After reading about flipped classrooms and attending an NSF-sponsored cCWCS workshop (Chemistry Collaborations, Workshops & Communities of Scholars) June 20-23 2016, I decided to try out flipping my organic chemistry lecture. My class meets for lecture every Monday, Wednesday, and Friday for 50 minutes. I decided to try out flipping my organic class on Fridays only as an experiment during the fall semester of 2016. First I had to become comfortable with recording my lectures. After investigating several software programs, I settled on the use of Debut Video Capture. Several other software programs were just as good, but Debut was simple to use and easily recorded my computer screen and my voice very well. An additional incentive was a free 3-month trial followed by a one-time fee of $19.99 for use of the software. I’ve used this software for two years now and find no reason to switch. I show PowerPoint slides on half of the screen and Paint software on the other side. With the Paint software, I can draw anything necessary, or I can pre-copy and paste items before recording. These recorded lectures are posted a week in advance by downloading them onto YouTube and providing the URL to my students. Sometimes I either collect a copy of their notes or quiz them to provide incentive for watching the online videos. During class on Fridays, we work on problems related to the online lecture. I have introduced a variety of activities into Fridays including worksheets, mini-quizzes, Kahoot online quizzes, old exam reviews, individual problems that they answer and explain on the whiteboard, etc...  One of my favorite activities involves predicting pka values. I bring in individual slips of paper with one organic structure on each. Students are given a slip of paper with an organic acid or base, then they have to compare to their neighbor’s structure and rank them based on relative acidity. Then each group of two students compared their ranking to another group of two students. We then have time to review the results and talk about inherent problems with predicting relative pka values.   Friday lectures are now fun! They are energetic, real active learning takes place, students sharing their ideas is the focus, not the professor. I can use Friday’s for pre- and post-exam reviews, for class-cancellation make-ups, for a more detailed review of complex topics, etc...  I sometimes bring in a bag of cheap gifts for students to compete for. I truly believe I am a better teacher because of the flipped classroom concept. ... View more

Macmillan Learning is proud to announce that The Flipped Learning Global Initiative has named Introductory Chemistry author Kevin Revell one of the top 40 Flipped Learning educators worldwide. The list, compiled annually by the FLGI executive committee, names the top 100 K-12 educators from around the world who are identified as driving forces of flipped classroom adoptions. This year, the initiative broadened their recognition to include the top 40 Flipped Learning leaders in higher education. FLGI’s Chief Academic Officer, Jon Bergmann, stated, "The 2017 FLGI Flipped Learning Leaders lists includes some of the most experienced, innovative and proactive education and training professionals in the world. These are the people driving Flipped Learning forward in thought and action and demonstrating what is possible when Flipped Learning is done well." Congratulations, Kevin! ... View more

Instructors (at all levels) have devised means of content transfer which do not involve the primary course texts as a response to student's seeming unwillingness to tackle, or inability to comprehend, the text. Over the years, many instructors developed a detailed set of class notes, presentation slides, videos, etc. that cover all of the important topics in the course. My teaching philosophy was very similar. Early in my teaching career, I required readings, but when I realized that students were consistently not comprehending, I didn't know where or how to deal with the problem, so I decided to work around the text, essentially reducing the 1000 page text into a collection of end of chapter problems. I didn't understand the reason why reading was so difficult nor did I have the tools to teach reading in my classroom. Moreover, I didn't think it even appropriate to be teaching reading in college level chemistry and math courses – shouldn't the students have already learned how to read? This semester I was introduced to a framework – not a program - through which reading is given high priority in the classroom and the instructor is given concrete tools to help students become proficient discipline readers. The framework is called Reading Apprenticeship (RA) [1]. In RA, the instructor is the content expert, who is capable of reading discipline texts. The instructor's role in RA is to provide a safe, collaborative environment in which students can be apprenticed to become proficient readers. In this framework the instructor demonstrates all of the techniques they use when reading. RA gives instructors concrete exercises and terms by which they can describe their reading and thought processes. The metacognitive discussion that arises through each of the dimensions listed below helps students develop into their thought processes to become readers. RA recognizes that reading is a very involved process that involves several distinct dimensions. The dimensions of RA include (link to graphic😞 Social - Students help each other comprehend texts by sharing and observing each other's reading processes Personal - Students develop their identity as a reader Cognitive - Students learn problem solving strategies applicable to reading comprehension Knowledge-building - Gaining knowledge about the discipline through reading, linking with previous knowledge I have been incorporating RA practices into my chemistry and math classes this semester and am very pleased with the results. Students are able to break down complex sections of the textbook in preparation for class. Moreover, students are able to apply RA concepts to problem solving because the first step in problem solving is being able comprehend the problem. As the semester progresses, I will write up examples of the RA strategies that I am employing in my courses and discuss how students responded. References: [1] Schoenbach, Ruth, Cynthia Greenleaf, and Lynn Murphy. Reading for Understanding: How Reading Apprenticeship Improves Disciplinary Learning in Secondary and College Classrooms. San Francisco: Jossey-Bass, 2012. ... View more

