Conversion of a Lecture Based Organic Chemistry Course Sequence

Downloaded by PURDUE UNIV on December 4, 2016 | http://pubs.acs.org Publication Date (Web): December 1, 2016 | doi: 10.1021/bk-2016-1228.ch006

Chapter 6

Conversion of a Lecture Based Organic Chemistry Course Sequence to Fully Flipped Classes with Pertinent Observations from Other Flipped Chemistry Courses Vincent Maloney* Chemistry Department, Indiana University Purdue University Fort Wayne, Fort Wayne, Indiana 46805 *E-mail: [email protected]

A largely lecture-based organic chemistry sequence with a significant active learning component for 80 – 100 biology majors and pre-professional students was transformed to a completely flipped classroom format. All traditional lecture was placed online as video recordings for students to view prior to the face-to-face class. Students were asked to complete online homework assignments to demonstrate familiarity with video topics. In the face-to-face class, the entire period was devoted to group problem solving. Otherwise, quizzes, exams, and grading were nearly the same. A student survey was conducted at the end of each semester to examine attitudes towards the new format. The responses showed that the students preferred the flipped classroom. The quiz, exam grades, and performance on the American Chemical Society Form 2004 Organic Chemistry Exam were used for assessment. Scores were compared to the previous two academic years where the course was taught with a more traditional format. No improvement in learning was observed. Observations made during these courses and later in other non-organic flipped courses suggested how learning gains could be achieved. Based on these observations, adjustments were made in later flipped courses where there was improved performance by the students. Recent pedagogical literature has indicated to what extent learning gains could be expected.

© 2016 American Chemical Society Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.

The lessons learned from them can be applied to future organic chemistry courses.


Introduction The following is a chronicle of the conversion of an organic chemistry course sequence that had already incorporated a significant component of active learning to one that completely embraces what is often referred to as a flipped classroom pedagogy (1, 2). The rationale for the change, a description of the structure of the flipped classes, observations of what happened in them and the lessons learned will be provided. Student attitudes were examined and the effect on learning was assessed within the limitations described later. After transforming organic chemistry, the flipped pedagogy was applied to two consecutive sections of a one semester general chemistry survey course. Although the student populations between general and organic chemistry were very different, the flipped general chemistry classes provided insight into what seemed to work and not work in organic chemistry. The subsequent application of formative classroom assessment techniques to the lecture portion of the organic chemistry laboratory also aided in understanding observations from the flipped organic classes. Before describing the course flip, a few qualifications must be stated. As with nanotechnology, the term flipping the classroom has obtained a rather elastic definition. Use of any sort of classroom assessment techniques (CATs) (3, 4), group problem solving, or methods such as Just-in-Time Teaching (5) could justifiably be called to a greater or lesser degree a flipped classroom. In this case, the course flip refers to placing the entire lecture component outside of the face-to-face class in online videos. The entire face-to-face meetings were devoted to group problem solving. The problems chosen were those that had previously been homework and review session questions normally done outside of class. The observations presented here are inherently anecdotal. Although further rigorous studies of the impact of the flipped classroom are required, I hope that the observations and conclusions drawn from the flipped organic chemistry sequence will be an aid to those considering a flipped classroom for their courses. Several conclusions could be drawn from the four flipped courses and the applications of CATs to laboratory lectures. A significant majority of the organic chemistry students preferred the flipped format. Although evidence of learning gains was elusive, there was no evidence of adverse effects on the class as a whole. Observations from the flipped classes and evidence in the literature shed light onto the apparent lack of learning gains and point to where improvements can be achieved. As noted by Freeman et al., if a significant component of active learning is present in a course, then gains may not be observed by adding more (6). That may be the case for the courses reported here. Some improvement was finally seen in the last general chemistry course after making adjustments based on observations from the organic courses. Organic Chemistry I and II (CHM 25500 and CHM 25600) at Indiana U. Purdue U. Fort Wayne (IPFW) were transformed to completely flipped classes. 94 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


