explain given observations. At level 3, 10 questions are also presented with visual cues. The learner is asked to choose the correct solutions to complex problems, again with the option of referring back to relevant questions from level 1 and level 2 and feedback after correct or incorrect attempts. At this level, the learner witnesses how the correct sequential application of level 2 connections leads to problem solving.

most appropriate approach in every situation. Laurillard, while trying to correlate the ideas of Marton, Pask, and Svenssen, concluded that in the sciences, students cannot see an overview or inter-relation of ideas (deep or holist) until knowledge has reached some critical mass.6c She argues eloquently that this does not mean the mere accretion of facts but the building of a language of precisely defined terms (shared knowledge) and evidence. Thus, memorization (surface) and concentration on details (atomist) and logical relationships (serialist) may be prerequisites to understanding with the use of metacognitive skills (knowing when it is appropriate to use different learning techniques).7 Structural Blueprint of a Scaffolded Tutorial Interface with Visual Cue

Given the theoretical framework above, the difficulty with learning in physical sciences is primarily associated with arriving at the last two stages, in which construction of the correct sequential “tree” of multiple learning outcomes is required for problem solving. The approach to a good tutorial therefore needs to take on a constructivist view of these learning stages and apply “concept maps”, where concepts are presented in an integrated manner (from information gathering at the start to synthesis of knowledge for problem solving at the end).8 At the more advanced levels, the importance of a student’s prior knowledge becomes paramount.9 The integration of prior knowledge with new learning into concept maps has been proposed to engender meaningful learning in chemistry.10 The learning program therefore needs multiple levels to scaffold the process of understanding (from information accumulation to enhanced conceptualization) before applying that understanding to problem solving. This scaffolding, in reflection of the stages of learning, should encourage engagement and learning independence.11 In additional to scaffolding, abstract concepts in physical science benefit from visualization cues.12 These visual aids help students eradicate misunderstanding of key concepts.8,9 Thus, the lowest level of the program should start with the simplest terms and definitions. As the level of difficulty increases from accumulation of knowledge, visual cues are introduced as concepts become more complex and abstract. When students ultimately arrive at the level of understanding that is sufficient for problem solving, a history of how they arrived there is presented, along with all the necessary concepts and definitions involved. This can generate a concept map to help make connections and move the student from abstraction of meaning to an integrated understanding of reality (Säljö’s

Logistical Criteria for Effective Learning Support

With the theoretical framework of learning and a corresponding structural blueprint of the learning program in hand, the next issue became the practical tactics that would make this simulated learning environment effective. Ideally, it should simulate an academic or instructor in class or tutorial sessions to help students achieve cognitive growth but with a higher capacity at recording learning profiles for diagnosis.13 The program therefore needs to include the following capabilities: flexible use and access, diagnostic value, and a constructive learning atmosphere. Flexible Use and Access. Flexibility is a prerequisite to engaging students in the information age as students expect content to be available at any time from anywhere. It is also known that a safe learning environment is important for effective learning.10d Thus, a learning platform could resemble a Web-based game that contains an “orientation activity” to initially tune in the student and an engaging mechanism without bias. The program should have no time limit and few language barriers through visual cues. It should work for students of all levels and backgrounds to maximize equity in learning opportunities. Diagnostic Value. The tutorial can monitor a learner’s interaction with the program and serve as an objective and faithful observer of the learner’s own progress. Parameters reflecting the learning curve (e.g., times taken to answer questions, number of attempts, etc.) should be recorded. This will allow the instructor and learner to identify difficulties going 879



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Figure 2. An example question (Q1) from level 2: (A) The Q1 question button turns brown after the first incorrect attempt. The “use a lifeline” and “show me the answer” buttons appear. (B) In the “lifeline” mode of Q1 of level 2, four related questions from level 1 are ready for reviewing. The green colors of the level 1 question buttons indicate that the user had previously attempted these questions correctly. (C) In the “show me the answer” mode, an explanatory note is given.

and 2; Level 2, explanation and elaboration, Säljö stage 3; Level 3, solve new problems, Säljö stage 4 and 5). Each question has one correct answer and three incorrect answers. The incorrect answers come from past exams and tutorials to reflect common misconception and misunderstanding students have exhibited. Reaching the correct answer on first attempt incurs the maximum positive points with a feedback note to confirm the thinking behind the correct answer. Each wrong attempt incurs negative points and prompts remedial directions from the program (see below). This is to discourage the nonproductive behavior of random clicking just to see the correct answer. For questions at level 1, students are asked to refer to the textbook for feedback or finding the right answer. For questions in level 2 and 3, feedback is given in two modes when the first attempt fails to find the correct answer (Figure 2A). Users can choose the feedback mode that entails a remedial exercise (“use a lifeline”, Figure 2B) or the direct feedback mode (“show me the answer”, Figure 2C). By clicking “use a lifeline”, the user enters a temporary time-out screen to review lower level(s) of questions and their feedback notes that are relevant to the question being attempted. This is analogous to a gaming scenario where the “player” goes to a special place to recharge power or gain additional weaponry for more difficult tasks. With further review and studying, the user can attempt the question again with strengthened understanding upon exiting the lifeline mode. The use of a lifeline mode also brings the user compensation points. Thus, good learning behavior is positively rewarded (see the Supporting Information). In the direct

