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Sep 6, 2017 - that make up a final report. KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Laboratory Instruction, Organic Chem...
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A Project Provides an Opportunity: Multiple Drafts of an Introduction Require Students To Engage Deeply with the Literature David J. Slade* and Justin S. Miller Department of Chemistry, Hobart and William Smith Colleges, Geneva, New York 14456, United States S Supporting Information *

ABSTRACT: A 10 week project in the organic chemistry laboratory provided the opportunity to require students to write four drafts of an introduction. Student understanding of what a good introduction entails was transformed by their fourth draft, as evidenced by higher citation counts and the inclusion of more and better figures, which reveals greater student engagement with the primary literature. In the initial implementation of the project, writing subsections of the final report throughout the semester had the unfortunate effect of creating loosely related but standalone assignments for students. Replacement of the subsection work with four drafts of the introduction section required students to re-examine their own work, respond to feedback, and investigate the primary literature in greater depth. Faculty grading time is now focused on requiring students to understand the background literature of the project deeply and to write a compelling introduction, as opposed to asking students to briefly engage the other subsections that make up a final report. KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Laboratory Instruction, Organic Chemistry, Communication/Writing, Learning Theories, Professional Development

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CONTEXT: IMPLEMENTATION OF A PROJECT

A standard end goal of many projects is the writing of a journal-like article, with members of the BYUIdaho chemistry department going so far as to create an in-house journal, The Journal of Kitchen Chemistry, from students’ projects.16 For the first iteration of the HDACi project, the goal of the students would be to write a mock Organic Letters article to be submitted on the last day. While the final assignment was an obvious choice, literature surrounding writing across the curriculum has made clear that students should write as many smaller assignments as is feasible.17,18 These smaller writing samples provide “writing to learn”19−21 opportunities, so mini-assignments were assigned on a weekly basis throughout the semester. Students were asked to write a group report for the final summary of the project, primarily because authentic journal articles are so frequently written collaboratively. However, a significant individual component to the writing was also deemed necessary in order to provide proper incentives for all students to contribute meaningfully. The most obvious approach was to build a final group report by asking each individual student to write each desired subsection once.22−25 The sequence of mini-assignments for the first implementation was the following: introduction, results, discussion, experimental, future directions, and abstract. Each individual

In 2012, the Organic Chemistry II laboratory was completely revamped by replacing a host of traditional and unrelated experiments with a 10-week-long project-based experience.1 The histone deacetylase inhibitor (HDACi) project was funded by an NSF-TUES grant, with the primary goals being (1) to investigate if including a research project into the laboratory increased student engagement in either lecture, laboratory, or both; and (2) to link Organic Chemistry II more closely with a cell biology course. The compounds synthesized by students in the chemistry course would then be tested for apoptotic potential in a future semester, possibly by the very students who had synthesized them. As a direct consequence of these goals, attention during the first implementation was focused on (1) translating a research project into a form suitable for a course, (2) linking the lecture and laboratory more closely together, and (3) discovering what a realistic end point for a 10week-long synthetic effort would be. Many have likewise converted traditional coursework into a project format: there are >3400 hits for the search terms “project based learning” in this Journal alone.2 These hits span a wide range of coursework, with references selected to illustrate some of that breadth.3−13 Reviews of the adoption of projects in organic chemistry14 and biology15 laboratories have concluded that students have more positive attitudes toward research and an increased interest in pursuing research in project-based laboratories versus more traditional options. © XXXX American Chemical Society and Division of Chemical Education, Inc.

Received: February 17, 2017 Revised: August 13, 2017

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and its analogues (the chemical background). The importance of the introduction subsection, especially given the amount of difficult reading in the literature that was necessary, demanded a significantly higher point value than the other subsections. By making the introduction the focus of student attention and faculty grading time, students would be required to engage the primary literature. Due to the nature of a solid-phase synthesis, very few results were available for discussion by students in their final papers. On-resin analysis was minimal, and though the identity of the final compound was confirmed by NMR spectroscopy, the task of describing the NMR results was ill-suited to the introductory organic chemistry setting. With few results to discuss, and no significant structural analysis component, the results and discussion sections were dramatically de-emphasized by both combining them and reducing their point value in the next iteration of the final report. Finally, though good figures are crucial in organic chemistry articles, the prompts for the assignments had failed both to adequately inform students of the importance of visual aids and to prepare students to generate effective figures. It was clear that the entire sequence of assignments needed to be reshaped, placing more value on the elements that matter the most to faculty, signaling to students the relative importance of each element, and aligning grading policies and assignments with the desired final product (Table 1).