The courses were predominantly populated by biology majors and pre-professional students. The courses cover all of the material found in the American Chemical Society (ACS) Form 2004 Organic Chemistry Exam along with additional topics. At IPFW, the organic chemistry laboratory component is provided as a completely separate course sequence (CHM 25400 and CHM 25800) that runs concurrently with the lecture courses. In fall 2013, Organic I had 98 students enrolled while the following spring 88 students were enrolled in Organic II. The face-to-face class periods were conducted in a lecture hall holding 126 students. The room was tiered and seating consisted of rows of fixed tables and seats. The classroom was not designed for peer learning. Nonetheless, the students managed. IPFW was at the time a regional campus of the Indiana-Purdue system with an enrollment of 12,840 students. In 2013, the average SAT score of beginning students was 1478. The university conferred mostly B.A. and B.S. degrees with a few M.S. programs.

Rationale for the Course Flip The main impetus for introducing active learning was the mounting evidence that it improves student learning and enhances their performance. Recently, Freeman et al. confirmed such gains with a meta-analysis of 225 studies of active learning versus traditional lecture (5). Performance on exams, concept inventories and course failure rates were compared. In their conclusion that active learning should be preferred over traditional lecture, the authors questioned the use of solely traditional lecture in the classroom even as a control in research. It should be noted that courses “with at least some active learning” (6) were compared to traditional lectures where presumably there was no active learning of any sort. It is difficult to read such statements and continue to rely on the traditional lecture. Active learning has been used in IPFW organic chemistry courses since 2000 based on the peer instruction methods developed by Eric Mazur (7). Although the meta-analysis of Freeman et al. was not available when the courses were transformed, compelling evidence from Hake (8) and Deslauriers (9) was. These reports show that students in physics courses with active learning (referred to as interactive engagement) scored higher on force concept inventories than students in traditional lectures (8). The performance of the highest scoring traditional lecture classes was comparable to that of the worst performing active learning classes. The question then became whether the amount of active learning should be increased so that it filled the entire face-to-face class meetings for the organic chemistry courses described here. Although the primary rationale for attempting an alternative pedagogical method is improved learning, there are other reasons to do so. Like many other institutions, retention of students in classes and at the university has become an issue of concern at IPFW. Improving graduation rates has also become a consideration. It is imperative to avoid loss of rigor while improving retention. Learning activities that increase interactions between faculty and students and among students tend to increase retention (10). Active learning that involves peer instruction can possibly achieve these ends and enhance learning. The flipped 95 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


pedagogy extends these activities to the entire face-to-face class meeting and potentially maximizes these interactions. The media hype surrounding massive open online courses (MOOCs) (11) may have passed, but they and their providers such as Coursera, Edx, and Udacity have not. Offering inexpensive courses based on the MOOC format can be imagined. It could be argued that such courses would not be as effective as one where an expert in the field is fully engaged with the course and students. However, could they be good enough so that the cost of an expensive face-to-face course could not be justified for students of low and moderate incomes? Whether true or not, it does pose the question of what is the most effective way to spend precious time in the face-to-face classroom. The evidence indicates that a live lecture with homework and problem solving done outside of class is not as effective as recorded lectures (or other forms of course content) viewed before class and problem solving in the form of active learning done in the classroom. Recorded lectures have existed practically since the technology has made it possible, but current technology has improved access. Cell phones and tablet computers make it possible for students to download course content almost anywhere and anytime. With learning management systems, all course materials such as the text, notes, other supplemental materials, and the lectures themselves can be accessed with a portable device. It has always been possible to flip the course by requiring students to come to class prepared by reading the text and then doing problem solving. Now it is possible to do the same, but still provide lectures in the form of online videos. The current state of technology has made it easier to flip the course. The potential of improving student learning was the primary motive for transforming the organic courses. Retention, the challenge of MOOCs, and the ease of student access to course materials were all important secondary motivations.

