Allison Dick (Wheaton College)
YouTube Links to Lab Videos Filmed For COVID-19 Remote Teaching
Background:
Like most colleges around the country, Wheaton found itself in the middle of an emergency pivot to remote instruction about halfway through our spring 2020 semester. Organic chemistry is a particularly challenging course to adapt to remote or hybrid teaching for a number of reasons. First, the glassware and chemicals required for experiments are often more expensive, specialized, and hazardous than those used for general chemistry courses. As such, “at-home” experimentation can be more of a challenge without adequate time for creative planning. Additionally, fewer high quality virtual experiments already existed online than for introductory courses. The last 8 weeks of our typical 2- semester organic sequence also contain some of the most complex and interesting experiments, and I did not want our students to miss out on this part of the curriculum. As such, I elected to film myself doing the experiments, complete with real-time, unscripted narration to capture whatever information I deemed important in the moment.
Methods:
I had absolutely zero background in video production or editing prior to this spring. Fortunately, I had upgraded my phone to an iPhone 11 just prior to the COVID lockdown. This provided me with a camera that was perfectly adequate, as well as storage space I needed. My first few experiments were filmed one-handed since I did not yet have a tripod and it was nearly impossible to buy new equipment early in remote instruction. I simply used iMovie to stitch together clips with almost no editing. Later experiments were filmed with a tripod and edited using the educational version of Camtasia. Editing was used simply to highlight important content, and I did not take the time to add intros, music, graphics, or anything fancy (although that would have been fun if my time were unlimited!). In addition to the specific experiments, I desired to create a library of “technique” videos that could be used even in future years to cut down on the time required for in-lab demonstrations, freeing up more time for students to focus on the experiment itself. In organic I especially, these fundamental techniques (melting point, recrystallization, extraction, TLC, column chromatography, and distillation) form the foundation for all future success in the curriculum and are critical for students to master.
Any instructor is welcome to use any of these videos if they fit into your curriculum. I am also happy to share Word or PDF files of lab manual sections that go with specific experiments, if desired. You may modify the files to fit your needs, but please acknowledge Wheaton College somewhere. Thanks!
Technique/demo videos
•Melting point sample prep and demo (SLIGHT EDITS) https://youtu.be/38tVykx6quA
•Extraction demo https://youtu.be/DoAsbVoYF0E
•TLC demo (EDITED) https://youtu.be/EV86d0XgAGQ
•Recrystallization demo (SLIGHT EDITS) https://youtu.be/g6MVrJx6bjc
•Flash chromatography demo (EDITED) https://youtu.be/Aw9EQ-YLuMQ
•Distillation demo https://youtu.be/B3po_y97fWU
•IR sample prep and acquisition (PerkinElmer Spectrum II) https://youtu.be/zz4ry5jHJJE
•NMR sample prep, acquisition, etc. (Nanalysis 60 MHz) https://youtu.be/UF46vX9BjRs
•Use of a rotary evaporator https://youtu.be/YT4k98igunE
•Intro to polarimetry https://youtu.be/BxX8syYefdo
Organic I experiments (for fall 2020)
•Brief melting point experiment (pure substances vs. mixtures) (assisted and narrated by lab manager Melody David): https://youtu.be/RHTuaaVJgis
•Recrystallization of p-phenylphenol (including small scale solubility tests and melting point data before and after): https://youtu.be/4H3rty1GuYQ
•Extraction and TLC (separation of a three-component mixture of lidocaine, p-phenylphenol, and biphenyl by acid/base extraction, analysis by TLC; SLIGHT EDITS): Part 1 separations https://youtu.be/iuhjqnirS4E, Part 2 isolations: https://youtu.be/1XxRNDkig0Y, Part 3 TLC analysis: https://youtu.be/IkIXcyztF40
