Hands-on Activity Bridging the Renewable Energy Gap:
Alkane Resources

Learning Objectives

After this activity, students should be able to

• Model molecules using the WebMO website.
• Describe how light hydrocarbons are converted into fuels for transportation.
• Recognize alkanes as compounds composed of carbon and hydrogen.

Educational Standards

Each TeachEngineering lesson or activity is correlated to one or more K-12 science, technology, engineering or math (STEM) educational standards.

All 100,000+ K-12 STEM standards covered in TeachEngineering are collected, maintained and packaged by the Achievement Standards Network (ASN), a project of D2L (www.achievementstandards.org).

In the ASN, standards are hierarchically structured: first by source; e.g., by state; within source by type; e.g., science or mathematics; within type by subtype, then by grade, etc.

NGSS: Next Generation Science Standards - Science

State Standards

Materials List

Each group needs:

• laptop or computer
• web browser, Google Slides
• 50 gumdrops, two colors
• 50 toothpicks (or 25 toothpicks split in two)
• digital camera or phone with camera to take picture of gumdrop molecule

For the class to share:

• laptop or computer
• projector (to show CISTAR and WebMO instruction videos)
• access to the WebMO site: https://www.webmo.net/demoserver/cgi-bin/webmo/login.cgi (see the Procedure for more information)

Worksheets and Attachments

Pre-Req Knowledge

A basic understanding that matter is composed of atoms which bond together to form compounds, which can react and form different compounds.

Introduction/Motivation

How often do you need to ride in a car or a bus to get where you are going? For many people the answer is a lot: especially in suburban and rural areas and places with underdeveloped public transportation infrastructure. People need cars to get to work, to the grocery store, to the doctor, and to nearly everywhere else. But gasoline comes from crude oil, which is expensive, eventually be completely depleted, and is a big contributor toward greenhouse gas emissions. What can we do to stop using so much crude oil?

Do you ever wonder if we will ever resolve these environmental problems? It is scary to think what may happen if we do not. Did you know we are currently relying almost entirely on fossil fuels for transportation? Even though we know those fossil fuels will not last forever. What are some resources that are renewable? (Possible answers: solar power, wind energy, biofuels.) Those resources sound promising, but we do not yet have the technology to use those resources for transportation.

Have you ever heard of shale? Or fracking? (Let students offer answers. Responses will vary.) Shale is a type of rock found underground that is infused with oil that is very similar to petroleum oil. A significant part of that shale oil is known as shale gas. Shale gas contains methane, ethane, propane, and butane. Initially, only the methane part was thought to be useful. (The methane is widely used as natural gas to heat our homes.) The other compounds were treated as waste products! Plus, the other compounds were hard to transport because ethane and propane are gases at room temperature, and they cannot be used as gas in a car, or in the furnaces that heat most buildings.

For decades, we have relied on petroleum that mostly comes from outside of the United States for transportation; however, engineers have now developed the technology to convert those unwanted shale gases into gasoline. We have enough shale gas in the United States to last about 100 years as fuel for transportation. Since current projections estimate we won’t rely on renewable resources, like solar and wind, until about 2060, these shale resources will help us bridge the gap from our reliance on foreign fossil fuels to renewable resources.

Today we will start to learn more about how fuels can be made from shale gas. By the time we are done with this activity, you will be able to tell your friends all about the reactions that transform ethane into butylene, which is the first step in transforming shale gas into octane for our automobiles.

Procedure

Background

Shale is rock formation found underground that is infused with shale oil.  Part of that shale oil is known as shale gas, and it contains methane, ethane, propane, and butane.  The ethane in shale found in the United States is abundant enough to supply our country with fuel for transportation for about 100 years, but it must be converted into fuel for that to happen. This activity will demonstrate the conversion of ethane into butylene.

Before the Activity

• Watch the attached video WebMO Instructions (4:53) to become familiar with WebMO.
• Gather materials and make copies of the Alkane Resources Pre-Quiz and the Project Notebook.
• Prepare sets of gumdrops (50 each black and white) and toothpicks (around 50, or 25 split in two) for each group.

With the Students

Day 1

1. Pass out the Alkane Resources Pre-Quiz to each student.
2. Give students 15 minutes to complete the pre-quiz and turn it in.
3. Divide the class into groups of three each.
4. Show the CISTAR Introduction video: https://www.youtube.com/watch?v=lEZEPE9rdR0
5. Discuss the outlook of converting to renewable resources.
6. Share the Introduction Slides with the students, which are a summarized version of the video. Leave the last slide of the vocabulary definitions on the projector for students to see.
7. Hand out the Project Notebook to each group.
8. Have groups answer the questions for Day 1 in the Project Notebook using the video and presentation information.