Structure of the Course Flip To put this implementation of the flipped course in perspective, it will be necessary to describe the organic chemistry courses at IPFW before fall 2013. A traditional lecture course may be considered to consist of the following sequence of events before, during, and after class. The students are assigned a reading from the text to complete before the class meeting. In class, the instructor lectures on the topics and assigns homework questions afterwards. Students alone or in groups work on the homework and may ask the instructor questions about the material before the next meeting. If some type of CAT is not used during lecture, student problems with the material are not recognized until a quiz or exam. In practice many faculty conduct classes that are not just traditional lecture. They incorporate active learning to greater or lesser degrees. Active learning was used in the organic sequence at IPFW prior to fall 2013. 96 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


The impact of the flipped organic sequence was examined by comparing it to the same sequence over the previous 2 academic years. The course topics were essentially the same. The final exam for the 2nd semester courses was the ACS Form 2004 Organic Chemistry Exam. The class sizes were similar. In each course, the class met three times a week for 50 min. For the two years prior to the complete flip, the course was not a simple traditional lecture. Students were given assigned readings. In the face-to-face class, the same topics were described in a lecture format. The lecture notes were provided as PowerPoint files for the students to print beforehand. In nearly each face-to-face meeting, questions were posed for all students to answer to assess their understanding of concepts just presented. A classroom response system (clickers) was used so that all students would answer. Best practices suggested for clicker use were employed (12). With each question, the students were given time to discuss their answers in informal groups before entering a response. On average, 3 questions were posed each day. The number and length of the questions varied with the material. All class meetings were recorded with a lecture capture program for subsequent review by the students online. Beyond that, optional review sessions were offered to the students twice weekly. IPFW doesn’t provide for recitation sections. Although rarely more than half the class attended these optional review sessions, significant numbers of students did show up regularly. These sessions involved an hour of group problem solving. Online homework was assigned after the lecture. Besides the extensive use of CATs, the flipped pedagogy had been piloted in both courses with nomenclature topics. At appropriate points, students were asked to watch lecture capture videos covering nomenclature. Upon arrival, they took a short quiz to demonstrate that they had learned the basics from the videos. Once the quizzes were handed in, more challenging nomenclature problems were covered as group problem solving clicker questions. These pilots of the flipped pedagogy were positive indicators that the flipping could be extended to the entire course. Beginning in fall 2013, the sequence was completely flipped. All lecture content was placed online as videos to be viewed outside of the class. A substantial portion of the problems covered in the homework and review sessions were moved into the class periods for group problem solving. In preparation for the courses, videos of the lectures were recorded. These videos were created with the same lecture capture program which recorded both the instructor and whatever was on the computer screen such as PowerPoint slides. Instead of 50 minute lectures, nearly all of the videos were less than 20 minutes. Some were as short as 1.5 min. The length of the video was dictated by the time it took to explain a single topic or concept. This choice was based on the method known as chunking (13). Reducing the material into manageable pieces helps students process the material. The lecture content was otherwise largely the same as those given over the previous two years. The same PowerPoint notes were used. They were merely broken up into smaller files to match the online video content. For the entire sequence, 295 videos were prepared: 130 for the Organic I semester and 165 for Organic II. Despite the difference in number, approximately 17 h of lecture was recorded for each semester. This low total was surprising. With each class having a length of 50 minutes, 17 h corresponds to 20.4 classes. Each semester is 15 weeks long with 3 classes per week giving a total of 45 classes. 97 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


