Formalizing the First Day in an Organic Chemistry Laboratory Using a

Activity pubs.acs.org/jchemeduc

Formalizing the First Day in an Organic Chemistry Laboratory Using a Studio-Based Approach Christina G. Collison,* Jeremy Cody, Darren Smith, and Jennifer Swartzenberg Department of Chemistry, Rochester Institute of Technology, Rochester, New York 14623, United States

Downloaded by UNIV OF CALIFORNIA SANTA BARBARA on August 25, 2015 | http://pubs.acs.org Publication Date (Web): August 11, 2015 | doi: 10.1021/acs.jchemed.5b00226

S Supporting Information *

ABSTRACT: A novel studio-based lab module that incorporates studentcentered activities was designed and implemented to introduce second-year undergraduate students to the first-semester organic chemistry laboratory. The “First Day” studio module incorporates learning objectives for the course, lab safety, and keeping a professional lab notebook.

KEYWORDS: Second-Year Undergraduate, Organic Chemistry, Laboratory Instruction, Inquiry-Based/Discovery Learning, Student-Centered Learning, Laboratory Management, TA Training/Orientation

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RATIONALE There is one lab exercise that is not universally supplied by a textbook and that is often delivered unequally among lab sections: The first day of lab.1 Given that the organic lab is early in an undergraduate’s career, there is a substantial amount of information about lab operations, safety protocols, and lab objectives that needs to be conveyed. The organic chemistry lab is also one of the more potentially hazardous labs delivered to undergraduates. Add to that the fact that so many universities rely on graduate teaching assistants (TAs) to teach these labs. Given these circumstances, the coordinating instructor is faced with a challenge of relaying this enormous amount of information to the lab TAs such that they can uniformly relay the information to the undergraduates in their lab without the prompt of a lab text. Thus, how can the relay of knowledge from TA to undergraduate regarding the first-day material become standardized? This question is what prompted us to design a workshop-style activity for the first day of an undergraduate organic chemistry lab. Our approach to the organic sequence of laboratories is to generate engaging studio-based experiments2 that differ from the traditional expository experiments where the students follow the prescribed directions and race out of the laboratory as soon as possible, never fully understanding the point of the exercise.3 Extending this lab delivery in a formalized first-day activity made sense. Traditionally, our instructors would go through the rules, the syllabus, and notebook setup with undergraduate students in a manner that invariably dictated to students in lab (sage on the stage). This passive manner, with which to convey very important information, proved ineffective, © XXXX American Chemical Society and Division of Chemical Education, Inc.

and did not guarantee that each point was communicated. Additionally, it set the wrong tone for future lab exercises in that only 1−1.5 h of the 3- or 4-h lab time was used. From day one, students expected to leave early. To ensure that the material was getting disseminated thoroughly and equally among various lab sections, that an appropriate amount of time was spent on the material, and that the students were taking an active-role in learning about organic lab operations, a first-day workshop activity was implemented.

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IMPLEMENTATION The first-day lab activity is delivered in either a 3- or 4-h time frame and is a formal eight page document (see Supporting Information) distributed to students when they arrive on the first day in the introductory organic chemistry I lab. To manage lab time, students work in pairs, and it is recommended that the first task is to assign a workstation to each student and have them identify their lab partner. Once established, the instructor can introduce themselves and pass out the worksheets. The Syllabus

The first pedagogic opportunity is engaging students with the course objectives. Prior to passing out the lab syllabus, students are asked to work with their partners to discuss what they think the purpose is for taking this lab. This short exercise is premised by the concept of a student-directed syllabus.4 Although the syllabus is already set, students must work with a partner and predict the learning objectives for the lab. The

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DOI: 10.1021/acs.jchemed.5b00226 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

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notebook entry mirrors the scientific process. As such, the worksheet first allows students to review the scientific method and then guides them through correlations between the scientific method and notebook setup. Additionally, an activity using a broken flashlight was adapted in order to reinforce the concept of changing variables in an experiment and the care a student must take when drawing conclusions.5 To demonstrate the importance of maintaining a legible and accurate account of lab experiments, the following activelearning exercise (FACE) is done: 1. On a sheet of paper, each student writes his/her name at the top and draws a face in the center of the page titled ORIGINAL. 2. A second sheet of paper is distributed and each student writes his/her name at the top, followed by a detailed list of instructions so as to guide someone else to draw the same face without actually seeing the illustration. 3. All papers are collected and only the INSTRUCTIONS are randomly redistributed to students along with a third clean sheet of paper entitled COPY. Each student must write his/her name on the copy sheet as well as the original artist’s name in the indicated spaces, and follow the instructions given to draw a face on the copy sheet. 4. All copies are collected and matched with their original, often to the amusement of students in the class. When the drawings were close enough, students decided that the result was pretty close to what was intended and agreed that this is akin to being able to duplicate a reaction in the lab (Figure 1a). Over the years, however, a variety of mishaps have

syllabus is then passed out, and the objectives on the syllabus are compared to the objectives determined by the students. Student Curiosity


