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Stay at Home Laboratories for Chemistry Courses

Jerry Easdon*
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ABSTRACT: Experiments written for students who were quarantined during the COVID-19 pandemic are described. These were
developed to provide hands-on lab experiences that students would not get due to the online nature of course offerings during the
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crisis. The laboratories described include an extraction and oxidation of aldehydes from food items, a study of diffusion of food dyes
in solutions of different pH, and an experiment to determine the optimum temperature of invertase hydrolysis of sucrose.
KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Organic Chemistry, Biochemistry,
Interdisciplinary/Multidisciplinary, Distance Learning/Self Instruction, Hands-On Learning/Manipulatives, Aldehydes/Ketones,
Carboxylic Acids, Dyes/Pigments, Enzymes, Oxidation/Reduction

■ INTRODUCTION
The transition of courses to an online method during the
however, these require assembling kits and sending them to
students.2,3 An article describing a science writing course
COVID-19 pandemic necessitated the development of alter- requires students to write a food preparation as a research
natives to traditional laboratories. This paper describes some of paper.4 A recent post on the organicERs website reflects on
the solutions I employed in a Chemistry of Food, Flavors, and teaching Organic Chemistry I and II laboratories remotely this
Fragrances course. The laboratories contained can also be used spring using animations, videos, data generated by the professor,
for Organic as well as Biochemistry courses. and virtual lab software.5 None of these solutions provided the
The Chemistry of Food, Flavor, and Fragrance course is an actual hands-on lab experience and connections to the course
optional upper division offering for science majors. The course topics which I desired.
did not have a lab component. However, the students this To provide students with projects that still maintained some
semester elected to cover the material during the first half of the hands-on lab work, I developed three stay at home laboratories
semester and then each would do two laboratory-based projects for students to choose from: Extraction and Oxidation of
to illustrate concepts of food chemistry during the last half of the Natural Aldehydes, Diffusion Experiments with Candy Dyes,
semester. The lecture material was based on the text Introductory and Enzymatic Hydrolysis of Sucrose at Various Temperatures.
Food Chemistry,1 and was covered using readings, lectures, and Use of equipment and reagents readily available to students in
class discussions. We had finished this portion of the course and their at-home situation was essential.
students had each proposed two projects just before the In addition, students were encouraged to write and perform
pandemic required the college to move classes online. Samples their own stay-at-home experiment. Samples of student-
of these student proposed projects are as follows: developed laboratories are listed:
• analysis of volatiles from coffee using various methods of • comparison of amounts of casein in milk products
brewing • extraction of flower pigments using solvents of differing
• comparison of amount of estrogen in milk products polarities
• fatty acid composition of different varieties of avocado • electrochemistry with fruits and vegetables
• making pH paper from fruit pigments
• analysis of compounds produced during sugar carameli-
zation • comparisons of sugar content and effect on soda/candy
geyser
• volatile substances produced by cooking meat different
ways During the remainder of the spring semester, students
• casein content in various milk products performed their choice of any two projects from the three I
had developed and from their individual suggestions. They were
These student-proposed laboratories are based on the use of required to keep a standard laboratory notebook and were
instrumentation and laboratory procedures. When the pandemic
caused the college to switch to online instruction, students in the
Food Chemistry course had not begun any of the lab work. The Special Issue: Insights Gained While Teaching Chem-
switch to an online mode away from campus required the ability istry in the Time of COVID-19
of students to do two projects using equipment available at Received: June 17, 2020
home. Revised: July 23, 2020
A review of the literature provided some ideas for potential Published: July 30, 2020
solutions. A few publications describe at-home experiments;
© 2020 American Chemical Society and
Division of Chemical Education, Inc. https://dx.doi.org/10.1021/acs.jchemed.0c00760
3070 J. Chem. Educ. 2020, 97, 3070−3073
Journal of Chemical Education pubs.acs.org/jchemeduc Communication

allowed to submit a formal report, or a PowerPoint presentation, (vinegar). 1H NMR of the isolated vanillin (extracted into
or their laboratory notebook. They were also required to check CDCl3) shows a nearly pure compound. While the students are
in with me weekly on their progress; many of the students not able to run NMR on their samples, the spectra of the vanillin
emailed even more often as they ran into difficulties or shortages. and vanillic acid isolated by this procedure can be provided to
This led to some inciteful discussions typical of the problem- them.
solving nature of laboratory work. Since cinnamaldehyde is a liquid, the extraction is difficult in a
Safety during their project activities was also considered. The home lab. Cinnamaldehyde can be extracted with 70% isopropyl
students were all required to wear safety glasses while doing lab alcohol in a procedure similar to that used for vanillin, but the oil
work. Fortunately, all of the students in this class had taken a obtained is difficult to recover. In this case ground cinnamon is
laboratory safety class we require of our majors as well as having first oxidized with bleach to give cinnamic acid. This is then
taken previous chemistry courses. extracted into base (saturated baking soda) and reprecipitated