Last fall, I implemented a set of benchmark quizzes in my organic chemistry classes.  These quizzes arose from a simple question:  “What should every student who passes my class be able to do?”  Adapting the approach of Joshua Ring, the quizzes were pass-fail, with no partial credit.  Students had more than one attempt to pass the quizzes, but they had to get the quiz completely correct in order to pass.  Further, I tethered the quizzes to students’ homework grades:  In order to receive credit for homework, students had to pass 5 of the 6 benchmarks by the end of the semester. Not everything went as planned.  My benchmarks were compressed toward the end of the semester, leading me to trim the number of quizzes and removing the restriction on the homework grade.  Nonetheless, the results were remarkable:  Rather than limping through exams with partial credit and moving on to other topics, the multi-attempt, pass-fail approach drove students to analyze their knowledge gaps and hone their understanding.  After two or three failed attempts, students often made their way to my office to figure out what they did wrong.  It clearly made them stronger. Quantitatively, I was able to compare my class to the previous two semesters, using the ACS standardized exam.  The only major pedagogical change was the introduction of the benchmarks.  Here are the exciting results: Semester Students Average Percentile Fall 2015 58 56 Spring 2016 40 45 Fall 2017 46 73 I don’t think the Benchmark quizzes can be exclusively credited with these outcomes.  Our fall classes are usually stronger, and this was an exceptional bunch.  However, they definitely contributed.  I was especially interested to see the effect on those students at the bottom of the class, who often have the most pronounced knowledge gaps.  Here is the change limited to those students who finished in the bottom quartile of the class on the ACS exams: Semester Students Average Percentile Fall 2015 15 17 Spring 2016 10 11 Fall 2017 12 23 This semester, I've moved out of the organic sequence and into Introductory Chemistry.  I'm teaching large daytime and evening sections, and using an adapted benchmark scheme for both.  More to come about this in an upcoming article. ... View more

What should every student who passes my organic class be able to do? Joshua Ring is an associate professor of organic chemistry at Lenoir-Rhyne University.  This past summer, I had the opportunity to hear Joshua give a talk at BCCE.  He posed this question, and offered an innovative solution, recently featured in C&E News.   In essence, Joshua flips his class, then uses a series of benchmark quizzes built around the learning objectives.  The quizzes are pass-fail.  He gives no partial credit.  However, students have multiple attempts to demonstrate mastery.   In his class, there are about 7 essential benchmarks that students must pass in order to pass.  There are 14 additional benchmarks – the number of these that the student is able to pass determines the final grade. The Modification Although the class structure at my school is much different than at Lenoir-Rhyne, I was intrigued.  I therefore designed a modified benchmark system for my class.  We began with six benchmarks: Structure – Draw Lewis structures with correct formal charge and electron counts; identify electronic & molecular geometries & hybridization Nomenclature – Correctly name key molecules, including alkanes/alkenes/alkynes Function – identify acidic and basic sites, nucleophiles, electrophiles S N 1, S N 2, E1, E2 - Show complete arrow-pushing mechanisms for these four fundamental processes. Reactions of Alkenes - Show products from addition reactions to alkenes. Spectroscopy - Identify major features from NMR/IR/MS The benchmarks were pass-fail, but students had more than one attempt to take them.   The class also included an online homework grade.  However, in order to “unlock” their homework grade, they had to pass five of the six benchmarks. Implementation  Here is one version of the first benchmark quiz: Students had to be essentially 100% right to pass.  The first time, only about 44% passed.  The next time it was offered, another 30% passed.  Eventually, nearly everyone in the class passed the exam. The thing I liked about this was that it stressed to students the importance of learning the fundamentals.   And it seemed to pay off as the class wore on – I saw fewer problems with identifying electronic geometry or goofy formal charges on mechanism questions.  Unfortunately, I could not fully implement the benchmark scheme.  Because of the coverage of our text, too many of my benchmarks landed later in the semester, and, pressed for time, I was forced to cut the benchmark quizzes short, and also to remove the tether to the homework grade.  Despite the fizzle at the end, I was pleased with this first attempt.  I feel that my students are better prepared heading into organic 2 than they have been in the past.  The pass-fail approach drove students to practice the material until they got it down.  Outlook I am not teaching organic next semester, and so won’t have an immediate opportunity to improve on the approach with that course.  However, I plan to institute benchmarks for introductory chemistry.  I am planning on 12-14 benchmarks (essentially one per chapter), closely tied to the chapter learning objectives.  Students will take benchmarks at the beginning of lab each week.  I’m excited to see how it goes! ... View more