A second pedagogic opportunity is to allow students to explore the lab and ask questions. Students are encouraged to look around and come up with any questions they may have about the physical lab itself. The most common questions involved the function of the hoods, what kind of experiments would be run, where the chemical safety information could be found, whether the lab experiments would be dangerous, whether there would be a lecture part to lab for explanations, and what the function was for different benchtop equipment. The questions often led to health and safety issues that students raised as their greatest concern. As such, this discussion naturally segues to the safety portion of the worksheets. Lab Safety

The next activity involves drawing a map of the lab on the first page of their lab notebook. The map should include the location for the following: • Your Workstation • All Fire Extinguisher(s) • All Exits • Safety Shower(s) • First Aid Kit • Chemical Spill Kit • Waste Accumulation Area(s) • All Eye Wash Stations • SDS (Safety Data Sheets) • Chemical Storage Areas • All Balances • Glass Waste Container • Any Instrumentation The process of drawing this map in a notebook improved the working environment come the first day of a lab experiment and triggered additional safety questions by students. The second safety activity has students propose a pro and a con for each of the listed lab safety rules. For example, the most widely given pro for wearing lab goggles was to protect your eyes from a chemical splash. Some of the responses given for why wearing lab goggles might be a con were that they can fog up, might be uncomfortable, or may not fit well over glasses. This simple and quick activity had students engaged in the safety discussion and circumvented the TA passively reading off the list of lab safety rules. Students expressed that they innately knew that the lab rules are implemented for their best interest and safety, but the reason/pro for some lab rules were not necessarily obvious to students, thus invoking a discussion. Lab Notebook

At RIT, organic chemistry I is taught in the second semester to first-year undergraduate chemistry majors. As such, students have had very little experience in a lab setting and few have begun independent research in a lab. Thus, they have little understanding of the importance of maintaining a professional lab notebook and its correlation to problem-solving using the scientific method. Most lab experiments delivered to introductory undergraduate organic chemistry students are designed with the scientific method in mind, yet students often fail to see any relationship, and invariably treat the scientific method and the process of conducting a lab experiment in the course as unrelated. The goal was to convey the importance of writing in a lab notebook and to correlate how a typical lab

Figure 1. Results from the original and replicate drawings for the FACE exercise.

occurred. For example, most students fail to indicate the gender intended, and the original and copy look more like a brother and a sister. One time, a student drew the face of a horse since “human face” was not specified in the directions and then failed to write horse face in the instructions. Examples of such differences and the related take-home messages are shown in Figure 1. B



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PEDAGOGIC GOALS

out of the lab activity well informed about the lab objectives and safety practices, and with an appreciation for maintaining a professional notebook. The formalized first-day activity has both removed the stress from our instructors who must coordinate lab TAs to convey this first-day material and has assured a balanced and complete coverage of lab information across all lab sections. Additionally, the use of the entire lab period on the first day sets the tone for future labs; it is not a race to get the labs done and get out of lab as quickly as possible. Partner work and class discussions as a whole set the pace for the lab time. Students came in the following week expecting more of the same and taking full advantage of every minute spent in the lab. This self-discovery studio activity aptly augments our previously published studio-based modules,3 as well as our technique-focused modules to follow.

Engaging Students with the Course Objectives

Although the syllabus is already set, having students predict the learning objectives for the lab reinforces the concepts, as well as instills more ownership of what is to come. Exploring the Lab and Asking Questions

Allowing the students to physically walk around the lab on the first day was critical to opening a discussion on lab safety. The worksheet prompts encourage an open dialogue and help students understand that they are not alone in their concerns. The lab map and lab safety exercises both reinforce major concepts while establishing a safe environment in which to ask questions.

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Understanding the Important Role of Lab Notebooks

The pedagogic value for the FACE exercise comes from tangible talking points that directly relate to the process of running reactions in the lab. The conveyed bottom line is that it can be very difficult to forge ahead to discover and document NEW chemical transformations, but it can also be frustratingly difficult to REPLICATE known work. A few take-home messages were the following: • Details matter. Inadvertent omissions and lack of specific details can lead to drastically different results. Was the product a solid or a liquid? What color was it? These visual properties are often left out of a lab writeup. • Misinterpretation. Was it the author who wrote the experimental poorly or a misinterpretation by the scientist replicating the work? • Legibility. Some students complained that they could not read the hand-writing. As a research student, one may be tasked to repeat the experiment of a lab mate. Often times, one of your own experiments must be repeated that may have been done over a year ago. Being able to follow someone else’s entry or even your own is important, especially when the work is ready for dissemination. Students are reminded that the instructor must also read and grade lab notebooks and, if it is not legible, how might this be reflected in one’s grade? • Timely record keeping. As a follow-up, students are asked in a subsequent week’s lab to draw the same face they drew on day one without their instructions. Most students could not remember what they drew and we reminded them of the need to record experimental steps in their lab notebook in real time and not in their dorm room the following week.