student’s submission was graded by faculty, with the hope that feedback provided to individuals would eventually be incorporated into the final (group) report. Because commentary had been provided, and students wrote a final project together, it appeared to faculty as though students had been asked to write a second draft of all assignments. This initial implementation necessarily involved developing the week-to-week laboratory protocols required for student success at the bench. Upon completion of the semester, with the benefit of hindsight, we realized that a multiweek project provides an opening to require multiple drafts of assignments. The sequence of assignments initially selected provided a chance for the weakest students to coast on the work of their stronger colleagues, and an opportunity had been missed to require the weakest students to revise their own work.

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AN OPPORTUNITY MISSED An extremely valuable component of a research project-like experience is the ability to build constructively upon student work rather than simply to require the next assignment to be handed in. Unfortunately, breaking the final paper into its components had the unintended effect of requiring students to write a series of one-off assignments. Students struggle25,26 to write these segments of journal articles because they are not yet skilled readers27 of the chemistry literature. Each student submission of an introduction, abstract, or any other subsection is essentially the student’s first attempt at writing in this style.28 Even if students have previously written a journal article in another chemistry course, which is unlikely at the introductory level, they are almost certainly unfamiliar with the demands that each chemical subdiscipline imposes.29 In other words, though these mini-assignments are crucial components of a single coherent article, these connections are not apparent to secondyear undergraduate students. Both individual and group assignments had been selected in order to encourage collaborative work while discouraging social loafing. Unfortunately, the sequence of assignments did not require students to engage with faculty feedback. In principle, faculty commentary on each individual’s writing could eventually inform the group report, which students were instructed to write as though a single intelligence had crafted it. Instead, of course, students assembled a Frankenstein’s monster from the best individual subsections before attempting to edit the whole for style and content. Only the best first attempt at each subsection from among the group was relevant, and the other students were free to ignore faculty feedback. Worse, since the plan for the semester was explicitly laid out, students were able to rely on the output from the strongest of their peers when assembling their final group reports. Ideally, all students would have been required to be active participants in improving their own work through engaging with faculty commentary26 and writing repeated drafts,30−35 but instead the mix of short assignments allowed them to read the comments passively, without needing to take corrective action. Another error in the initial implementation was assigning equivalent point values to all subsections of the final paper. The nature of the project (a solid-phase synthesis of analogues of the anticancer drug Romidepsin36 based on the reported solution-phase1 approach) ensured that the introduction was the most important subsection of their eventual paper. Students were instructed to explore the primary literature, especially regarding the mechanism of action of HDAC inhibitors (the biological background) and previous syntheses of Romidepsin

Table 1. Replacing One-Off Assignments with a Drafting System Week of Project

Initial (2012) One-Off Approacha

3 4 5 6 7 8 9 10

Introduction Results Discussion Experimental (group) Future Directions Abstract

Last day of classes

Final full paper (group)

Drafting (2013−Present) approachb 1st introduction Figure and schemec 2nd introduction Experimental (group) 3rd introduction 1st abstract 4th introduction 2nd abstract and 1st full paper (group) 2nd full (group)

a

A single draft was submitted for all assignments. Submissions were individual except where noted. bSpecifics described in the Supporting Information. cOne example each of a figure and a scheme with some supporting text, graded largely on the basis of correct structures and correct formatting.