from a reproductive mode in the early questions to a constructivist mode in the later questions. The instructor can then address learning difficulties in a timely fashion.11 Diagnostic information from this program may support collaborative teaching and learning. Constructive Learning Atmosphere. From the student’s perspective, clear and immediate feedback is always welcome in any tutorial. The amount of feedback offered can be correlated to the perceived level of difficulty with the user option of choosing how much feedback is needed. In addition, the student can use an avatar for the tutorial to navigate through the program like a game with perhaps less anxiety. The program should meet all these requirements without imposing judgment on pre-existing levels of knowledge on any student other than the prerequisites required to get into the course. Every student can navigate through the levels according to the individual’s own pace, timetable, and start level. It should be emphasized that, whereas it is accepted that a variety of preexisting conditions affect how a particular student would learn in a particular class, these prior conditions cannot be changed but only managed or ameliorated by adaptive learning approaches that are cognizant of these constraints.

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RESULTS

Implementation of the Web Tutorial

The tutorial currently contains three levels aligned with Säljö learning stages (Level 1, basic facts and definitions, Säljö stage 1 880



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Figure 3. An example question (Q4) from level 2 with visual cues: (A) An option of visualization (“play a movie”) and (B) a movie (in Jmol) allows for step-by-step visualization.

feedback mode (Figure 2C), the “show me the answer” note for having chosen an incorrect answer is explanatory, where more details are given to show how mistakes can arise. Once the “show me the answer” option is used, the question cannot be attempted again and no positive points can be scored. This option is provided to address the scenario that there may be students who would still be unable to problem solve after all other remedial options have been exhausted. A student must complete all questions correctly in a level before moving onto the next. The completion of a question is not judged as having clicked on an answer out of four for a given question. A student is allowed three attempts to find the correct answer of a question. Therefore, the tutorial is not just for self-testing but used as an opportunity to self-navigate one’s own thought process and diagnose potential deficiencies. The color of a question button changes to indicate how many attempts have been used up. A student therefore has the option to conduct the first attempt on a particular question, move onto a different question, and then return to the initial question at a later time. With the correct answer chosen or exhaustion of three attempts (which ever comes first), the color of a question button will be changed to gray to indicate that this question is complete and now in viewing mode only. Thus within the same level, the user has complete flexibility in deciding how and in what order the questions can be tackled. For questions, particularly at level 2 and level 3, that require spatial recognition of a particular molecule or transition state, the user can mouse over a 2D drawing to click on a 3D viewing button to see a Jmol14 representation that is rotatable and available in stereoview (Figure 3A). Some questions that involve visualizing molecular motion also offer movie-viewing modes to illustrate the molecular interaction and how that leads to a particular stereochemical outcome (Figure 3B). The movies are generated by using multiple PDB files derived from high level DFT (density functional theory) calculations (see the Supporting Information).15 The user can enter the program by using an avatar, much like in a Web-based interactive game (IT interface details are found in the Supporting Information). The availability of an avatar brings some amusement to an otherwise fairly strenuous learning experience. All avatars and their scores are known to all users of the program to create a virtual sense of competition. The sense of anonymity in a virtual world via an avatar may protect against discouragement in learning. It has been shown that combining an inquiry-based learning model with the use of

avatar-based virtual environments can be motivating and educationally valuable for students.16 A report card (see the Supporting Information) showing the scores of all avatars is available for self-assessment at any time. For the instructor, detailed usage information of each user’s track record on every question (e.g., how many wrong attempts, how many lifeline uses, how many “show me the answer” uses, etc.) was examined. Tracking student usage has previously been advocated to dynamically adapt aspects of the contents and improve learning outcomes.17 Good instruction requires educators to be aware of the learning progress of students and dynamically tailor lectures according to students’ preparation and mastery of the course material. This has led to the development of applications such as Moodog to track student usage of Moodle course material.18 Student Feedback on the Web Tutorial

