The Design of A Two-Week Organic Chemistry Course For High School Students: "Catalysis, Solar Energy and Green Chemical Synthesis"
The Design of A Two-Week Organic Chemistry Course For High School Students: "Catalysis, Solar Energy and Green Chemical Synthesis"
The Design of A Two-Week Organic Chemistry Course For High School Students: "Catalysis, Solar Energy and Green Chemical Synthesis"
5 Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
ABSTRACT
A two-week summer camp was designed, implemented, and then updated for high school students
focusing on organic chemistry, solar energy, and green chemistry principles. Students learn about
laboratory safety, perform organic reactions, go on field trips, and take part in interactive lessons that
10 focus on both fundamental chemistry topics as well as green chemistry. Each lab experiment
implements at least one green chemistry principle by reducing waste or reagent use while employing
additional safety measures. The course has been edited and modified based on student feedback to
include additional lessons, field trips, a student presentation, and other activities. Responses to post-
course surveys provided feedback on each component and also indicated that student interest in STEM
GRAPHICAL ABSTRACT
KEYWORDS
General Public, High School / Introductory Chemistry, Organic Chemistry, Laboratory Instruction,
20 Curriculum, Hands-On Learning, Catalysis, Green Chemistry, Natural Products, Reactions, Synthesis.
INTRODUCTION
The importance of sustainability and green chemistry became widespread in the early 1990s and
particularly in the United States after the passage of the Pollution Prevention Act of 1990.1 Toward this
Nations Sustainable Development Goals (UN SDGs), which is a set of goals that aim to improve the life
of all people and the planet.2 Scientists, including chemists, must be trained to adopt green chemistry
practices and techniques in order to solve problems while keeping human health and the environment
in mind as they perform their research. Ideally, this mindset should be established in the earliest stages
30 of training and education.3,4 The implementation of these practices in education and curriculum,
however, has only recently become more widespread5 and the number of publications on green chemistry
education has steadily risen since 1998.6 Many educational programs across the country have attempted
to fully integrate green chemistry principles into their curriculum, created a separate green chemistry
course, chosen a textbook with chapters focused on green chemistry,7 or used greener experiments in
35 their laboratory courses.8,9 The ability to include green chemistry concepts allows students to
One way to increase interest in green chemistry at an earlier stage is to provide opportunities to
younger students via programs that allow them to experience the curriculum of upper-level collegiate
classes that embrace these principles and also, to encourage them to learn about scientific applications
40 in everyday life. A few programs designed for high school students incorporating an early interaction
with chemistry include the University of Minnesota’s “Polymer Day”10, the Anson L. Clark Scholars
Program at Texas Tech University11 and Beyond Benign,12 a foundation focused on green chemistry
education offering a variety of resources for educators, including those specifically teaching at the K-12
level. These programs and resources for educators13 are examples of efforts to bring science to high
45 school students by directly sharing research and scientific resources while creating educational
networks. The University of Michigan offers a summer program for high school students called the
Michigan Math and Science Scholars (MMSS) program14 which is designed to introduce students to
current developments in science research, specifically at the University of Michigan (UM), and to inspire
an interest in mathematics, engineering, and the sciences. MMSS offers a variety of STEM-focused
50 courses designed and led by university faculty15 and graduate students. We have designed a course titled
“Catalysis, Solar Energy and Green Chemical Synthesis” and it was first offered in the summer of 2015.
The course was created to provide the unique opportunity for high school students to learn and
application in organic reactions. The theme focuses on the explanation and implementation of alternate
55 energy sources and the 12 principles of green chemistry16a in a laboratory setting as well as in industry.
COURSE DESIGN
Course Objectives and Theme
The overall goal of the course is to provide an interesting and exciting experience for the students and
60 1. Students will learn and/or review basic chemistry topics (i.e. nomenclature, drawing structures,
acid-base chemistry).
3. Students will identify green chemistry principles in each experiment and suggest additional ways
65 4. Students will gain insight into the undergraduate experience in a STEM course.