For the second implementation of the project, advantage was taken of the opening that the project provided in order to ask students to improve their writing through a series of drafts.30−35,37 Repeated, individual drafts provided students with a simulated experience of being professional writers, while improving their final results. Students were required to grapple with feedback, revisit their own work, and attain the understanding of the project that they needed in order to write effectively. The extended timeline of a project-based laboratory experience provides a golden opportunity to require students to engage in thoughtful re-evaluation37 of their work, and the assigned work should be designed to exploit the opportunity. B

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DRAFTING IN A PROJECT-BASED LAB

recommend this approach of phasing in a new long-term drafting system in order to establish a reasonable final target for future students. The primary goal when developing the drafting system for the introduction was to require students to read, understand, and reference more of the primary literature. Even the “two paragraph” 2012 prompt was quite clear that students should be referencing the literature, but expecting deep engagement with the literature in a student’s first draft is unrealistic, largely because of the significant amounts of time required to read and understand journal articles. The inherent difficulty of the task is further compounded by the tendency of students to procrastinate, or, perhaps, to underestimate the time required to read the literature. In addition, students had only recently encountered some necessary background in the lecture portion of the course. Multiple drafts extend the total time that students can profitably engage the literature to several weeks. Students can discover that reading and understanding the literature takes more time than they expected as they are writing their first drafts, when they still have time to correct their approach. When the first drafts are returned, students learn that using the primary literature is a requirement, and not optional. Starting in 2013, students had 3 more drafts and 6 more weeks to read more literature and improve their work, as well as the incentive to do so. Even the most stubborn of procrastinators were eventually convinced by the second or third draft to include more references (Figure 1).

Updated Approach

The 10 week timeline suggested four drafts of the introduction in order to (1) provide a bit of flexibility for the remaining assignments, and (2) provide 2 weeks for students to engage the primary literature before submitting the first draft. The abstract was retained as an individual assignment because it served as a summary of the entire project while being short and minimally time-consuming to write and grade. A second draft was added to the abstract, in part because of the difficulty of preparing a good graphical abstract for the project, and also to reinforce the need for multiple drafts when writing. As students are generally reluctant to include key results in the first draft of their abstracts, a second draft allows them to adjust accordingly. An assignment dedicated to the preparation of good figures and schemes was devised in order to signal explicitly to students the importance of visual aids, and to teach students how to generate good ones. Though only a single draft of the assignment was collected, points dedicated to visual aids were explicitly folded into the rubrics for all subsections and the final paper (rubrics are in the Supporting Information). Naturally, the quality of visual aids is quite important in other subsections, so effectively all assignments after the first draft of the introduction contained additional drafts of the figures and schemes. Reinforcing the global point that “the secret to good writing is rewriting”,30 a rough (group) draft of the final full paper was added. The group rough draft contained students’ first attempts at a results and discussion section, a future directions section, and a conclusions section. The rough full paper also required students to revise the group experimental section that had been previously submitted, so that the final draft of the full paper would contain their third attempt at writing an experiment section in the style of a Supporting Information document. As their group rough full paper was submitted simultaneously with the due date of the second abstract, the group authorship process (including writing of a group abstract) provided them, in effect, with an informal peer-review exercise of their own abstract. The due dates were chosen in part to minimize the “Frankenstein’s monster” behavior, but it is a rare group of students that does not attempt to simply plug in the best subsections from their group, possibly with some token updates.

Figure 1. Analysis of variance showed that that the effect of requiring multiple drafts of students’ introductions on total references employed was significant, F(4, 280) = 124.1, p ≪ 0.01. Post hoc analyses (Tukey−Kramer) revealed all pairwise comparisons were statistically different except for 2012 (purple) and the first drafts in 2014−16 (red). *In 2013 students were allowed to opt out whenever they pleased, with 32/43 completing all four drafts. The 2013 data were extracted from the last draft submitted for all 43 students.

Did a Focus on the Introduction Work?

The drafting approach caused students to dramatically transform the shape and content of the introduction sections, compared to the 2012 baseline cohort. The misguided 2012 prompt asked for a “two paragraph” introduction with the explicit intent of making the assignment equal in point value and importance to the other subsections. In the 2013 prompt, students were informed that the introduction was worth twice as many points as the other mini-assignments and that they could write up to four drafts of it. As it was unclear how good a student introduction could become by the fourth draft written, for 2013 an “opt out” system was put into place. Students were asked to submit four drafts of the introduction, but could elect to stop submitting drafts when they were satisfied with their score. Only 11 of the 43 students in the 2013 cohort elected to stop after the second or third draft, with 32/43 submitting the full complement of four drafts. Once the final introductions for each student in the 2013 cohort had been graded, a realistic quality goal could be established for the 2014−16 cohorts. We