Subtracting 5 class meetings for exams and quizzes, there should have been 40 classes. Yet the videos amounted to only 20.4. Although some time would have been taken up with announcements and student questions, it wouldn’t account for 23.6 classes. The bulk of this missing class time time had been spent in group problem solving instead of lecture. The organic courses prior to fall 2013 already involved a significant amount of active learning rather than lecture. An important component to flipping the course was to prepare the students for the new format. A complete description of the format, student expectations, and rationale was placed in the syllabus. In particular, it was stated that there was a significant amount of evidence supporting the use of active learning and that it should benefit them in increased learning and improved grades. The first class began with a review of general chemistry. The students were asked clicker questions to determine what they had retained. They were expected to watch videos after that. For a typical class, the students were asked to watch a number of videos and read the corresponding material in the text. The assigned videos corresponded to the topics planned for the upcoming class. The PowerPoint slides used in each video were made available to the students online for subsequent study. To ensure that they had prepared, the students were asked to complete an online homework assignment before class. These questions were relatively simple and used to assess their readiness for more complex problems. For Organic I, 162 homework questions were written while 98 were prepared for Organic II. These question types were those commonly available in learning management systems rather than chemistry-specific questions that involve students drawing structures. Commercial online homework products were not found to be suitable since the questions needed to be directed at specific planned activities in the face-to-face meeting. The software and site for the recorded videos does allow the instructor to view whether students had accessed the videos and how many times. A range of activity was observed. Some accessed the videos numerous times; some didn’t view the videos at all. During class, the entire time was devoted to group problem solving using questions modified from the text and review sessions from previous years. Initially a review of the assigned topics was provided at the beginning of that day before the planned CATs. It rapidly became apparent that the students didn’t need or want it. They wanted to get to answering questions and solving problems. Many of the questions were short and it was possible to work through 10 to 12 clicker questions per class meeting. The time spent per question varied with their content and type. Ruder has provided a useful resource for clicker questions to use in organic (14). The individual questions used for Organic I and Organic II at IPFW can be accessed at http://organicers.org (15). Typically, the questions were displayed on a PowerPoint slide to the students. After students took time to briefly discuss the problem, they entered their answers using their clickers. Multiple choice, numerical, and text question formats were used. The entire PowerPoint file without answers was provided online at least one day before class. The students were allowed to use any resource such as the text, notes and any device to access information. Some students printed out the questions while others accessed them with their cellphones and tablets. 98 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


Although most questions were answered quickly, more in depth problems were given. For example, for spectroscopy, the students were given the molecular formula and IR, 1H NMR, and 13C NMR spectra for a compound. They were asked to draw the structure for the compound. The correct structure and the four most common incorrect structures were placed on the board. The students then voted on the one they thought was correct. Such polling could be used after students are asked to draw transition states, conformations, and reactive intermediates in a mechanism. For synthesis, the students were given a table of 10 to 15 reagents. Each reagent was given a number. They were then asked to propose a synthesis for a compound from a given starting material. Once they had finished, they entered the correct order of reagents in the synthesis as a sequence of numbers. Such problems could take 10 to 20 minutes of class time. Flipped courses were designed to be time neutral. The time that the students were expected to spend on a traditional course or a flipped course per week was to be the same. The amount of time that should have been spent on attending lectures, reading the text, completing homework, studying notes, etc. was estimated for the previous courses. Then the flipped class activities were designed so that the same amount of time would be spent in the new course format. In effect the time and location of course activities were shifted and not increased or decreased for the flipped courses. The students were expected to spend 12 h on organic chemistry per week: 3 in the classroom and 9 outside. As in the past, it appeared that some did more and some less. Grading for the organic sequence was kept largely the same. The same schedule of exams and quizzes was used. The pace of the courses were similar so that much of the same material was covered on each exam. For all three years the ACS Form 2004 Organic Chemistry Exam was used as the final for the 2nd semester. The grading between the flipped and previous courses was nearly the same. See Tables 1 and 2 which outline the grading for Organic 1 and 2 courses. They show the total number of points a student could achieve in a semester and what each assessment was worth. For each course, two 50 min. exams worth 100 pt. (200 pt. total) and four 25 pt. quizzes (100 pt. total) counted towards their final grade. The students actually took three exams and five quizzes with the lowest grade of each being dropped. The online homework was worth 50 points whether it was post class before the transformation or pre-class after the complete flip. Two assessments, clicker questions and nomenclature quizzes require further explanation. In all three years, students were assigned points for participating in group problem solving and individually answering with their clickers. Points were only assigned for answering and not for being correct. One concern that could be raised is that students were potentially given points for random answers without any attempt to actually work the problems. Although there was no apparent evidence of this behavior, the more plausible scenario is that students would answer whatever the “A” student nearby chose. Assigning points for correct answers would not have prevented students from answering in this manner. With the policy, group problem solving became formative assessments for the students and instructor where misconceptions could be addressed without the pressure of these activities affecting their grades adversely. 99 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.