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.5b00226. Lab activity worksheets for students (PDF, DOC) Instructor guide that includes characteristic answers (PDF, DOC) Face sheet 1, ORIGINAL template for the FACE exercise (PDF, DOCX) Face sheet 2, INSTRUCTIONS template for the FACE exercise (PDF, DOCX) Face sheet 3, COPY template for the FACE exercise (PDF, DOCX)

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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 We would like to acknowledge our funding from the National Science Foundation (TUES-1245160). We also thank Brian Edelbach and Jason Anderson of Monroe Community College for their valuable feedback during the development of this lab activity.

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REFERENCES

(1) Examples of first-day laboratories involving a wet chemistry experiment: (a) Hermann, C. K. F. First Day in Organic Lab. J. Chem. Educ. 1996, 73 (9), 852−854. (b) Shugrue, C. R.; Mentzen, H. H., II; Linton, B. R. A Colorful Solubility Exercise for Organic Chemistry. J. Chem. Educ. 2015, 92 (1), 135−138. (2) (a) Oliver-Hoyo, M. T.; Allen, D. A.; Hunt, W. F.; Hutson, J.; Pitts, A. Effects of an Active Learning Environment: Teaching Innovations at a Research I Institution. J. Chem. Educ. 2004, 81 (3), 441−448. (b) Gottfried, A. C.; Sweeder, R. D.; Bartolin, J. M.; Hessler, J. A.; Reynolds, B. P.; Stewart, I. C.; Coppola, B. P.; Banaszak Holl, M. M. Design and Implementation of a Studio-Based General Chemistry Course. J. Chem. Educ. 2007, 84 (2), 265−270. (c) Altmiller, H. Another Approach to Freshman Chemistry. J. Chem. Educ. 1973, 50 (4), 249. (d) DiBiase, W. J.; Wagner, E. P. Aligning General Chemistry Laboratory with Lecture at a Large University. Sch. Sci. Math. 2002, 102 (4), 158−171. (e) Bailey, C. A.; Kingsbury, K.; Kulinowski, K.; Paradis, J.; Schoonover, R. An Integrated Lecture-Laboratory Environment for General Chemistry. J. Chem. Educ. 2000, 77 (2), 195−199.

Setting the Tone for Lab Module Instruction

The pedagogic opportunity to set the tone for the semester with regard to the lab modules used for instruction is demonstrated outright on day one. With the use of a worksheet-style akin to other labs in the curriculum,3 the practice of partner work and class discussions as part of the iterative learning cycle were more readily accepted since the tone was set early. Additionally, the FACE exercise served as an ice-breaker for students and TA to get to know one another, laugh a little, and learn something at the same time.

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SUMMARY The instructional method described takes a mundane and passive laboratory session and engages students in activities that prepare them for the upcoming lab experiments. Students come C



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(g) Apple, T.; Cutler, A. The Rennselaer Studio General Chemistry Course. J. Chem. Educ. 1999, 76 (4), 462−463. (3) (a) Collison, C. G.; Cody, J.; Stanford, C. An SN1-SN2 Lesson in an Organic Chemistry Lab Using a Studio-Based Approach. J. Chem. Educ. 2012, 89 (6), 750−754. (b) Cody, J. A.; Craig, P. A.; Loudermilk, A. D.; Yacci, P. M.; Frisco, S. L.; Milillo, J. R. Design and Implementation of a Self-Directed Stereochemistry Lesson Using Embedded Virtual Three-Dimensional Images in a Portable Document Format. J. Chem. Educ. 2012, 89 (1), 29−33. (4) (a) Hudd, S. S. Syllabus Under Construction: Involving Students in the Creation of Class Assignments. Teaching Sociology 2003, 31 (2), 195−202. (b) Gibson, L. Student-Directed Learning: An Exercise in Student Engagement. College Teaching 2011, 59 (3), 95−101. (5) Kazilek, C. J.; Pearson, D. Using the Scientific Method To Solve Mysteries. http://askabiologist.asu.edu/explore/using-scientificmethod-solve-mysteries (accessed Sep 2014).

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Formalizing the First Day in an Organic Chemistry Laboratory Using a

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