Teaching Organic Chemistry I and II Labs Remotely during a Pandemic
As with many other institutions, Dartmouth College moved to remote teaching in March due to the COVID-19 pandemic. However, since Dartmouth operates on a quarter system, we started the spring term remotely after narrowly completing the winter term. Our main sequence organic chemistry students were enrolled in Organic I for the spring, while our honors sequence students were enrolled in Organic II. I was faced with how to teach the full term of Organic I lab remotely to students who had never set foot in a physical lab space. I know many of you finished the Organic II semester this year and face the possibility of remote learning for Organic I in the fall. As such, I wish to share a bit regarding what I did this spring in the hopes of spurring ideas for your fall. I will also describe my experience teaching the Organic II lab.
Of course, my first step was to determine what it was I wanted students to be able to do after completing the remote labs. I had to shift the focus from hands-on skills to theory, and in some cases, watching a video of someone else performing the experiment and using the resulting raw data to generate a report. I tried to balance assigned readings from a lab book with videos. Some videos were cartoonish but covered the theory well. For each experiment, I looked for photos and/or videos of actual glassware, too.
Students were asked to keep notebooks that were similar to what would be kept in a face-to-face setting. After all, some of the desired learning outcomes regarding maintaining a lab notebook are completed outside of the lab. So, students entered an experimental title, the objective, and the date. They included chemical reactions when appropriate, a reagent table, safety information as if they were working with the compounds in the lab, the planned procedure, and references to all resources.
To help relieve student stress and to make grading a bit easier, I elected to provide worksheets that clearly laid out what was to be included in each writeup in addition to their scanned notebook pages. For example, the first experiment was a TLC lab on over-the-counter analgesics. The corresponding worksheet had a section in which a sample Rf calculation was to be entered. A fill-in-the-blank Rf table was then provided with analgesic names already listed and a place for them to enter the solvent system and the identity of the unknowns. There was a prompt for a discussion section (limited to 100 words) and reminders on the worksheet to answer post-lab questions and include citations. A breakdown of the grading scheme was also included.
I found Lisa Nichols’ Organic Chemistry Lab Techniques textbook to be an extremely valuable resource. It is an open resource that covers many of the techniques I teach and includes many, many images.
I used only a few go-to sources for video tutorials. One was Laurie Starkey’s lab tutorials. Another was the Organic Chemistry section posted under Professor Dave Explains in YouTube. I discovered a few videos on the JoVE Science Education Database, but I found several of those videos to feel like documentaries recorded in the 60’s. Additionally, JoVE was only available for free for a limited time during the pandemic. It was not a resource I would pay to use. Tony Kiessling has a rather extensive YouTube playlist as well, and I used his lectures on the dehydration of 2-methylcyclohexanol, as that is an experiment we would have carried out had we met face-to-face. Additionally, I had previously filmed a few introductory techniques videos, some less than two minutes in length, to aid students in their pre-lab preparations. Links to many of those videos are included at the end of this article.
Raw data were provided for some experiments. TLC plates drawn in ChemDraw for the analgesics experiment, gas chromatography data from the dehydration experiment, and fractional distillation data for 5 sets of samples from a whiskey flavoring components lab were provided. Raw NMR data was also provided for an experiment as students were able to use the department’s NUTS site license to process the FIDs. PC users were able to install NUTS on their machines. Other users were able to log into a Dartmouth server using Microsoft Remote Desktop where they were able to access the NUTS program and representative data files.