Day 2

1. Assign each group an alkane compound from this list:
1. propane
2. 2-methyl propane
3. butane
4. 2-methyl butane
5. pentane
6. 2-methyl pentane
7. hexane
8. 2-methyl hexane
9. heptane
10. octane
2. Have students answer the questions in the first section of Day 2 in the Project Notebook.
3. Show the students how to use WebMO or have them watch the attached video WebMO Instructions (4:53).
4. Give students time to construct their molecules in WebMO. Instructions are in the Project Notebook or below:
1. Go to WebMO Demo Server: https://www.webmo.net/demoserver/cgi-bin/webmo/login.cgi   
2. Log in with these credentials:
1. Username: guest
2. Password: guest
3. Type <enter>
4. Across the top should read “New Job”, “Refresh”, “Download”, etc. 
5. Select “New Job”.
6. Click “Create New Job”. This will go to the “Build Molecule” page.
7. Click the blank screen once for each carbon atom in the molecule.
8. Move the cursor between clicks so the carbon atoms are in a line. 

   

9. Draw a chemical bond between each of the atoms: Click and hold the cursor on the first atom and drag the cursor to the next atom.  Control-Z will reverse any mistakes.

   

10. Select “Build”, then select H for hydrogens.
11. Click the blank screen once for each hydrogen atom, spreading them evenly around the carbon atoms.

    

12. Draw a chemical bond between each hydrogen and the nearest carbon atom.
13. Under “Cleanup”, select “Geometry” to correct the shape of your molecule.

    

14. Under “Lookup”, select “Molecule Info” and record the following information about your molecule:
1. Stoichiometry:
2. IUPAC Name:
3. Molar Mass:

Day 3

1. Ask students to answer the first two questions of the Day 3 portion of the Project Notebook.
2. Pass out one set of 50 gumdrops and 50 toothpicks to each group.
3. Allow each group to decide which colors represent carbon and hydrogen atoms.
4. Have students fill in the table in step three of the Day 3 portion of the Project Notebook with the number of carbon and hydrogen atoms for both ethylene and butylene.
5. Use the gumdrops and toothpicks to model ethylene and butylene molecules. 
1. With their leftover gumdrops, have students design models how ethane can be converted into octane.
2. Have students set up their molecule models with an arrow from the starting products to the ending products.
6. Have them check their reaction model using the Gumdrop Reaction Rubric in the Project Notebook.
7. Have students correct their reaction model until it has a score of at least 8 points.
8. Have each team captain check their reaction model with the teacher.
9. Have students take a photo of their model reaction. 

Vocabulary/Definitions

alkane: Any acyclic saturated hydrocarbon (e.g. methane, ethane, propane, butane, etc.)

chemical reaction: A process, typically involving the breaking or making of interatomic bonds, in which one or more substances are changed into others.

compound: Any substance formed by the union of two or more chemical elements in a fixed ratio, the union being a chemical bond.

element: Any one of the simplest chemical substances that cannot be decomposed in a chemical reaction. Chemical elements consist of atoms which have the same number of protons.

monomer: A relatively small molecule which can be covalently bonded to other monomers to form a polymer.

non-renewable resource: A resource that will not return, or renew, or will only return after a long period of time.

oligomerization: The formation of an oligomer from a monomer.

renewable resource: A natural resource that is replenished by natural processes at a rate comparable to its rate of consumption by humans or other users.

Assessment

Pre-Activity Assessment

Pre-Quiz: Have students take the Alkane Resources Pre-Quiz to gauge their understanding.

Activity Embedded (Formative) Assessment

Notebook: The formative assessment is embedded in Day 1 of the Project Notebook.  It includes these questions:

• Evaluate your own current understanding of the problem:
• Light shale gases like ethane need to be converted into fuels and petrochemicals.  How can that be done?
• What do you know about this problem? 
• What do you need to know about this problem?

Project Vocabulary: Students discuss with their team the main differences, if any, between the meanings for these words that you wrote on your pre-assessment and their actual definition provided in the Project Glossary (last slide in the Introduction Slides). Then score each word from 1-3 for level of understanding.

Post-Activity (Summative) Assessment

Rubric: The Post-Activity Assessment includes a Project Rubric for students to self-assess their gumdrop model of the balanced reaction and a photo of the model for the teacher to evaluate.  The teacher should evaluate the reaction model using the rubric the students use to self-assess their reaction.

Investigating Questions



Copyright

Contributors

Supporting Program

Acknowledgements

This activity was developed as part of a 2021 Research Experience for Teachers (RET) carried out by the Center for Innovative and Strategic Transformation of Alkane Resources (CISTAR). The Principal Investigator was William Schneider, Ph.D., the faculty mentor was Hanyu Ma, and grad student mentors were Neha Mehra and Craig Waitt from the University of Notre Dame.