As a voluntary, self-learning Web-tutorial (not an assessment), the ChemVoyage program was released to the students in a third-year organic chemistry course (no distance education students) after all lectures and in-class tutorial sessions have been completed on the topic. A dozen students trialed the program. Nine of these users completed the program, eight of which returned their post-use survey (see the Supporting Information). When asked the key question if this kind of tutorials would be helpful for other upper-level topics (with 1 = not helpful to 10 = very helpful), the average score was 9.25/ 10. One interesting student comment states: ...Otherwise [this] is an extremely awesome idea, and I was very impressed with the program as a whole. It also revealed some of my latent anger which is probably a good thing. Although the program was not intended to reveal the psychological color of any particular user, this “inadvertent” admission at least supports the idea that the program is more than just an information portal but can allow the users to reflect on their learning and get more feedback than just scores. The visual cues were considered helpful, although an interesting question was raised about what to do (e.g., in an exam) if the visual cue would not be there. This revisits perhaps a longstanding paradox in learning and teaching: If too much effort is made to help students learn more easily, does that reduce their chance to gain more learning resilience (i.e., no pain no gain)? The comments also pointed to some interesting student views that were not anticipated. For example, some students felt that the lifeline option was not flexible enough as it did not allow 881



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Currently, this Web program is sculpted to allow individual navigation in a predetermined format. In reality, some students prefer to learn in groups, and learning outcomes do not have to be set in stone when using online modes.19 Apart from the basic human need of a social environment, the pedagogical advantages of peer-assisted learning come from rapid and diverse feedback that enhances the learning process.20 Therefore, more advanced platforms of this tutorial must include capabilities of interactive modes in which students can choose to navigate in groups of various sizes.21 There ought to also be options where students in a group can decide collectively on new levels of challenge on which to embark, apart from the level set by an instructor. To go even further, certain editing privileges can be given to student users on merit, who would be asked to create new challenging tutorial questions. In short, social modes of learning need to be enabled in this learning environment so it can evolve to facilitate new challenges that students can set for themselves.

the reviewing of all lower-level questions but only those related to the current question and it did not allow a retackle of a question after it has been completed. This preference, while implementable in a second-generation program, also suggested that some students still viewed learning activities as goals and focused on completion of the apparent learning activities, even though these activities were intended to be only clues to help them identify deficiencies and learn productively (learn how to learn). Some common sense wisdom is reinforced againwhat is viewed as necessary or important by the students can be quite different from that intended by the instructor, and any mechanism that could bridge this gap would likely help with the learning outcomes. The use of this program overall was found to be educationally effective by the students, and the instructors also became more knowledgeable about the learning profiles of students. To improve further on this program given the student feedback, more personalized feedback mechanisms need to be incorporated. For example, some students wished to review all lower-level questions or even reattempt them. More flexible review modes of questions can be implemented accordingly. Another possibility is to provide a third mode of remedial exercise in the lifeline mode, where a student could be asked a set of diagnostic questions related to the problem at hand to identify more directly learning deficiencies. The focus for the next generation program will be the customizability of this type of simulation. Although the scale of this proof-of-concept study was small, its monitoring capacity nonetheless provided useful information as to what learning tasks were considered difficult by the users (not just by the instructor). For example, the number of times questions in the “lifeline” mode were accessed was recorded. This number doubled going from level 2 to level 3, which is consistent with the fact that level 3 questions are more difficult as they required synthesis of knowledge for problem solving. Different users recorded different navigational profiles, although some problems, particularly the ones involving more elaborate stereochemical solutions, were more consistently identified as demanding and correspondingly were revisited in the review lectures. This also suggests that the lecture and workshop component of the course can be focused more on this particular aspect of the topic in the future.

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ASSOCIATED CONTENT

S Supporting Information *

User instructions; IT Interface strategy; sample codes for generating movies suitable for display in Jmol in .pdb format; and user feedback. This material is available via the Internet at http://pubs.acs.org. Access to ChemVoyage can be obtained by emailing the corresponding author.

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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 The authors thank the Learning and Teaching Center of Macquarie University for their technical assistance. This work was funded by a Priority Learning and Teaching grant from Macquarie University to F.L., C.M., and P.K. and an Emerging Technology grant from Macquarie University to C.M. and F.L.

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CONCLUSION AND NEW CHALLENGES In summary, a staged, self-navigational, visually enhanced, and game-like Web tutorial was implemented as a simulated learning environment for a third-year organic topic and has now become part of the course tutorial content. Apart from physically seeing visual cues that directly assist learning, students also “witness” their own learning progress. The logic behind this program makes it extendable, in its educational structure, to other physical sciences. By simply changing the modular visual links (graphic files and text files), this platform can be readily adapted and expanded laterally to include other topics of chemistry. Vertically, further layers can be constructed, more sophisticated feedback loops can be incorporated, or existing layers can be broken down to smaller steps on the basis of student demand. In terms of learning feedback improvement, questions can be tagged with concepts associated for a better plot of the user’s cognitive progress. The adaptable nature of this platform may lead to more general applications that empower students to engage in difficult learning tasks with more independence.

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ChemVoyage: A Web-Based, Simulated Learning Environment with

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