For the Organic II lab, students purchased a Beyond Labz license, which cost less than the normal lab fee which was waived. The app has virtual benchtops for general chemistry, organic chemistry, biology, and physics. I found the organic synthesis lab resources to be extensive. They have numerous procedures that can be carried out using reagents in their stockroom. Doing an experiment incorrectly will give the corresponding incorrect data or might lead to an explosion of the round bottom flask (rbf)! Users can monitor reactions by TLC and obtain mp, NMR, IR, and MS data of the products they synthesize. (Spectra are from the Sigma-Aldrich library.) Beyond Labz offers a 2-day free trial which can be extended upon request. The benchtop was not intuitive to me but reading the provided help documents made everything clear. As such, I advised my students to read before beginning, and I provided a handholding document for getting started that I am willing to share. The app is meant to be an inquiry-based pre-lab supplement to actual experiments, but I found it to be a good option while the labs were closed. Beyond Labz also shared the procedure files as a Word document so that I could edit them in any fashion I saw fit.
For me Beyond Labz did not seem appropriate for a remote Organic I lab experience. There are no techniques labs or exercises, only syntheses and qualitative tests, though the synthetic options do include Organic I topics. The app uses standard taper glassware, which students had not previously used. When working up a reaction, one simply drags a separatory funnel to the rbf and contents of the rbf automatically move into the funnel. Selecting an aqueous layer for wash or extraction causes diethyl ether to miraculously appear in the funnel too. If you then click on and drag the organic layer out of the funnel, another rbf appears that contains only the reaction product, where drying and evaporation magically occurred without any additional action of the user. If you want your students to be able to carry out virtual reactions in Organic I, you could provide additional guidance regarding what is happening that is not explicitly obvious.
In addition to the virtual labs, I had Organic II students watch 3 experiments carried out by Rebecca Black and make notebook entries as if they had carried out the experiments themselves. Rebecca provided NMR spectra that I had students analyze.
- Synthesis of (E) and (Z)-1-(4-bromophenyl)-2-phenylethene (a Wittig reaction) https://www.youtube.com/watch?v=-e5gL3tHr48&feature=youtu.be
- Reductive Amination: Synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide https://youtu.be/CpIFY_ECyCo
- Synthesis and Chemiluminescence of Bis[2-(methoxycarbonyl)phenyl] Oxalate https://youtu.be/cxyE-11_iuE
I did find it advantageous for both the Organic I and II labs to use the first week to access and install the various technical components. Students needed to find a PDF generator, and I recommended the free GeniusScan app. Many needed to install Zoom and ChemDraw. For model kits I pointed them to inexpensive sets I like on Amazon in addition to the CheMagic virtual model kit. They also needed to download the Nichol’s techniques manual and install or access NUTS.
I would be happy to share more details. Feel free to contact me at email@example.com.
Nichols’ Organic Chemistry Lab Techniques textbook https://open.umn.edu/opentextbooks/textbooks/organic-chemistry-laboratory-techniques
Laurie Starkey’s lab tutorials
Professor Dave Explains YouTube channel
Tony Kiessling’s YouTube channel
Beyond Labz ($25/student/yr for installation on only one device.)
Rebecca Black’s materials (firstname.lastname@example.org)
To request more information from Rebecca, use this Google form: https://forms.gle/PdXS8RXGYqESYNpMA
CheMagic virtual model kit
My technique videos
- TLC Supplies (1:55) - https://dartmouth.techsmithrelay.com/1qMR
- TLC Spotting and Developing (4:08) - https://dartmouth.techsmithrelay.com/fQJy
- Pipet filtration (1:21) - https://dartmouth.techsmithrelay.com/7RHx
- Fluting Filter Paper (3:22) - https://dartmouth.techsmithrelay.com/lkoZ
- Melting Point/DigiMelt (4:20) - https://dartmouth.techsmithrelay.com/QJsw
- Fractional distillation setup (13:18) - https://dartmouth.techsmithrelay.com/gLD1
- Column Chromatography (16:00) - https://dartmouth.techsmithrelay.com/2Fhc
- Rotary Evaporation (8:10) - https://dartmouth.techsmithrelay.com/ysub
- Extraction (5:55) - https://dartmouth.techsmithrelay.com/oaVr
- NMR Sample Prep (3:25) - https://dartmouth.techsmithrelay.com/k3e7