The course is designed to focus on methods and synthetic techniques surrounding the 12 principles
of green chemistry developed and published on by Dr. Paul Anastas and Dr. John Warner17 and adopted
by the American Chemical Society (ACS).16b While the title and theme of the course is “Catalysis, Solar
Energy and Green Chemical Synthesis”, another major aspect of the course is the opportunity for the
70 students to take away an overall experience of undergraduate life and coursework as a STEM major. By
providing upper-level experiments that are commonly offered in 200-level laboratory courses for
students majoring in STEM fields, the students not only learn new information, but they gain new skills
prior to what they would otherwise experience in their early years of college.
high school students, per two-week session, and is offered twice over the summer with students meeting
in the laboratory for two 3-hour sessions each weekday. Alternate activities are provided by the MMSS
program over the weekend and students are housed in the UM dormitories or commute to campus each
day. No prerequisite courses or preparation is required prior to attendance. The MMSS program utilizes
80 a rolling admissions system for enrollment and also offers need-based financial aid opportunities.18
program that many of their faculty participate in via respective outreach links on the faculty websites.
Students range from ages 14-17 and are primarily rising sophomores and juniors (Table 1, below).
Additionally, an increasing number of international students have participated over the last 5 years and
85 the ratio of male to female students has remained approximately 1:1. In 2019, over half of the total
enrollment in both sessions were students of Asian ethnicity with the remaining students identified
Table 1 includes data on the high school students, including: school year, country of origin, ethnicity,
90 and gender.
The course is primarily led by graduate student instructors (GSIs) from the chemistry department at the
University of Michigan. Two GSIs lead each day of lab experimentation with at least one new GSI per
day to increase contact with graduate students of different backgrounds and specialties. The
experiments are performed in an undergraduate teaching laboratory in the chemistry building at the
95 University of Michigan that is equipped with basic micro-scale glassware, fume hoods, IR spectrometers,
Course Text
A lab manual was written and has since been updated to reflect any additions and changes to the course.
It includes a short introduction to the course, detailed instructions and background for each experiment,
100 and follow-up questions for students to answer during and after the conclusion of the experiment.
Reference tables and additional information are also included in the manual. The main updates to the
to have more straightforward instructions, additional space for notes, data and observations, and step-
by-step tutorials for basic lab techniques and calculations, such as TLC and dimensional analysis. The
105 complete and most recent version can be found in the Supporting Information.
staff. These hazards include the use of flammable, corrosive and toxic reagents and solvents (i.e.
hexanes, DMF, NaOH pellets), exposure to high temperature surfaces (100-150 °C hot plate and
110 distillation set up), and the handling of glass and sharp objects. To minimize overall student exposure
to the aforementioned hazards, the instructors handle most of the hazardous tasks by setting up hot
plates and distillation glassware along with dispensing the most toxic reagents such as NaOH. Students
begin the course with an extensive safety training session and safety scavenger hunt that requires them
to find the location of various items in the laboratory (i.e. fire extinguisher, eye wash, exits, and other
115 equipment) in order to familiarize themselves with the lab space. The safety training session was
designed based on the protocol used by the UM Chemistry Department for undergraduate teaching
labs.19 Additionally, each experiment begins with a discussion of the specific hazards related to its set
up, reagents, and work up and aims to recognize hazards, assess and minimize the risks of those
hazards, and prepare the students for possible emergencies or accidents. All experiments are performed
120 in a fume hood and proper PPE (lab coats, goggles, gloves, long pants, and closed-toed shoes) is worn at
all times, aligning with the lab safety requirements outlined by the UM Chemistry department. More
detailed safety information for each experiment is outlined in the lab manual in the Supporting
Information.
EXPERIMENTS
125 The experiments for the course were developed by graduate students and based on the following: ongoing
research in the department, previous experiments from 200-level organic chemistry labs in the
experiments. The initial course schedule displayed in Figure 1 has been optimized to the most recent
version based on the timing or length of experiments, level of difficulty and complexity, and the addition
experiments was altered to reflect an increase in difficulty both in knowledge and technique. For
example, the Wittig reaction utilizes only solid reagents and no solvent, as the students grind the starting
materials together in a mortar and pestle.24 The aldol reaction27 is better suited for a later experiment
as it employs micro-scale amounts of reagents, requires a liquid-liquid extraction work up, and multiple
135 analytical techniques that must be taught beforehand. By placing the more advanced experiments later
in the course, the students performed better by utilizing their new lab experiences and recent technique
development. Additionally, experiments like the Transfer Hydrogenation reaction20 and Suzuki reaction21
were eliminated based on low student ratings in closing surveys. As one of the other main topics of the