[originally posted spring 2015] We introduce nuclear magnetic resonance topics in the second semester of organic chemistry lab. During the first two weeks of lab, we spend time lecturing on proton and carbon NMR theory and spectral interpretation with some built-in time for students to work on practice problems, learn NMR processing software (ACD/Labs NMR Processor), and become familiar with our NMR instrument. In the past, I lectured for a little over an hour using PowerPoint, then had students work on several problem sets. This approach was less than ideal. Students got very restless over the lecture portion of the lab period and would later tell me that it felt like too much information coming too fast. Further, because I spent so much time lecturing, students didn’t have enough time to work through the problems and ask questions during the lab period. I began to look for a way to make the lab less overwhelming to students, more interactive and engaging, and incorporate more time for problem solving. I have been producing video lectures and flipping some topics in lecture for over five years now, with some success. Flipping a laboratory topic such as NMR seemed more and more appealing, so I decided to try it out this year. I recorded my usual PowerPoint presentation, but instead of one hour-long video for students to watch, I broke up the lecture into five shorter videos (approximately 10-12 minutes each) focusing on NMR theory, chemical shifts, electronic shielding, integration, and spin-spin splitting. Students were given a week before the lab period to watch the videos and be ready to work problems. They were able to print the PowerPoint slides and bring them to lab to refer to them while working on the assignments. Students, while working in small groups, were given a graded multiple choice assessment to complete by the end of the period. This assessment was used to test the basic knowledge covered in the videos. Students were also given take-home assignments of spectral interpretation problems to be turned in the following week. One major difference I noticed was that students needed much more time to complete the multiple choice assessment than in the past, when I conducted the lecture at the beginning of lab. This could be a consequence of students not watching the videos (though nearly all students claimed to have watched them) or not having the information “fresh” on their minds. So next semester I plan to use this multiple choice assessment as a pre-lab activity instead. Overall, flipping NMR worked out well for me because of the extra time I was able to spend with each small group of students, answering questions and discussing common errors/pitfalls. It was particularly nice in lab where the total number of students is much smaller than in a lecture class. The added benefit to students was that they were able to start and progress further through the take-home assignments during lab than in the past. As a result, students scored higher on the take home assignments, presumably because they were able to ask more questions and get extra help from me and from each other. The flipped approach seems to have helped me achieve my goals of making NMR more engaging and approachable to students. It was also enormously more fun than the traditional “lecture – then problems” approach used in the past. One additional consideration in favor of flipping NMR is that the recorded videos can be made available to any lab instructor for use in their lab sections. This can benefit those lab instructors who are comfortable guiding students through problem-solving activities, but who might not be as experienced or comfortable with lecturing on the material. Moreover, flipping NMR (or other laboratory topics for that matter) could be very useful for coordination of content across the multiple lab sections. ... View more

