POGIL Laboratory Experiments Place Date Facilitator(s) Have participants sit in groups of 3 unless you have more than 18 people. You want as many groups as you can up to 6. Make groups heterogeneous; make sure that chemists are distributed among all of the groups as possible. Probably the most important factor in groups is to have the chemists distributed as widely as possible, with at least one chemist in each group if possible. Assign roles: Manager, Recorder, Presenter [Encourager (tells people when they are doing a good job) if necessary] Remind people of the purpose of he session: to introduce them to the main ideas and principles of POGIL Lab.

Activity 1: Your Laboratory Experiences Take out a piece of paper Divide the paper in half, labeling one half “Successful” and the other half “Horrible” Ask participants to pull out a piece of paper, letting them know this is “just for you”, and will be used to stimulate discussion Divide the paper in half w/ the successful/horrible headings. Note: this activity could be done w/o this and the next slides, if the facilitator is comfortable giving verbal instructions that aren’t backed up by slides.

Consider All Your Laboratory Experiences as a Student and as an Instructor Individually: Identify a specific course-related laboratory experiment that was very successful, describe the experiment, and list three things that made it “successful.” Identify a specific course-related laboratory experiment that was horrible, describe the experiment, and list three things that made it “horrible.” (3 min) Ask people to identify 3 things and let them know they’ll have 3 minutes. While people are working individually, this can be a useful time to circulate and look over shoulders. What they write and how engaged they are with the activity can be helpful to get a sense of the room and what kind of personalities are there. This kind of info can inform strategies that might be used/modified throughout the day.

Common Laboratory Experiences Discuss your “successful” and “horrible’ laboratory experiments within your group. Try to find any common characteristics. Identify three significant characteristics (preferably that you have in common) for the successful experiments and three significant characteristics for the horrible experiments. Be prepared to report out your list. [7 min] Warning: frequently participants just like to talk about this (and could talk about it for more than seven minutes). Seven minutes is really not a long time for this step. It makes people feel good about the beginning of the workshop. Individuals will think about specific experiments but when they make the group list encourage them to generalize.

Reporting Out Record at the board; can be referred to later in the presentation when looking at POGIL criteria. Make sure that this is posted somewhere that will stay for the entire session. If two facilitators, one can record while other facilitates.

Activity 2: A POGIL Laboratory Experience At this point, set the stage by telling people where this particular laboratory exercise comes from. (e.g., it is used in organic at Washington College and in gen chem at F&M). The whole laboratory can be completed in 3 hours, but for the purposes of the workshop, we’ll be doing parts to illustrate the flow of the lab. WE WILL NOT BE GOING TO AN ACTUAL LAB. This is not the ONLY valuable way to do lab. Will briefly discuss SWH later, but there are other approaches that are important and valuable for students. But this session is about what is considered a POGIL lab by The POGIL Project.

Question of the Day: How is the structure of a molecule related to its boiling point? Boiling point can be thought of as a measure of the strength of attractions between molecules in a liquid. Some potentially useful information Compound Molecular Formula Structural Formula MW BP (oC) octane C8H18 114 126 2-butanol C4H10O 74 100 You may want to toggle back and forth between this slide and the next one so that people are reminded of the task and also can see this data When the time is up from the next slide (2 minutes individual and 3 minutes in a group discussing possible relationships) go to the following slide to report out. STUDENT BACKGROUND KNOWLEDGE: Lewis structures and possible shapes Bonding:relative lengths and strengths of single and double bonds Molecular weight Electronegativity Maybe dipole moment BUT NOT IMFs; THEY SHOULD ASSUME THAT THE STUDENTS DO NOT KNOW ABOUT IMFs AT THIS POINT.

Question of the Day: How is the structure of a molecule related to its boiling point? Boiling point can be thought of as a measure of the strength of attractions between molecules in a liquid. Individually list five relationships between molecular structure and boiling point. (e.g., the larger the X, the higher the boiling point; the more Y, the higher the boiling point; the longer the name, the higher the boiling point, etc). [2 min] Within your group your manager will lead a discussion of your lists and the preparation of a prioritized list of these relationships. Your presenter will be called upon to report out your results. [3 min] Tell chemists who are participating to provide answers they think their students would give (that’s different than acting as a student). Others can give their own ideas. Tell the attendees that the students in a real lab may (or may not) have been assigned some reading in advance and know that during the lab period they would be measuring boiling points using a distillation apparatus. The workshop attendees do not have to use the data on n-octane and 2- butanol. There are only two data points provided and that is intentional since two are not enough for a trend line.. In general, they should have proposed relationships that are identifiable as STRUCTURE, not the results of structure (like imfs). As you facilitate this session you would perhaps need to intervene to make sure that the focus is on the structure of the molecule and not on some consequence of that such as intermolecular forces –particularly for chemists Emphasize that everyone in each group should try to come up with five relationships.

