OrganicERs Facebook Group Discussions about and Contributions for Online Organic Chemistry

It’s been a long semester for everyone with many questions concerning what will happen in the upcoming academic year.  The members of the OrganicERs Facebook group have been sharing their ideas, course materials, and resources in their attempts to provide worthwhile learning experiences for their students.  The following is both a distillation (pun intended) of the discussion and a listing of resources provided by members since the beginning of March for online teaching.  It is divided into three categories:  Solutions for Teaching Lab, Solutions for Teaching Spectroscopy, and Solutions for Teaching “Lecture”.  The latter is in quotation marks because some use active learning in our classes instead of traditional lecture.  Also check the updated Online Resources for Organic Chemistry.

Solutions for Teaching Lab

Like most other faculty around the world, members of the group were forced to convert their courses online with, at best, a week to prepare.   For many, the biggest challenge was converting to an online organic lab.  A favored approach was to use either available videos of experiments, record their own videos, or use available commercial or academic virtual experiments.  Students recorded data, in some cases kept notebooks, and completed reports.  More emphasis was placed on theory.  For technique, it was suggested that students explain what was being done at each step and why and what was happening in the flask. Spectroscopy was used for dry labs.

There were a few suggestions for kitchen chemistry such as paper chromatography and the use of a shoebox polarimeter described by Greenbowe in the Journal of Chemical Education to measure the observed rotation of starch and sugar.

The most popular suggestions for commercial and university sites for virtual lab experiments were

Labster

Beyond Labz

NC State Virtual Reality Organic Lab Experiences

NC State Undergraduate Organic Chemistry Teaching Laboratories - S.M.A.R.T. Lab Videos

ACS Virtual Chemistry and Simulations

 

By far, most posts provided experiments recorded either as videos or exercises with data.  In alphabetical order, here are the contributions from various Facebook group members.

Pamela Auburn suggested the video Diels Alder Reaction with Nick Greeves, pointing out that ChemTube 3D provides animations of the reaction.

Daniel Berger posted the Oxidation of a Bifunctional Alcohol.

Becca Black recorded videos for three reactions.

Synthesis of (E) and (Z)-1-(4-bromophenyl)-2-phenylethene

Reductive Amination: Synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide

Synthesis and Chemiluminescence of Bis[2-(methoxycarbonyl)phenyl] Oxalate

and suggested an open educational resource text.

Dave Blackburn placed the Mohrig Bulky Base experiment at OrganicERs and the Facebook Group Files Repository.

Allison Dick provided videos for a 3-step synthesis of benzoxazine as well as lidocaine

For benzoxazine:

https://youtu.be/odx28HD6tvM

https://youtu.be/nv2xYL6eUPo

https://youtu.be/hPExJSZ4beg

For lidocaine:

https://youtu.be/A2bouOZAZ6s

https://youtu.be/GNtmw8XmuiI

https://youtu.be/r3T1M7Yr7ik

Sapna Gupta prepared a video for SN1 reactions.

Tiffany Hayden suggested Virtual Mass Spectrometry Laboratory.

Armando Herbelin provided videos of organic qualitative tests on Facebook.

Justin Houseknect placed on the OrganicERs website a 3-step synthesis of methyl 3-nitrobenzoate from acetophenone where students will still propose a retrosynthesis, prepare pre-lab notebook pages, and write up a formal lab report on the synthesis and a parallel synthesis of fragrant esters lab (modified from Birney, D. M., Starnes, S. D. J. Chem. Ed., 199976, 1560).  Students are given the boiling points, odors, 1H NMR, and 13C NMR data for 9 esters formed from 3 carboxylic acids and 3 alcohols.

Tony Kiessling’s YouTube channel was suggested.

Peggy Kline posted

Resources for Remote Instruction Post COVID-19 Outbreak which includes experiments for

 Reduction 

 Grignard

 Diels-Alder

 Alkylation

 Arene Diazonium Salt

 Benzoylamino acids

 Esterfication

 Aldol

 Qualitative Analysis

April Royer posted files for a Fisher esterification and an Aldol Condensation.

Laurie Schaffer Starkey provided tutorials of organic techniques, and videos of the Isolation of Eugenol from Cloves with supporting material and Friedel-Crafts Acylation of Ferrocene.  The latter two contain questions to be used for the lab reports.

Cathy Welder suggested Professor Dave Explains on Youtube.  There is a main site and one devoted to organic chemistry. The latter site contains both lecture and lab videos.

 

 

Solutions for Spectroscopy

Resources that can be used for lecture and lab are spectral databases and programs for predicting spectra. Members suggested the following sites and programs. Also, some structure drawing programs have NMR predicting capabilities.

SDBS AIST database (Spectral Database for Organic Compounds, National Institute for Advanced Industrial Science and Technology) is an extensive database of IR, NMR and MS spectra.

NMRdb is a website with tools for predicting spectra 1H NMR, 13C NMR, COSY, and HSQC/HMBC spectra.

At the Sigma Aldrich website, spectra can be found at individual compound listings.

The Notre Dame structure elucidation workbook describes itself as an online workbook “developed for senior undergraduate and graduate students learning to solve the structures of organic compounds from spectroscopic data. Most problems contain an IR spectrum (film or KBr pellet), a 500 MHz 1H NMR spectrum, a 125 MHz 13C NMR spectrum, and a 70 eV electron ionization Mass Spectrum.”  Answers can be viewed at the following locations.

 

http://www.nd.edu/~smithgrp/structure/answers1-32.GIF

http://www.nd.edu/~smithgrp/structure/answers33-64.GIF

http://www.nd.edu/~smithgrp/structure/OSE_Answer_Book.pdf  

Note that these pdf files are easy to find at many locations by simply searches


The Spectral Zoo has IR and 1H NMR for 80 compounds for students to solve.

Biorad KnowItAll Academic Edition provides free chemistry software for structure drawing and spectral analysis.

 

Solution for “Lecture”

Members provided various resources for converting courses to an online format.

This commentary in Inside Higher Education offers 10 teaching strategies to support students and help them continue to learn .

In Chemistry, the ACS student member magazine, posted advise for students taking online courses.

On Facebook there are the Strategies for teaching chemistry online and STEM faculty blundering through remote teaching in a pandemic groups.

You and your students can access The Virtual Model Kit free to draw and manipulate 3D structures of compounds along with other resources.

The Mechanism app from Alchemie is an educational game where students draw mechanisms for a range of reactions.

Open OChem is a site for online homework and assessment which was described at Confchem.  Students are able to draw chemical structures that are automatically graded.

As mentioned under Solutions for Lab, a set of videos can be found at Professor Dave Explains on Youtube.  There is a main site directing viewers to different topics in science and one devoted to organic chemistry. The latter site contains both lecture and lab videos.

Finally, Megan Jacobson polled the group asking what they used for online lectures and tutorials with these results:

    

 Explain Everything 11

 Notability 7

 Doceri 3

 Vittle 2

 One Note on iPad 2

 Record with Macbook 1

  Powerpoint 1

up
15 users have voted.