Table 1. Grading for the Organic Chemistry I Courses Year


a

Exams

Quizzes

Nomenclature Quizzes

2013 (flipped)

100a

0

200

150

50

50

550

2012

100

25

200

150

25

50

550

2011

100

25

200

150

25

50

550

Final Exam

Clicker

Homework

Total

All numbers besides those for years represent points towards the course total.

Table 2. Grading for the Organic Chemistry II Courses Year

a

Exams

Quizzes

Nomenclature Quizzes

2014 (flipped)

100a

0

200

200

50

50

600

2013

100

25

200

200

25

50

600

2012

100

25

200

200

25

50

600

Final Exam

Clicker

Homework

Total

All numbers besides those for years represent points towards the course total.

The nomenclature quizzes previously mentioned for the courses prior to fall 2013 were worth a total of 25 points. Upon transforming the course, it was more consistent to treat the nomenclature topics in the same manner as the rest of the course. Also, it was deemed better to use the class time for more active learning instead of short quizzes. The nomenclature quizzes were no longer given and 25 more points were added to clicker total. It may seem that these points should have been added to the homework total. Instead they were added to the clicker total since the students were doing significantly more group work. Assigning a significant amount of points to these activities helps to convince students of their importance. Somewhat surprisingly, the nomenclature plus clicker point total scores were comparable to the clicker point score of the flipped classes.

Assessment Student attitudes about the flipped courses were assessed by conducting surveys in the penultimate class of the semester. The survey consisted of 22 statements using a Likert scale where students could respond from 1 strongly disagree to 5 strongly agree. Of the 22 questions, 7 referred to how well the software and technology worked for the students. Overall the majority of students had positive attitudes about the course flip. The majorities were larger in Organic 100 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


I than Organic II. A small percentage of students did strongly disagree. A majority of students agreed with a statement suggesting that they could be building the type of relationships that aid in retention in a course and at the institution (10). Since the primary motivation of transforming the organic sequence to the flipped format was improved student learning, the grades within the course and the score on the ACS exam were compared. Comparing quiz, exam, and course total scores and grade distributions is problematic. Efforts were made to use the same or sufficiently similar course materials, exams, quizzes, etc. Unfortunately, ensuring that they are sufficiently alike is difficult. Some decisions were made to make changes to accommodate the flip or improve an observed deficiency. For example, a switch from commercial online homework to one specifically designed for the transformed courses was made. Since exams and quizzes from the previous year were always made available to the students, they could not be reused. Efforts were made to make them similar, but equivalency between exams and quizzes in different years could not be ensured. Despite these complicating factors, it was hoped that some improvement in performance would be observed after the complete flip. A better instrument for assessment was the ACS organic exam. It was the same exam for all three years and given under similar conditions. In examining the overall course and the ACS exam scores, there was not a significant increase or decrease in performance over the 2 semester sequence. Given the possible variability affecting scores, it could be said that the three groups performed comparably. In the ACS exam the flipped class mean score fell between the means of the 2013 and 2012 classes. Although it was important that student performance did not decline, it was discouraging to observe no consistent or reliable indication of improved learning. It could be said that since there was no decrease in performance and the students preferred the flipped classes, this outcome would be sufficient reason to continue with the new format. This result was unsatisfactory however considering the main goal. It remained then to examine why improvement wasn’t observed. Although the evidence supports active learning, there certainly would be limits to its benefits. There are two aspects of this particular course flip that might come up against potential limits. Freeman et al. did report that the impact does decrease with increasing class size (6). Active learning had the largest effect for classes with less than 50 students. However medium (50 – 110) and large classes (>110) still benefit from active learning, just less so. It was also reported in their analysis that they were not able to determine what relationship between the intensity of active learning and student performance existed. Recently Jensen et al. reported that student achievement in and student attitudes towards a course with some active learning versus a fully flipped classroom were similar (16). It is then not clear to what extent more is better. Given the uncontrolled variables, the somewhat diminished impact of active learning as class size increases, and the high degree to which active learning was already incorporated in previous years, it may not be surprising that in the first attempt at a completely flipped classroom at IPFW, significant gains were not observed. Observations made during the transformed organic courses, two subsequent flipped general chemistry courses and the addition of CATs to the lecture portion of an organic laboratory course provide insight to where adjustments could be made to enhance learning. 101 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