One of the challenges of teaching organic is getting students to analyze chemical reactions based on the entire chemical system.  Let me give three examples, and share a technique that I’ve found helpful in helping students think through these systems. 1.  Free Radical Halogenation Think about the classic mechanism for this reaction: Students struggle especially with the second step of the propagation.  If Cl 2 has already been used in the initiation step, how can it be present in the second step of the propagation?  Why not just write CH 3 + Cl• à CH 3 Cl? To answer this question, students need to understand the chemical environment in which the reaction is taking place. When we introduce this in class, I ask students “what’s in the flask?”  I often draw a large flask on the whiteboard, and then ask students to name the different species that are present.  What results is a picture something like this: This image helps students recognize that the reaction vessel is filled with CH 4 and Cl 2 – but only a small amount of radical is present.  This leads to the important follow-up:  What will the CH 3 radical more likely to encounter – a Cl radical or molecular Cl 2 ?  The drawing seems to help students understand the context of the reaction beyond simply the balanced equation.  It also helps drive home the idea that  the propagation sequence occurs until all of the starting materials are consumed. 2.  Mechanisms As a second example, consider the acid-catalyzed dehydration of water.   As we talk through mechanisms, I sometimes gives students a sketch like this:   I usually get plenty of questions from my organic students, like "Why isn’t “H 3 O + ” written in the products?" or "Where does the H 2 SO 4 go?"   And then there’s the test.  Every year, at least one student writes hydroxide as the base that abstracts the H + .  Not in a sulfuric acid solution! The “what’s in the flask” question is a nice way to deal with these questions and misperceptions.  I often lead with an acid-base equilibrium:  Does this equilibrium lie to the right or to the left?  Based on this, what’s in our flask? This leads to some great questions:  Where does the “H + ” written in the first step really come from?  What base is most likely to remove the H + in the last step?  Why is it wrong to show a hydroxide ion pulling off the proton? 3.  Write the reagent Students are sometimes overwhelmed by the myriad of ways that a single reagent can be written.  For example, we want an alkoxide base for an elimination – do we write this as NaOCH 3 , or just CH 3 O - ? Or how about NaOMe/MeOH, or KOMe/MeOH?  If we use ethoxide instead of methoxide, we double the possibilities.  For many of us who teach organic, the casual use of chemical synonyms can be problematic.  In this situation, I again find the “what’s in the flask” technique to be useful.  I like to talk with my students about how these reagents are made, then sketch the components of the flask (i.e., methanol, sodium ion, methoxide ion).  Then we talk about all the different ways this might be written (on my test, on the ACS final, on the MCAT or DAT, etc.), and how to focus on the key features of the reaction. Outlook I was pleased when a student recently asked me to draw a flask on the board and show what was in a solution.  It was an encouraging sign.  While hard to quantify, I think this little technique is positively impacting the way my students think about chemical reactions. ... View more

[originally posted fall 2014] This past semester, I taught a three-credit, standalone laboratory course – Organic Laboratory II.  The class meets once a week, for five hours.   One of the biggest challenges for this course has been optimizing the pre-lab discussions.  If we talk about lab a week beforehand, students often forget the key details by the time the lab arrives.  On the other hand, if I we discuss immediately before lab, students tend to be much less prepared.  Either way, they spend far too much time figuring out what’s going on. This year, I decided to flip the prelabs.  Each week, I made a short video overview of the experiment, featuring key ideas, reactions, mechanisms, safety, and technique.  You can see a sample of the videos below .   I made the videos available about 24 hours before the start of lab, and then include a prelab quiz which is due by the start of lab.   The quizzing can be done using the LMS (both Blackboard and Canvas offer quizzing), or through an online homework system – an especially handy option for labs which are integrated with the course. Video Link : 1783 The results for this class were terrific.   I freed up more of the pre-lab classroom time for spectroscopy, multistep synthesis, and literature techniques, and, as a result, I was able to go deeper with this group than I ever have before.   And I could see a huge difference once we stepped into the lab:  Students know what they were doing, and hit the lab ready to go. ... View more

[originally posted July 2014] One of the first challenges I encountered in flipping a class was how to make short videos specific to a topic I was covering.  I’ve found that for short, low-maintenance videos, Jing is a really valuable resource.  This free download, available from TechSmith, allows you to record up to five minutes of video, then stores it online (also free).  While there is no real editing capability without purchasing the Camtasia software, it is a great resource for its simplicity.  Here's an example of one of my early Jing videos: Video Link : 1779 These days, I mostly use the full Camtasia and edit carefully, but I still use Jing occasionally for a quick and less formal screen capture.  For example, I’ve used Jing quite a bit to show people the basics of navigating around a software package, or to briefly review a topic with which my students should already be familiar.  I can record, upload, and send a link in only five or ten minutes. ... View more