The writing prompts have remained largely unchanged since 2013, but starting in 2014 more written support and more guidance in prelab lectures was offered, as a realistic expectation for the quality of the final draft of the introduction had been established. In addition, questions were added to the problem sets in the lecture portion of the course that were designed to (1) introduce key concepts from the lab into the lecture, and (2) ease students’ transition into reading a particularly important portion of the background literature. The dramatic (and statistically significant) differences in the 2014−2016 final introductions versus the 2013 final drafts (Figure 1) stem from some combination of (1) increased guidance, (2) requirement that all students complete all drafts, (3) increased student buyin as the drafting system was no longer new, and (4) improved C

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initial drafts in 2014−2016. When looking at the initial drafts in 2013, many of them are visibly token efforts, with students knowing they had time to fix it later. The initial drafts in 2013 included fewer citations to the primary literature than the “only drafts” in 2012, at a statistically significant level. The dip in citations is a reasonable proxy for the level of time and/or effort that students had invested in learning the background of the project up to that point. Starting with the 2014 cohort, students explicitly were made aware that it was in their best interests to submit what they considered to be a “final” draft of the introduction for their first attempt, which would then be improved in light of faculty feedback. The exhortation was taken seriously by most students, as evidenced by citations of the literature returning to, or slightly exceeding, the 2012 baseline levels (Figure 1). Presumably, students did the best that they were able to do when writing a single draft in 2012, so a return to those levels suggests that students were exerting the maximum effort that can reasonably be expected from them in 2 weeks. The most significant oversight in the 2012 prompt for the introduction was that no mention was made of including figures. As a result, only 11/55 students in the 2012 cohort’s single drafts included visual aids at all, and those that did seemed to use the visuals largely to decorate the text rather than as integrated, essential parts of the narrative. In no cases did students have multiple visual aids, nor were there any attempts to have the visual aids tell a stand-alone story, even though figures and schemes in the literature are often designed to do so. The secondary goal when implementing the drafting process was to require students to prepare more figures, and to have those figures be attractive and effective as visual aids, capable of carrying the narrative alone, and be well-integrated into and supported by nearby text (Figure 2). Figure 2 reveals a statistically significant increase in the number of figures included in the final draft of the introduction, relative to initial submissions. There was no statistical difference between 2012 and the first draft of 2013, which makes sense in light of the traditional student behavior of submitting the first draft written. Of rather more interest is the fact that, from 2014 on, the number of visual aids included in the first draft was statistically different from 2012 and 2013. By 2014, the message that students must include visual aids in their introductions had clearly been heard in prelab lectures and read in the prompts for the assignment (see the Supporting Information). The raw number of visual aids included would be largely irrelevant if they were of poor quality. When investigating the quality of the submitted figures and schemes, visual aids were counted as “publication worthy” when they were structurally correct, attractively laid out, well-formatted, informative in their captions, and relevant to the text (Figure 2). Visual aids, like other forms of writing, dramatically improve with focused practice and drafts. It should be noted that the first drafts of the introduction have always (starting in 2013) been submitted prior to the figure and scheme assignment that stresses what a good visual aid entails (Table 1). The suggestive, but not statistically significant, increase in publication quality figures in the first drafts in 2014−16 relative to earlier cohorts may represent students’ increased familiarity with the literature prior to attempting their first draft of their own introductions, which would correlate with the increased citation counts on the first drafts in 2014−2016 relative to 2013 (Figure 1). Though students can cite the literature without reading or understanding it, the improved quality of visual aids suggests

Figure 2. An analysis of variance showed that that the effect of requiring multiple drafts of students’ introductions on total figures present was significant, F(4, 280) = 163.5, p ≪ 0.01. Post hoc analyses (Tukey−Kramer) revealed that all pairwise comparisons were statistically significant save the only drafts in 2012 (pale purple) and first drafts in 2013 (pale red). An analysis of variance showed that that the effect of requiring multiple drafts of students’ introductions on the number of publication worthy figures included was significant, F(4, 280) = 89.1, p ≪ 0.01. Post hoc analyses (Tukey−Kramer) revealed that final drafts (bright blue) were statistically different from initial drafts (bright red), but that the differences between first drafts in 2014−16 and the other first drafts did not reach significance. *In 2013 students were allowed to opt out whenever they pleased, with 32/43 completing all four drafts. The 2013 data were extracted from the last draft submitted for all 43 students.