Subsequent Adjustments to the Course Flip Several potential areas for improvement were noted for the organic courses. First the nature and quality of the pre-class homework needed to be reconsidered. Gross et al. have reported that this is an important consideration in how the flipped classroom can improve student performance (17). Although it may be valuable to evaluate whether students have grasped the most basic information, more challenging questions indicating what could be expected in class should be included. It also became apparent that post-class homework that reinforced the activities in the face-to-face meetings should be added. Since not all aspects of a topic could be covered in class through active learning, some follow up questions that stretched the students also seemed worthwhile. These changes were subsequently incorporated into one semester survey courses in general chemistry. Questions of this type will be developed for future organic chemistry classes. The second adjustment involved the ordering of the concepts chosen and complexity of the questions. Initially, questions were asked in a semi random order similar to what is done in an exam or quiz. Realizing that this approach did not seem to have the expected impact, the choice and order of questions were modified. The in class questions were initially simple, but each succeeding question involved concepts that built upon one another and increased in complexity until students had reached the course goal for a topic. The recognition that this order would be preferable developed over time and was not fully implemented for the organic chemistry courses. When it was employed, it was relatively easy to follow the progression of the video lectures and narrative in the text. Table 3 gives an example of a progression of question topics on electrophilic addition. For their first question, the students were asked to predict the product for the reaction of HX with a symmetrical alkene. For the second they would be asked about the mechanism and so on. In the text used for the course, electrophilic addition was split between 2 chapters. The topics in Table 3 represent those in the first chapter. It could be covered in as little as two 50 min. class periods. Although changing the homework and in class questions was valuable, two other problems were recognized and addressing them had a greater impact on potentially improving the courses. With the report that class size affected the efficacy of active learning, consideration was given to how to mitigate the effects of the large class size (6). The other problem was that more interactions between the instructor and the students was desired in the classroom. Too much time was spent by the instructor running the clicker software and placing explanations on the board and not enough time talking with students about their answers. Due to staffing needs within the IPFW chemistry department, I was scheduled to teach general chemistry. Consequently, in fall 2014 and spring 2015, CHM 11100 general chemistry was flipped. Although many aspects of teaching general chemistry and organic chemistry are different, there are some are commonalities. Those observations and adjustments that are applicable to the flipped organic chemistry courses will be presented here. CHM 11100 is a survey course that fulfills a general education requirement for the state of Indiana. For the fall, there were 96 students while in the spring semester, the population was 76. Both semesters the students consisted of dental hygiene, engineering technology, 102 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