■ LAB 1: EXTRACTION AND OXIDATION OF

ALDEHYDES
using 5% acetic acid (vinegar). This solid does not smell like
cinnamon and the NMR indicates fairly pure trans-cinnamic
acid.
Aldehydes are often found as contributors to fragrances of
foods:6 anisaldehyde in anise, benzaldehyde in bitter almond
extract, cinnamaldehyde in cinnamon, citral in citrus fruit, and
■ LAB 2: DIFFUSION OF CANDY DYES IN DIFFERENT
SOLUTIONS
vanillin in vanilla flavoring. Table 1 lists percentages of these Diffusion of food dyes from colorful candies is a popular
aldehydes in the food material. experiment.28−31 As the food dyes diffuse into water from
different color candies, they stay well separated into distinct
Table 1. Percent of Fragrant Aldehyde in Food Item Extracts regions. Where a dye finally reaches another color, mixing does
not occur; sharp well-defined lines divide the regions.
Food Aldehyde Percent (%)
Explanations offered include osmosis, polarity, density,
Aniseseed essential oil Anisaldehyde 0.82−0.927 emulsion formation, colloid formation, and insoluble waxes on
Bitter almond extract Benzaldehyde 978 the candies.32 Since the dyes can be moved in electrophoresis, it
Cinnamon Cinnamaldehyde 3.12−63.89 is possible that these negatively charged dyes repel each other
Lime essential oil Citral 3.1−5.310 and stay separated.33
Vanilla flavoring Vanillin 1.5−2.011 Placement of candies such as Gobstoppers, M&Ms, or Skittles
0.12−0.1812 onto a plate with an aqueous solution is filmed. A timer or watch
is placed in the viewing frame to provide record of time. Students
It seemed reasonable to use odor as an indicator to detect are asked to do this in tap water, acidic solution (vinegar or
success of extraction and of a chemical reaction for fragrant diluted muriatic acid), and basic solution (saturated baking
aldehydes. Several articles describe olfactory-based student soda). In addition, other solutions such as saturated sugar,
experiments.13−24 Extractions of natural products using saturated salt, rubbing alcohol, and vegetable oil can be used for
unmodified espresso machines have been reported;25−27 further investigation. Sample videos are provided as YouTube
however, these procedures require further processing with links. The results in acidic solution show that the dye mixing
reagents not readily available to students in an at-home situation. occurs much sooner than with other solutions, indicating that
The vanillin and cinnamaldehyde extraction laboratories protonation of the negatively charged dyes allows mixing due to
described here use readily available reagents including rubbing minimizing same charge repulsion.

■
alcohol, baking soda, and vinegar. In addition, homemade or
kitchen equipment works for these procedures. The fragrant LAB 3: TEMPERATURE OPTIMUM FOR ENZYMATIC
aldehyde compounds above are poorly soluble in water; SUCROSE HYDROLYSIS
generally aqueous solutions contain ethanol to keep them
dissolved. Their solubility in alcohols and insolubility in water The enzymatic hydrolysis of sucrose and lactose can be followed
can be applied in an isolation procedure. with a blood glucometer.34 Sucrose (table sugar) and invertase
While the extractions do not provide extremely high purity, (as a suspension of baker’s yeast) are readily available and many
the samples can be identified by their pleasant and easily students have access to a blood glucometer. Therefore, I adapted
recognizable odors. Proton NMR (nuclear magnetic resonance) a part of the published experiment asking students to follow the
spectra of substances extracted and oxidized by the at-home hydrolysis at different temperatures to determine the optimal
procedure can be provided to the students and readily show the temperature of the reaction. This required use of a thermometer
expected results. NMR spectra of vanilla flavoring can also be which many kitchens have.
given allowing students to calculate the percent vanillin and Hot and cold water are mixed until a bath of desired
ethanol. temperature is produced, reagents are mixed in the bath and the
Vanillin can be extracted (albeit in low purity) from vanilla reaction is allowed to proceed for 15 min. The reaction can be
flavoring and then oxidized with bleach in the following steps: immediately analyzed or stopped by placing in an ice bath or
(1) evaporation of solvent from the flavoring in a large refrigerator. The initial and final reaction temperature is
crystallization dish (pie pan) over several days, (2) extraction recorded so that students can determine the average. A range
into rubbing alcohol (70% isopropyl alcohol), (3) filtration of initial temperatures from 35 to 70 °C is desirable to produce
(coffee filter), (4) evaporation, (5) identification by odor, (6) the graph of glucose produced vs average temperature.
oxidation with bleach, (7) evaporation to the carboxylic acid,
and (8) use of odor to determine that the vanillin has reacted.
Vanillic acid can be further purified by dissolving in base
■ RESULTS
Students took a strong interest in developing their own at-home
(saturated baking soda) and reprecipitated using 5% acetic acid laboratories. They showed a great deal of creativity in solving
3071 https://dx.doi.org/10.1021/acs.jchemed.0c00760
J. Chem. Educ. 2020, 97, 3070−3073
Journal of Chemical Education

■
pubs.acs.org/jchemeduc Communication

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J. Chem. Educ. 2020, 97, 3070−3073