•Column chromatography (separation of ferrocene and acetylferrocene): https://youtu.be/Es2EGGrAWKk
•Fractional distillation of MeOH/water mix (enough data to plot a graph of head temp vs. volume distillate) (assisted and narrated by lab manager Melody David): https://youtu.be/QMjV5KLUWj0
•Isolation of trimyristin from nutmeg (MINOR EDITS): https://youtu.be/ywcNXETqYLI
•Resolution of phenylsuccinic acid with L-proline: https://youtu.be/epfJtX5khi0 (experiment); https://youtu.be/h_pZ0kj2o1A (polarimetry)
•Hydroboration of styrene: https://youtu.be/ocSiQYDIR04 (experiment); https://youtu.be/la9-X4-0tGA (gas chromatography)
•Catalytic hydrogenation of p-anisalacetophenone (monitoring the reaction by TLC, purification by recrystallization): https://youtu.be/H9VwVe0ZqrY
•Synthesis of tert-butyl chloride from tert-butyl alcohol (SN1 reaction, purification by distillation): https://youtu.be/QFydMQtZVtU
Organic II experiments (Mostly filmed for spring 2021)
•Diels-Alder reaction of maleic anhydride and cyclopentadiene* https://youtu.be/03KKrq9viLI
•Electrophilic aromatic substitution 1: Bromination of acetanilide https://youtu.be/KQoQf516UuY 2: Chlorination of 4-bromoacetanilide (and TLC for both) https://youtu.be/fxEegvrlWwY
•Grignard addition of PhMgBr to acetophenone: https://youtu.be/H-gEB9fbO3U
•Dehydration of methylcyclohexanols: https://youtu.be/l2ALaNatSNs
•Sodium borohydride reduction of camphor: https://youtu.be/l7Dmdm9zOXk
•Multistep synthesis of a benzoxazine (imination, borohydride reduction, Mannich-like reaction) (no Camtasia edits, from spring 2020) Imination: https://youtu.be/odx28HD6tvM, Reduction: https://youtu.be/nv2xYL6eUPo, Mannich: https://youtu.be/hPExJSZ4beg
•Wittig synthesis of stilbenes: https://youtu.be/41u16DSwIMU
•Aldol condensation (REFILMED for 2021): https://youtu.be/NngHP3-Nfqg
•Synthesis of Lidocaine (2 parts, no Camtasia edits, from spring 2020): Part 1 https://youtu.be/A2bouOZAZ6s, Part 2 https://youtu.be/r3T1M7Yr7ik
*MAY eventually be refilmed in January. Noticed during edits I partially blocked the camera a fair bit.
Bonus videos (no Camtasia edits): Preparation and solvatochromism of a merocyanine dye (from my advanced synthesis class in fall 2020) Synth 1: https://youtu.be/QDBQX_NCGH0, Synth 2: https://youtu.be/FdtYjhWuqtk, Synth 3: https://youtu.be/fx-vZkv89FE, Solvatochromism: https://youtu.be/6cybq4MtwRs
Pedagogy:
Although I absolutely acknowledge that nothing can replace hands-on experience in the lab, that has not always been an option available to students during COVID. We were fully remote during the second half of spring 2020, and we had to split our lab sections into cohorts in the fall to accommodate social distancing. This meant we could run only half of our normal labs in person. Additionally, a small number of students elected to continue their education fully remotely and never set foot in a lab this fall, and we had to be prepared for students in quarantine. My desire was to provide as consistent and seamless an experience as possible for all students, regardless of modality. As such, each of them purchased the same laboratory manual. Each experiment was either performed by the students in the lab, or experienced through the videos. The other organic instructors and I also used screencasting to record pre-lab “lecture” content to highlight important points. Even for the recorded experiments, students were instructed to make observations, record data, and analyze provided spectra, as though they were performing it themselves. Although we experimented with targeted post-lab questions in spring semester 2020, this fall we ultimately decided on more open-ended reports for all experiments, following the same format for both in-person and recorded modalities.