elementary education majors. The instructor had not taught this course previously and had not taught general chemistry since 1993. There was no equivalent course for a comparison for the flipped format. From the fall to the spring, two changes were made. The instructor took steps to spend more time with the students. On most questions, the instructor spoke with two or more students (or groups) and discussed answers that were incorrect. A supplemental instructor (SI) was attached to the course. Undergraduate students with high GPA’s who have performed well in the same course or higher can become supplemental instructors. Normally they attend each class and lead two review sessions a week. For this course, the SI was asked to engage with the students in the same manner as the instructor. Increased engagement with the students mitigated the class size. Simply, two people could reach more students than one. Improvement was found from the fall to the spring general chemistry courses. All quiz and exam averages were higher in the spring to a greater or lesser degree. Although the rate of D grades, F grades, and course withdrawals was slightly higher in the spring, among the A, B, and C grades, there was a higher percentage of A’s and B’ relative to C grades. Unfortunately there is some contradictory evidence and complicating factors that make such a conclusion difficult to verify. Both the clicker and homework grades were lower in the spring semester. Clicker grades are based on the number of responses and students who stop attending will have very low scores. These are counted into the average and will skew the overall average lower. In the fall, a commercial online homework product was used while in the spring the online homework was developed by the instructor. The latter had more fill in the blank and less multiple choice which may have been more challenging for the students. For the same reasons as the clicker average, a higher percentage of students who stopped attending would make the homework average appear lower. The SI did conduct review sessions which were not available to the fall students. The attendance was low, but those who did attend should have benefited in their quiz, exam, and final grades. The instructor taught two sections of lab to the students unlike the fall. More time spent this way with the students would have certainly improved engagement. Finally the observed differences in the grades were not large and could be attributed to unidentified factors and normal variability. There was another potential problem to consider. Perhaps the active learning introduced was conducted in a completely ineffective manner. In fall 2015 CATs were introduced into the lecture portion of the organic laboratory course to some topics where it hadn’t been done previously. It was observed that the quiz averages were higher than they had been in the previous year. Apparently active learning was implemented properly and improvements could be observed. For those who are considering flipping their class, there are some final aspects to contemplate. Compared to a traditional lecture class, a flipped class solely devoted to peer to peer learning will certainly appear chaotic. The instructor should be comfortable with the prospect. In all of the flipped classes, informal groups were used for problem solving. It has been suggested that formal groups are preferable (18). Finally in the author’s experience, placing all lectures online provided more flexibility in the classroom. Easier topics can be completely left to the video lectures and homework. More difficult topics can be addressed as needed 103 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.

in class. Student answers to questions readily indicate where more time needs to spent. It also provided more time to address specific student difficulties.

Table 3. An Example of Increasing the Complexity of Topics for Group Problem Solving Questions in the Flipped Classroom for Electrophilic Addition to Alkenes


Question Topics and Their Order 1. Product of the addition of HX to a symmetrical alkene

11. Carbocation stability: hyperconjugation, polarizability and alkyl groups

2. Mechanism of addition

12. Carbocation stability: Resonance effects and addition to vinyl halides and vinyl ethers

3. HOMO and LUMO in each step of mechanism

13. Stereochemistry of addition: Formation of both enantiomers

4. Acid catalyzed hydration of a symmetrical alkene

14. Carbocationic polymerization

5. Mechanism of acid catalyzed hydration

15. Carbocationic polymerization: Lewis acids and initiation

6. Role of the acid catalyst

16. Carbocationic polymerization: Suitable alkenes

7. Addition of HX to an unsymmetrical alkene: 2-methylpropene

17. Carbocation rearrangements and addition

8. Regiochemistry and Markovnikov’s rule

18. Carbocation rearrangements: Preference for more stable carbocation

9. Carbocation stability

19. Carbocation rearrangements: ring expansion and contraction

10. Carbocation stability: Inductive effects

Conclusion Based on the 2013-2014 course sequence, it can be said at the very least that flipping organic chemistry courses can be achieved without adverse effects to performance while increasing student satisfaction with their experience. Jensen et al. have indicated that a full flip may not be necessary to achieve learning gains (16). Their report may explain the comparable scores between the organic classes with a significant amount of active learning and the fully flipped courses. Beyond that there are indications that proper choice of pre- and post-class activities, appropriate question order and complexity, increased levels of engagement by the instructor and teaching assistant(s) can potentially lead to improvements in learning. 104 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.

Freeman et al. were strong in their statements about the value of active learning over traditional lecture (6). It is clear that a significant component of active learning should be present in any class. A complete flip may not be necessary, but to those who prefer the classroom environment and engagement with students that it provides, it will work.