that students were extracting the crucial information from these articles. Taken together, the improved figures and substantially increased numbers of references reveal that the student conception of an introduction section was transformed. Whereas initial student introductions relied primarily on prelab lectures or the lab manual as the source material, by the end students recognized the need to visually describe many key findings from the primary literature, and to rely exclusively on the primary literature for their claims.

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CONCLUSIONS In a lab setting focused on standalone experiments, it is only natural that student writing will be assessed largely via one-off assignments. Because the focus here was on a single project for 10 full weeks, multiple drafts of individual subsections were required, as much as was feasible and appropriate for the project. When the standalone experiments were replaced with a long-term project, a serious mistake was made initially by simply assuming that the writing of subsections of the final paper throughout the semester would offer a fundamentally different and better experience for students. Though the assignments were intrinsically linked, students’ unfamiliarity with the specific demands of journal-style chemistry writing ensured that students experienced them more as thematically linked one-off assignments rather than as parts of a coherent whole. Though there was merit and value in exposing students to the breadth of writing styles necessary to build a full paper, an opportunity to achieve depth had been lost, and a shift was made to the drafting system for subsequent cohorts. Requiring students to revisit their own work and improve it in light of feedback is incredibly valuable. Given the specific project, the focus was on the introduction subsection, even if it D

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HDACi project and an NSF-TUES grant (DUE-1044396) to implement the HDACi project in the teaching laboratory.

required paring back the focus on other traditionally important subsections such as the results and discussion section. Over the course of four drafts, the student conception of what an introduction should look like for an organic synthesis was transformed. The number of references included was dramatically higher, which seemed to indicate increased student engagement with the literature. The increased number and quality of visual aids included in the introductions was also striking. In the end, the best students were able to approximate a good introduction from the primary literature, even though no one started their journey close to that benchmark. The weaker students were able to transform their writing by including appropriate visual aids and relying on the literature more heavily. All students were able to mimic the style of introductions in the synthetic literature, with the primary difference between stronger and weaker papers being students’ command of the project. Though implemented in the context of a semester-long organic project, the idea to focus on a specific piece of writing with multiple drafts can be modified and implemented more broadly across the curriculum. All that is required to implement a drafting system is a willingness to forego the assignments that end up replaced! Smaller drafting exercises can be incorporated wherever opportunities are present, writing workshops can be implemented in the laboratories to require additional drafts of formal writing assignments, and the idea of multiple drafts has been expanded into nonwriting activities.38