course is solar energy, the last activity that the students do in the lab is to create their own solar cell
140 and to learn about alternative energy sources. The solar cells are assembled from a kit22 that uses
relatively benign materials so the students can take the cells home with them. The solar cell kit is
distributed by the Institute for Chemical Education (ICE) through the University of Wisconsin-Madison
and allows students to build a solar cell that generates electricity from the absorption of solar energy by
6 7 8 9 10
+ + + G
t-amylOH A
80°C N N Ph PPh3 O M
(HO)2B Het PPh3 E
Cl
S
6 7 8 9 10
145
As the theme of the course is focused on green chemistry, the course was designed to incorporate
some greener practices in the experiments. Figure 2, below, describes how many of the principles are
150 implemented or discussed throughout the course. The use of solvents is minimized or eliminated, as in
the case for the Wittig reaction,24 to prevent waste. The discussion of atom economy is mentioned early
in the course but best displayed in the aldol reaction where all carbon atoms from the starting materials
are maintained in the aldol product. Additionally, the input of energy to perform the reactions is also
minimized. Therefore, few reactions are heated, and the Wittig reaction is not stirred by a mechanical
155 stir plate but ground by hand in a mortar and pestle. Significant catalytic reactions are also utilized,
specifically the Click reaction28 which employs a copper(II) catalyst and the metathesis reaction26 which
additional activities included lessons on fundamental chemistry topics such as: nomenclature, drawing
structures, acid-base reactions, periodic trends, and analytical techniques (see Figure 3) during the
waiting periods or “down time” of an experiment. By adding in these lessons, students were able to get
165 more out of the experiments with an increased understanding of structure and reactivity in what would
represented review material for the older students that had already taken chemistry courses at their
high school, they allowed for a more “even playing field” for the younger students. The students were
able to expand their scientific vocabulary allowing for more critical thinking about the transformation
170 itself when it came to analyzing reaction outcomes and experimental directions. Each lesson was
accompanied by an activity that ranged from a worksheet to a group discussion or a game that
incorporated what they had just learned (Figure 3). This allowed for the students to practice a few
examples of each topic and interact with more of their peers during the lab session. Most students
provided comments about these lessons in the closing surveys, showing their appreciation in helping
175 them prepare for any upcoming chemistry courses in high school and college. These additional activities
A chemistry laboratory course is often stressful for students at the collegiate level so it would be
unsurprising that high school students partaking in a similar course with new classmates in a university
chemistry laboratory might also feel intimidated. In order to alleviate some of this stress for the high
180 school students, themed games were added as a more relaxing and fun way to learn chemistry terms
and facts. Some of these games included chemistry-themed word searches, element spelling races,
chemistry jeopardy, and the making of liquid nitrogen ice cream29 on Day 10 (Fun Day).
185 The incorporation of chemical demonstrations was also well-received by the high school students.
Apart from the demonstration by the GSI of the reaction set up or a technique necessary for a particular
experiment, real-world application demonstrations were a good way to spark interest in some of the
otherwise not viewed or seen chemical phenomena in everyday life. For example, we performed the flame
190 are created when the salts are burned.30 Additionally, things like the gummy bear combustion31
experiment and silver mirror in a bottle experiment32 were popular. A chemical demonstration on the
history and use of dyes was implemented via the t-shirt tie-dye33 activity that the students were also
able to participate in (Figure 4). This also allowed students to create their own design on a MMSS t-shirt
195 We have recently incorporated the use of benchtop NMR analysis into the lab experiments.
Previously, the high school students had only been able to utilize TLC, IR spectroscopy, and melting
point determination to analyze their products from the experiments. Short lectures and demonstrations
are given on how to perform all of these types of analyses as well as an explanations and worksheets
describing how to interpret the data. The use of the 60 MHz benchtop NMR in the teaching lab allowed
200 students to perform high level analysis that even most undergraduates do not have the opportunity to
do outside of a research setting. While this is a complex topic to learn without a strong background in
chemical structure, it was a fitting example of what chemists use on a daily basis as they perform cutting
Additionally, a long-term project was incorporated into the curriculum. Students were asked to put
205 together a 10-minute PowerPoint presentation on an impactful natural product. They were assigned a
molecule, such as caffeine, vitamin B12, tetrodotoxin, etc. and given directions on how to put together
a presentation including suggestions on where to look for information on the use, discovery, and
synthesis of the molecule. This project was assigned in the first few days of the two-week course and
then presented in the last 2-3 days, allowing time for the students to put the presentation together and
210 practice their delivery. Dedicated time during the lab sessions was included for students to work on
their presentations with GSIs present to allow for students to ask questions and to minimize outside lab
expectations.