Question of the Day: How is the structure of a molecule related to its boiling point? Reporting Out After the appropriate time, have the presenters report out their prioritized list of relationships. You may have to make their relationship statements more succinct than what they state for recording on the board. Once the groups propose answers to the QOD you would use the next slide to illustrate the kinds of answers students have proposed over the many years we have used this experiment (in Gen Chem at F&M and in Organic at Washington College).

Question of the Day: How is the structure of a molecule related to its boiling point? Typical student responses Molecular weight Shape Size Kind of atoms Strength of bonds Number of atoms Number of bonds Types of bonds What experiment(s) would need to be conducted to test these hypotheses? What apparatus and what reagents would be needed? You need to remind those in the workshop that students would come to lab not knowing the QOD but may have read an assignment in the lab manual providing a description of boiling point and the apparatus used for obtaining such. What are you going to do? Who is going to do it? What is needed to do it? If you haven’t mentioned it yet, explain that the students would have a detailed explanation of a distillation apparatus and how to set it up – or some other process for measuring boiling point.. They know they will be measuring boiling point (via distillation) for some liquid. TELL PARTICIPANTS THAT WE ARE TAKING A SHORT CUT HERE. TYPICALLY THERE WOULD BE A DISCUSSION WITH STUDENTS THAT RESULTS IN THE DECISION TO MEASURE BOILING POINTS OF SEVERAL LIQUIDS. HERE WE GO DIRECTLY TO IMPLEMENTING THE DATA COLLECTION IN ORDER TO SAVE TIME HERE.

Boiling Points of Liquids Group #1 Group #2 Group #3 (hydrocarbons of varying length) (hydrocarbons of varying length with OH) (hydrocarbons of varying length with C=O) pentane 1-propanol acetone hexane 1-butanol butanone heptane 1-pentanol 3-pentanone decane 1-hexanol 2-heptanone Group #4 Group #5 Group #6 (4 or 5 carbons; 1st 3 nearly identical MW) (5 or 6 carbons; last 3 almost identical MW) (first pair, last pair: almost identical MW) pentane acetone 1-butanol hexane 1-propanol butanone 3-pentanone 1-pentanol Hand out the group assigned liquids (data sheet 1) to the managers, ask the manager to distribute to each group member. MAKE SURE THAT GROUPS 1, 2, 3, and 4 are distributed. Especially GROUP 4! Because GROUP 4 sets up discrepant event (as do 5 and 6) At this point, student groups in the real laboratory setting would know what their compounds are but would not know what molecules the other groups have. At this point you would explain that this is an illustrative listing of the liquids to be examined. For a chemistry class, students may write these structures as part of a pre-lab assignment, so it doesn’t take them long to generate the structures. Even if they do it at this point, it doesn’t take much time because they are already familiar with Lewis structures and naming of simple organic compounds. Now, within your group, make a prediction about the bp’s – their values/expected trends and agree about the justification for your prediction. It is important that students make an intellectual commitment to specific outcomes so that they’ll know whether or not what they predicted actually happens. They need to recognize when something unexpected happens. At this point in a real laboratory, the instructor would check the structures and look at student predictions, before letting them begin the experiment. The instructor also would approve the apparatus to be used. So now we’re going to pretend that you have done the experiment and you have the data. Go to next slide(Pass out the data – Voila!)

Analysis of Your Group Data Examine the data in your group and determine if there are any trends. If so, discuss what those trends mean. Which one of the possible hypotheses seems most likely based solely from your group data? Which of the possible hypotheses can be rejected based solely from your group data? [5 min] At this point the workshop facilitator would hand out the data (if not already done so). Give participants about 5 minutes to work through this. Emphasize that they should be drawing conclusions based SOLELY on their own data. Have participants report out their conclusions and post those along with the previously posted hypotheses (which are most likely, which are rejected) Start with Group 1 and go in order. Once discrepant info is provided by Group 4, have groups describe what compounds they had. Or could toggle back to slide 11. This is important because groups only have their own data in front of them, and can’t remember what the other groups had Based on these discussions, it is likely that Groups 1 – 3 will say that the most likely hypothesis is the one that says that BP is related to MW; groups 4 – 6 will have said that should be rejected based on their data…..so, can show this with next four slides… If relevant point out how rich it is to discuss the data in this way.