Acknowledgments


The author would like to thank Gail Rathbun, Director of the Center for the Enhancement of Learning and Teaching and the Department of Chemistry at IPFW for their support.

References Bergmann, J.; Sams, A. Flip Your Classroom: Reach Every Student in Every Class Every Day; International Society for Technology in Education: Washington, DC, 2012. 2. Morgan, R. K.; Mitchell, N. G.; Chapman, N. To Flip or Not to Flip; Is That My Only Choice. In It Works for Me, Flipping the Classroom: Shared Tips for Effective Teaching; Blythe, H., Sweet C., Carpenter, R., Eds.; New Forums Press: Stillwater, OK, 2015; p 2. 3. D’Angelo, T.; Cross, K. P. Classroom Assessment Techniques: A Handbook for College Teachers; Jossey-Bass: San Francisco, CA, 1993. 4. Nilson, L. B. Teaching at Its Best: A Research-Based Resource for College Instructors, 3rd ed.; Jossey-Bass: San Francisco, CA, 2010; pp 273−280. 5. Novak, G. M.; Gavrin, A.; Christian, W.; Patterson, E. Just-in-Time Teaching : Blending Active Learning with Web Technology; Prentice Hall: Upper Saddle River, NJ, 1999. 6. Freeman, S.; Eddy, S. L.; McDonough, M.; Smith, M. K.; Okoroafor, N.; Jordt, H.; Wenderoth, M. P. Active Learning Increases Student Performance in Science, Engineering, and Mathematics. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8410–8415. 7. Mazur, E. Peer Instruction: A User’s Manual; Prentice Hall: Upper Saddle River, NJ, 1997. 8. Hake, R. R. Interactive Engagement versus Traditional Methods: A SixThousand-Student Survey of Mechanics Test Data for Introductory Physics Courses. Am. J. Phys. 1998, 66, 64–74. 9. Deslauriers, L.; Schelew, E.; Wieman, C. Improved Learning in a LargeEnrollment Physics Class. Science 2011, 332, 862–864. 10. Smith, K. A.; Sheppard, S. R.; Johnson, D. W.; Johnson, R. T. Pedagogies of Engagement: Classroom Based Practices. J. Eng. Educ. 2005, 94, 87–101. 11. Leontyev, A.; Baranov, D. Massive Open Online Courses in Chemistry: A Comparative Overview of Platforms and Features. J. Chem. Educ. 2013, 90, 1533–1539. 12. Bruff, D. Teaching with Classroom Response Systems: Creating Active Learning Environments; Jossey-Bass: San Francisco, CA, 2009. 1.

105 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.


13. Nilson, L. B. Teaching at Its Best: A Research-Based Resource for College Instructors, 3rd ed.; Jossey-Bass: San Francisco, CA, 2010; p 8. 14. Ruder, S. M. Clickers in Action: Active Learning in Organic Chemistry; W.W. Norton and Company: New York, NY, 2013. 15. Organic Education Resources: A cCWCS Community of Scholars. http:// www.organicers.org (accessed Jan. 18, 2016). 16. Jensen, L. J.; Kummer, T. A.; Gody, P. D. d. M. Improvements from a Flipped Classroom May Simply Be the Fruits of Active Learning. CBE Life Sci. Educ. 2015, 14, ar5. 17. Gross, D.; Pietri, E. S.; Anderson, G.; Moyano-Camihort, K.; Graham, M. J. Increased PreClass Preparation Underlies Student Outcome Improvement in the Flipped Classroom. CBE Life Sci. Educ. 2015, 14, ar36. 18. Johnson, D. W.; Johnson, R. T.; Smith, K. A. Cooperative learning Returns to College: What Evidence is There That It Works? Change 1998 (July/ August), 27–35.

106 Muzyka and Luker; The Flipped Classroom Volume 2: Results from Practice ACS Symposium Series; American Chemical Society: Washington, DC, 2016.

Conversion of a Lecture Based Organic Chemistry Course Sequence

Recommend Documents