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(1) Calandra, N. A.; Cheng, Y. L.; Kocak, K. A.; Miller, J. S. Total Synthesis of Spiruchostatin A via Chemoselective Macrocyclization using an Accessible Enantiomerically Pure Latent Thioester. Org. Lett. 2009, 11 (9), 1971−1974. (2) Insisting upon the phrase in strict order (including the quotation marks on “project based learning”) still yields 33 hits in this Journal, as well as 16 book chapters reviewing the concept. (3) Clark, T. M.; Ricciardo, R.; Weaver, T. Transitioning from Expository Laboratory Experiments to Course-Based Undergraduate Research in General Chemistry. J. Chem. Educ. 2016, 93 (1), 56−63. (4) Tomasik, J. H.; Cottone, K. E.; Heethuis, M. T.; Mueller, A. Development and preliminary impacts of the implementation of an authentic research-Based experiment in General Chemistry. J. Chem. Educ. 2013, 90 (9), 1155−1161. (5) Slade, M. C.; Raker, J. R.; Kobilka, B.; Pohl, N. L. B. A Research Module for the Organic Chemistry Laboratory: Multistep Synthesis of a Fluorous Dye Molecule. J. Chem. Educ. 2014, 91 (1), 126−130. (6) Murthy, P. P. N.; Thompson, M.; Hungwe, K. Development of a Semester-Long Inquiry-Based Laboratory Course in Upper-Level Biochemistry and Molecular Biology. J. Chem. Educ. 2014, 91 (11), 1909−1917. (7) Winkelmann, K.; Baloga, M.; Marcinkowski, T.; Giannoulis, C.; Anquandah, G.; Cohen, P. Improving Students’ Inquiry Skills and Self Efficacy through Research-Inspired Modules in the General Chemistry Laboratory. J. Chem. Educ. 2015, 92 (2), 247−255. (8) Evans, H. G.; Heyl, D. L.; Liggit, P. Team-Based Learning, Faculty Research, and Grant Writing Bring Significant Learning Experiences to an Undergraduate Biochemistry Laboratory Course. J. Chem. Educ. 2016, 93 (6), 1027−1033. (9) Kerr, M. A.; Yan, F. Incorporating Course-Based Undergraduate Research Experiences into Analytical Chemistry Laboratory Curricula. J. Chem. Educ. 2016, 93 (4), 658−662. (10) Hulien, M. L.; Lekse, J. W.; Rosmus, K. A.; Devlin, K. P.; Glenn, J. R.; Wisneski, S. D.; Wildfong, P.; Lake, C. H.; MacNeil, J. H.; Aitken, J. A. An Inquiry-Based Project Focused on the X-ray Powder Diffraction Analysis of Common Household Solids. J. Chem. Educ. 2015, 92 (12), 2152−2156. (11) Kiefer, A. M.; Bucholtz, K. M.; Goode, D. R.; Hugdahl, J. D.; Trogden, B. G. Undesired Synthetic Outcomes During a Project-Based Organic Chemistry Laboratory Experience. J. Chem. Educ. 2012, 89 (5), 685−686. (12) Kerr, M. A.; Yan, F. Incorporating Course-Based Undergraduate Research Experiences into Analytical Chemistry Laboratory Curricula. J. Chem. Educ. 2016, 93 (4), 658−662. (13) Evans, H. G.; Heyl, D. L.; Liggit, P. Team-Based Learning, Faculty Research, and Grant Writing Bring Significant Learning Experiences to an Undergraduate Biochemistry Laboratory Course. J. Chem. Educ. 2016, 93 (6), 1027−1033. (14) Horowitz, G. The State of Organic Teaching Laboratories. J. Chem. Educ. 2007, 84 (2), 346−353. (15) Brownell, S. E.; Kloser, M. J.; Fukami, T.; Shavelson, R. Undergraduate biology lab courses: comparing the impact of traditionally based “cookbook” and authentic research-based courses on student lab experiences. J. Coll. Sci. Teach. 2012, 41 (4), 36−45. (16) Meyers, J. K.; LeBaron, T. W.; Collins, D. C. The Journal of Kitchen Chemistry: A Tool for Instructing the Preparation of a Chemistry Journal Article. J. Chem. Educ. 2014, 91 (10), 1643−1648. (17) The WAC Clearinghouse Home Page at Colorado State University. http://wac.colostate.edu/index.cfm (accessed July 2017). (18) Kovac, J.; Sherwood, D. W. Writing across the Chemistry Curriculum: An Instructor′s Handbook; Prentice Hall: Upper Saddle River, NJ, 2001. (19) Moore, R. Writing as a Tool for Learning Biology. BioScience 1994, 44 (9), 613−617.

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.7b00135. Current writing prompts, the initial 2012 writing prompts (for comparison), the syllabus (for timing), and the current rubrics for each assignment; series of emails that have served as scaffolding for students, written in response to the collective errors after each round of the 2013 drafts was graded; “answer key” that was generated after all four drafts in 2013 had been submitted; and the progression that students typically follow on this assignment over time is described, with examples of “publication worthy figures” as well as the types of errors expected. (ZIP)

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REFERENCES

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

David J. Slade: 0000-0002-6861-061X Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS Thanks to Eric Barnes, Philosophy, for the idea and some helpful conversations, as he has used this to good effect in his own courses. Thanks to Jennifer Luft (Keck Science Department of the Claremont Colleges) for the initial paper prompts. One of the authors (J.S.M.) gratefully acknowledges funding from an NIH-AREA grant (1R15CA152869-01) for the E

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