215 The addition of field trips to industrial companies in the greater Ann Arbor area to Dow Chemical
Company or Cayman Chemical, was added in 2016 to allow for the students to gain information on
possible career paths in chemistry. The companies provide tours of their facilities, presentations on what
they research or manufacture, and offered some parting information on their outreach services for high
school and college students. The students also visit the Matthaei Botanical Gardens and Nichols
220 Arboretum34 in Ann Arbor, each year. This trip connects well with the natural product presentations as
most of the molecules that the students research and present on are isolated from plants that the
gardens cultivate and maintain on the grounds. The students are sent on a scavenger hunt to find as
many of these natural product-containing plants as possible and it also encourages them to explore the
medicinal plant garden to learn about even more biologically active molecule-containing plants (Figure
225 4).
STUDENT PERCEPTIONS
The students were given closing surveys inquiring about their thoughts on each experiment, the overall
program, the use of the field trips, and their interest in pursuing STEM majors in the coming years. The
survey data relating to the rating of activities for the 2016 and 2019 sessions is displayed in Figure 5,
230 below. The most popular laboratory experiments were the natural product isolation and solar cell
assembly. This is due to the real-life applications and relationships that these experiments contain. The
two experiments with the lowest ratings in 2016, Transfer Hydrogenation and Suzuki Reaction, were
set up and manipulation) and the reaction concepts were less accessible due to their complex catalytic
235 processes.
The students enjoyed the field trips to the botanical gardens and local industries (rated highly in
both sessions, see Figure 5) as not only an opportunity to take a break from the lab but to gain more
real-world application and information about future career opportunities. The ability to have both
educational and casual interactions with the GSIs over the two-week period was also highly commented
240 on as a positive aspect that allowed the high school students to gain insight into the paths of STEM
majors in college, graduate programs and what options can come from the various degrees. For the most
recent session in 2019, one GSI was kept constant with one rotating GSI allowing for students to
continue to meet multiple graduate students with a variety of backgrounds, ethnicities, and pathways
to chemistry, but also allowed for the expectations of daily lab and course etiquette to be more
245 consistent. Many students also commented on their appreciation for the course to offer a less stressful
introduction to undergraduate chemistry lab work as this was not a graded course that most students
experience for the first time in their early years of college. Across the board, students indicated that
their interest in science was increased following the experience with most indicating that they plan to
Wittig
Wittig
Metathesis
Transfer Hydrogenation
Industry Tour
Aldol
Aldol
Botanical Gardens
Botanical Gardens
Click
Click
250
Figure 5. Student feedback on laboratory experiments and course activities. A. Responses from 2016
session that included additional experiments and the initial implementation of field trips. B. Responses
from 2019 session following the removal of low-rated experiments and addition of the natural product
255 To investigate the students’ understanding of chemistry and gain insight into their general opinions on
science, we prompted the students to answer the following question in their closing surveys. “How has
this experienced changed your opinions on chemistry and science, in general?” Many of the responses
from the high school students expressed their increase in overall interest in chemistry after completing
the course. A few students commented on their new appreciation for the work that chemists do on a
260 daily basis and that they were surprised to learn “that chemistry is a huge part of everyone’s life and
that chemistry enhances these lives.” Some students also stated that their understanding of the
scientific method was realized as this course “has shown me that creating new reactions is a bit about
trial and error” or that they are able to relate the ability to help others and the planet through green
chemistry practices. Complete student responses are included in the Supporting Information.
experience in undergraduate-level organic chemistry course work with a focus on the principles of green
chemistry and solar energy. The course has been updated to increase reflection on the green chemistry
principles and by adding fundamental chemistry lessons to encourage more background understanding
270 of experiments. Students were able to perform undergraduate-level chemistry experiments and analyze
the data that they collected by employing their newly learned laboratory skills and techniques.
Additionally, this course was able to offer the opportunity for students to gain insight into the
undergraduate experience at the University of Michigan and most students indicated their interest in
applying to UM in the future. Future changes to the course may include an added emphasis on student-
275 centered analysis of green chemistry and how it is implemented in the course or an added section in the
lab manual for an assigned lab write-up that would more closely simulate a written lab report assigned
in an undergraduate lab course. In conclusion, we have achieved our overall goal to communicate
science at an earlier stage and increased student interest in STEM with most students indicating that
10.1021/acs.jchemed.XXXXXXX. [ACS will fill this in.] Example brief descriptions with file formats
AUTHOR INFORMATION
Corresponding Author
Corinna S. Schindler
ACKNOWLEDGMENTS
This work was supported by the National Science Foundation (CHE-1654223) and by the Michigan
Math and Science Scholars program. We gratefully acknowledge the numerous Schindler and
295 who have participated in our course over the last 5 years.
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