Analysis of Group Data This slide, along with the next few, present the bp data from the results. These can be shown relatively quickly as a way of showing

Analysis of Group Data Group 2 also thinks that bp increases with MW

Analysis of Group Data Group 3 also thinks that bp increases with MW

Analysis of Group Data Group 4 has data that suggest that this trend is NOT valid in general. The point here is to emphasize that combining all of the class data enables a better sense of the overall picture. Conclusion from all of the data: For a given type of molecule, bp increases with MW. However, for a given MW, there can be a wide range of bps. However, bp (alkane) <bp (ketone) <bp (alcohol) for a given MW There are reasons related to molecular structure that account for this pattern, and also to why bp increases with MW (for hydrocarbons). No need to go into detail especially if some non-chemists are present. Main point is that trend can be uncovered and hypotheses tested.

Possible Further Extensions Use molecular modeling to investigate relationship of structure to dipole moments and boiling point. Predict (and measure) the boiling points of other liquids. Note that 2-butanol (100°) and 1-butanol (112°) have different boiling points. Is this a general difference between 1- and 2- alcohols? How does placement of the OH group influence boiling point? These are some possible further extensions of this experiment, applying the ideas that have been developed to new situations. For chemists, can also mention that this experiment can be used as an introduction to a discussion of intermolecular forces. Clearly the specific concepts of dispersion forces, dipole-dipole forces, and hydrogen bonding can’t be developed from this data, but students can recognize that the presence of a dipole moment increases bp and also that there is something “special” about the presence of OH vs. C=O.

Student Outcomes As a group: Identify one laboratory skill that is developed and one content learning objective for the boiling point experiment. [2 min] This may take less than 2 minutes. Probably no need to have all groups report out once the main ideas have been established. Lab skill: measuring boiling point, etc. Content learning objective: bp increases with MW for a given type of molecule; for a given MW, bp(alcohol)>bp (ketone) > bp (alkane) THE POINT IS NOT TO GRADE THEM ON HOW CLOSE THEY ARE TO THE CORRECT BOILING POINT, BUT RATHER ON HOW THEY ANALYZE AND PRESENT THEIR RESULTS.

The POGIL Laboratory Experience What distinguishes a POGIL laboratory experience from a traditional laboratory experience? This is an important slide and question to ask and leads to the answer that is shown on the next slides. This presentation is based on the assumption that the participants have been introduced to POGIL previously – either earlier at this workshop or at a previous workshop. In particular, it is assumed that they have been introduced to the Learning Cycle previously. If this is not the case, then an introduction to the Learning Cycle should take place - either immediately after this slide, or later in the discussion

The Traditional Laboratory In many traditional laboratory settings, a concept that has been previously introduced in class, or presented as part of the pre-lab preparation, is confirmed or verified through the “experiment.” Use this to ground people in thinking about the standard lab

Distinguishing Characteristics of “Verification” Laboratories Identified by College Chemistry Students The instructor is concerned with the correctness of data. The instructor lectures the whole class. During laboratory the students record information requested by the instructor The laboratory experiments develop skill in the techniques or procedures of chemistry. Students usually know the general outcome of the experiment before doing the experiment. Abraham, M.R. (1982). A descriptive instrument for use in investigating science laboratories. Journal of Research in Science Teaching, 19(2): 155–165 Use this to inform participants about the fact that there has been some scholarship around the issue of laboratory format. Chem Ed researchers have identified some features that tend to characterize these verification laboratories. Emphasize that students identified these characteristics, not instructors Comment about the reason the year of the publication is highlighted -- this issue about laboratory format has been going on a long time BRIEF DESCRIPTION OF RESEARCH: two groups of students in general chemistry course at large university had different types of laboratory experience: verification and discovery. After a semester of these experiences, they were given 25 statements about laboratory experience, and sorted these statements into 5 groupings that were related to how well the statement described their laboratory experiences (something like: not at all (lowest group) to very descriptive (highest group). The number of statements in each group was also specified: 3, 5, 9, 5, 3 so that three statements must be given the highest rating, 5 the next highest, 9 in the middle, etc. The listed characteristics are the ones that were rated higher with statistical significance by the group of students who had verification laboratory experiences for the semester.

The POGIL Laboratory Laboratory work is performed in advance of classroom work on underlying principles (limited background). Students work in self-managed teams to conduct experiments rather than exercises that verify previously taught principles. During a pre-lab session (real and/or virtual) the instructor poses a focus question or Question of the Day (QOD) and students propose a set of tentative answers. Students do NOT all perform the identical experiment Data is combined from multiple students to uncover general trends or concepts, and address the QOD. QOD = Question of the Day

Pre-Lab Session Provides focus and structure; gets everyone involved Focus question (Question of the Day) Solicit hypotheses or predictions from students Discuss appropriate experiments What is expected for each hypothesis Those of us who use this approach in lab believe that the pre-lab session is one of the most important components of the lab. It allows students to acquire some ownership and investment in the outcome. As the first bullet states, it gets everyone involved and the best time for that is in the beginning. POGIL labs depend on the structure of groups to facilitate each member being involved in discussing the QOD It is important for students to understand that the QOD will be answered when EVERYONE has finished the laboratory experience. Unlike other lab structures, in which students answer a question independently, students in a POGIL lab can’t adequately answer the question without data from others. Students will be engaged in coming up with tentative answers to the QOD and ideas about appropriate experiments An important component of this part of the experience is for students to make an intellectual commitment to a particular outcome so they’ll recognize whether what they think happens actually does happen or doesn’t

