The Design of a Two-Week Organic Chemistry Course for High

School Students: “Catalysis, Solar Energy and Green Chemical

Synthesis”
Haley Albright, Corey R. J. Stephenson, Corinna S. Schindler

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

15 increased as students gained physical laboratory and research skills.

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

Journal of Chemical Education 5/4/22 Page 1 of 18

25 goal, many institutions and organizations have aligned their sustainability strategies with the United

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

understand fundamental chemistry curriculum through a context of applicability.

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

Journal of Chemical Education 5/4/22 Page 2 of 18

 experience a variety of undergraduate-level laboratory experiments focused on green chemistry and its

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

the specific course objectives are as follows:

60 1. Students will learn and/or review basic chemistry topics (i.e. nomenclature, drawing structures,

acid-base chemistry).

2. Students will perform laboratory experiments and analyze their data.

3. Students will identify green chemistry principles in each experiment and suggest additional ways

to make a reaction more environmentally friendly.

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.

Setting and Participants

75 The “Catalysis, Solar Energy and Green Chemical Synthesis” course has an average enrollment of 15

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

Journal of Chemical Education 5/4/22 Page 3 of 18

 Individual departments within the college of LSA of the University of Michigan refer to the MMSS

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

primarily as white (Table 1).

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,

Mel-Temps, benchtop NMR spectrometers and ovens.

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

Journal of Chemical Education 5/4/22 Page 4 of 18

 lab manual have included: streamlined and outlined experimental procedures to allow for the students

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.

SAFETY AND HAZARDS

The experiments described herein present specific hazards that must be managed by the instruction

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

department, and green chemistry-focused literature reports describing undergraduate-level

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

Journal of Chemical Education 5/4/22 Page 5 of 18

130 of field trips. While safety training has remained as the initial section of the course, the order of

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

natural dye from berries.

Journal of Chemical Education 5/4/22 Page 6 of 18

 YEAR 1: 2015
Day: 1 2 3 4 5

Safety Aldol Transfer Natural Product Click

Reaction Hydrogenation20 Isolation23 Reaction
Amide Bond

OH O Hydrogenation OH H H O NP Isolation citral

SAFETY (from lemongrass)
Et O Et O OR
5 7 5 7
OH O Pd/C OH H H O thymol
(from thyme)
catalyst
Et 5
O Et 5
O
7 7
OH O 176 °C OH H H O
Et 5 O Et 5 O
7 7
castor oil hydrogenated castor oil

6 7 8 9 10

Suzuki Wittig Metathesis Solar Cell Fun

Reaction21 Olefination24 Reaction Assembly22 Day

Suzuki Reaction Wittig Ph

O SOLAR N2
N 160 °C
Br NiCl2(PCy3)2 E/Z ENERGY
Het Ar H
N K3PO4 K3PO4 Ar
ice cream

+ + + G
t-amylOH A
80°C N N Ph PPh3 O M
(HO)2B Het PPh3 E
Cl
S

Addition of field trips

Re-ordered experiments based on complexity
Addition of natural product preparation and presentation
YEAR 5: 2019
Day: 1 2 3 4 5

Safety Wittig Natural Product Tie Dye & Metathesis Reaction26

25 Olefination Isolation Botanical Gardens and Project Prep.
Amide Bond

Amide Bond Formation BOTANICAL Metathesis EtO2C CO2Et

GARDENS N N
H DIC O
N O DMAP Ar Grubbs II
CH3 + N Cl
Ru
H
Ar OH HOBt CH3 Cl Ph
PCy3 EtO2C CO2Et
DMF
resin bead Amide Hoveyda-Grubbs Second
Gen. Catalyst (Grubbs II)

6 7 8 9 10

Aldol Presentations Click Solar Cell Fun

Reaction27 & Industry Tour Reaction28 Assembly Day

O Aldol Reaction Click Reaction

INDUSTRY
O N
CH3 Bn N
NaOH N O Ph
Cu(II) Catalyst N
F N
+O F X
+ "click" N
+ O
Ph Bn
H triazole
X H2O H

145

Journal of Chemical Education 5/4/22 Page 7 of 18

 Figure 1. Initial course calendar from 2015 session and updated course calendar from 2019 session.

Activities highlighted in yellow were added following the 2015 session.

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

uses the Grubbs(II) catalyst.

Figure 2. Incorporation of green chemistry principles in each laboratory experiment.

160 ADDITONAL ACTIVITIES

As per GSI input and student request, additional activities were added to the course schedule. These

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

Journal of Chemical Education 5/4/22 Page 8 of 18

 otherwise be abstract reactions. While some lessons (i.e. nomenclature or acid-base reactions)

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

are outlined in the Supporting Information.

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).

Figure 3. Topics and related activities for added lessons.

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

Journal of Chemical Education 5/4/22 Page 9 of 18

 test using a variety of salts and discussed how they relate to fireworks due to the different colors that

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

to take home with them.

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

edge organic research.

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.

Journal of Chemical Education 5/4/22 Page 10 of 18

 Figure 4. Outline of added activities and field trips.

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

Journal of Chemical Education 5/4/22 Page 11 of 18

 removed prior to 2019. Students found these experiments to be less interactive (as they involved less

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

pursue a career in STEM.

Journal of Chemical Education 5/4/22 Page 12 of 18

 Amide Bond
Amide Bond

Wittig
Wittig

Nat. Prod. Isolation

Nat. Prod. Isolation

Metathesis

Metathesis
Transfer Hydrogenation

Suzuki Industry Tour

Industry Tour
Aldol

Aldol
Botanical Gardens

Botanical Gardens

Click
Click

Solar Cell Solar Cell

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

presentation (which was not rated by the students in closing surveys).

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.

Journal of Chemical Education 5/4/22 Page 13 of 18

265 SUMMARY
In summary, we have designed and optimized a two-week course for high school students to gain

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

they plan to pursue a career in a STEM field.

280 ASSOCIATED CONTENT

Supporting Information
The Supporting Information is available on the ACS Publications website at DOI:

10.1021/acs.jchemed.XXXXXXX. [ACS will fill this in.] Example brief descriptions with file formats

indicated are shown below; customize for your material.

285 2019 Lab Manual (PDF)

Survey Responses and Additional Activities (PDF)

AUTHOR INFORMATION
Corresponding Author
Corinna S. Schindler

290 *E-mail: [email protected]

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

Journal of Chemical Education 5/4/22 Page 14 of 18

 Stephenson group members who contributed to and helped run the course, as well as the many students

295 who have participated in our course over the last 5 years.

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