Data Collection Students collect data, with different students measuring related phenomena but with appropriate variations to address the QOD. Guided inquiry questions during the data collection phase may help students think about the implications of their results. Some duplication of conditions between students can be desirable to check for reproducibility and reliability of results. Typical “variations”: different temperatures, concentrations, other initial conditions, substrates, etc. Can point out that in the bp experiment, several groups were assigned the same liquid; this provides a sense of how much variation there can be in a given measurement, and also may identify an inaccurate measurement.

Data Analysis Students may attempt to address the QOD and their hypothesis from their own data, but eventually a compilation of all data is used to reach final conclusions. Guided inquiry questions during the data analysis phase can help students uncover the intended relationships and concepts. Some application of the newly developed concept is undertaken—possibly as a follow-up laboratory experience Note that for the bp lab, there were no written post-lab questions, but there could have been. Note that the application could be making a prediction and testing it (what is the bp of these three liquids?) or it could be another POGIL laboratory experience (how does the structure/placement of the OH group in an alcohol influence bp?)

The Learning Cycle* Data Acquisition Is there any pattern in the data? Test hypotheses What did you do? Higher level of thinking What did you find? What does it mean? Apply developed concepts Remind participants about the Learning Cycle. They have a copy of this slide in the blue folders. Also, they have been exposed to the Learning Cycle previously – either in previous workshop or in the “1-Day Workshop” session earlier. If necessary, explain the features of the Learning Cycle. Can be useful to use a quick example from a classroom environment (e.g., contrast the introduction of gas laws in a standard way and a POGIL strategy) Don’t say too much about how this compares to the bp experiment because on the next slide you are going to ask them to map the bp experiment onto the learning cycle * Karplus and Thier, A New Look at Elementary School Science, Chicago: Rand McNally (1967); Piaget, Journal of Research in Science Teaching 1964, 2, 176.

Boiling Point Experiment and the Learning Cycle As a group: Identify which components (if any) of the experiment correspond to each phase of the Learning Cycle. Does the boiling point experiment that you worked through follow the Learning Cycle? [2 min] Have them do this as a group to save time. Should be relatively straightforward. The idea is: Exploration: Making predictions and collecting their own data Concept Invention: Analyzing data to see that within a particular type of molecule, bp increases with MW but also that the structure makes a difference at a given MW Application: One (or more) of the proposed extensions of the experiment.

POGIL Laboratory Criteria Refer participants to the written document that is in the “Blue folder”: Required Criteria for POGIL Experiments”. Read through this with document with the participants. You should have a copy of the document that has a more detailed description of what these terms mean; “Detailed Required Criteria…” this can be used to address/clarify questions that participants have about any of the items, or for you to emphasize/explain certain items. The “desirable” criteria are good ones to include, but they do not contribute to “defining” a POGIL laboratory. In particular, student design of experiments is NOT required. These are criteria that together tend to characterize POGIL laboratories. You will find that some of the criteria are not unique to POGIL (e.g., all labs are aiming for the collection of good data). As a collection, they are an ideal, but you may find examples of POGIL labs that doesn’t absolutely include all of them.

Activity 3 Is This a POGIL Experiment? Read through this melting point experiment Identify whether or not each of the required criteria is met (or is likely met) by this experiment. Conclude whether or not this is a POGIL experiment [5 min] Hand out one page description of melting point experiment. Tell them to take 2 minutes to read over (or so) and then discuss as a group each criterion. Don’t spend too much time on any one – if disagreements can’t be resolved move on to next criteria and come back If enough time As groups finish, ask them to generate a QOD for a melting point experiment. Give them about 2 minutes to do this, and then have them report out orally.

POGIL and SWH: Science Writing Heuristic Students write their own question Provides the question Creates student-centered learning environment Required to have student input in the design of experiments Desirable to have student input in the design of experiments Analyze data and discuss as group Uses the SWH lab notebook format Uses the traditional lab notebook format Students as a group experience conceptual negotiation Instructor guides students to appropriate conclusion Emphasis on reflective writing in the notebook Guides students to think about what has been learned (in-lab and post-lab questions) Mention that SWH is another student-centered laboratory approach. Information is available at http://avogadro.chem.iastate.edu/SWH/homepage.htm Workshop attendees may know about SWH and this would be an important slide to highlight the similarities and differences. http://avogadro.chem.iastate.edu/SWH/homepage.htm