Chemistry of Alcohol

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Chemistry of Alcohol

Developed by

Tom Good

Cooperstown High School

Cooperstown, New York

For the


My Environment, My Health, My Choices project

University of Rochester

Rochester, NY


Abstract:
Methanol and ethanol are both metabolized (oxidized) into an aldehyde and then an organic acid. Why then is methanol more toxic than ethanol? Should a Breathalyzer be used to screen for drinkers at school events? Using a Web Quest (or alternatively using a directed study), a molecular model building activity and making a class presentation for a Board of Education meeting are all part of this organic chemistry environmental health science four day lesson.

Table of Contents


Pre/Post Test

3-4

Answer Key for Pre/Post Test

5-6

Learning Context and Classroom Timeline

7

Day 1: Part 1—Introductory Article

8-9

Day 1: Part 2—Web Quest

10-15

Day 1: Part 2—Alternative If Internet Not Available

16-32

Sample Answers to Web Quest

33-36


Day 2: Molecular Modeling Activity

37-43

Day 3 and 4: Board of Education Presentation

44-46

New York State Learning Standards

47-49



Teachers, we would appreciate your feedback. Please complete our brief, online Environmental Health Science Activity Evaluation Survey after you implement these lessons in your classroom.

The survey is available online at: www.surveymonkey.com/s.asp?u=502132677711

Pre/Post Test Name ______________________
1. What is the common name for ethanoic acid?

1. acetic acid

2. ascorbic acid

3. lactic acid

4. salicylic acid
2. What is the IUPAC name of the compound that has the condensed structural formula H2CO?

1. methanal

2. methanol

3. hydrogen carbon (II) oxide

4. dihydrogen carbon monoxide

3. Which compound has chemical properties most similar to the chemical properties of ethanoic acid?

1. C2H5OH

2. C2H5OC2H5

3. C3H7COOH

4. C2H5COOC2H5

4. Given the balanced equation for the mild oxidation of CH3OH :
2 CH3OH + O22 H2O + 2 HCHO
What is the functional group of the organic product produced?

1. acid


2. alcohol

3. aldehyde

4. ketone
5. When considering toxic substances, LD50 is a term that often appears. What do the letters, “LD” represent in the term LD50?

1. legally dead

2. learning disabled

3. lethal dose

4. limited degree

6. Given the structural formulas of four organic compounds



Which pair contains an alcohol and an acid?

1. a and b

2. a and c

3. b and d

4. c and d

7. When applied to measurements, what is the meaning of the statement, “Your precision is good but not your accuracy?”

1. Your values are close to the true value and are close to each other.

2. Your values are close to the true value but are not close to each other.

3. Your values are not close to the true value but are close to each other.

4. Your values are not close to the true value and are not close to each other.

8. When ethanal is converted into ethanoic acid, which statement describes what happens in the reaction?

1. Ethanal loses one oxygen atom to become ethanoic acid.

2. Ethanal gains one oxygen atom to become ethanoic acid.

3. Ethanal gains two hydrogen atoms to become ethanoic acid.

4. Ethanal loses two hydrogen atoms to become ethanoic acid.

9. What human activity is most closely associated with ethanol poisoning?

1. binge drinking

2. competitive eating

3. drug using

4. practical joking

10. If someone is in danger of ethanol poisoning, what step should be taken to reduce the chance of death?

1. keep them awake

2. call 911 for emergency help

3. have them take a cold bath or shower

4. turn them on their side and let them sleep it off


Pre/Post Test – Teacher Answer Key
1. What is the common name for ethanoic acid?

1. acetic acid

2. ascorbic acid

3. lactic acid

4. salicylic acid
2. What is the IUPAC name of the compound that has the condensed structural formula H2CO?

1. methanal

2. methanol

3. hydrogen carbon (II) oxide

4. dihydrogen carbon monoxide
3. Which compound has chemical properties most similar to the chemical properties of ethanoic acid?

1. C2H5OH

2. C2H5OC2H5

3. C3H7COOH

4. C2H5COOC2H5
4. Given the balanced equation for the mild oxidation of CH3OH :
2 CH3OH + O22 H2O + 2 HCHO
What is the functional group of the organic product produced?

1. acid


2. alcohol

3. aldehyde

4. ketone
5. When considering toxic substances, LD50 is a term that often appears. What do the letters, “LD” represent in the term LD50?

1. legally dead

2. learning disabled

3. lethal dose

4. limited degree
6. Given the structural formulas of four organic compounds

Which pair contains an alcohol and an acid?

1. a and b

2. a and c

3. b and d

4. c and d

7. When applied to measurements, what is the meaning of the statement, “Your precision is good but not your accuracy?”

1. Your values are close to the true value and are close to each other.

2. Your values are close to the true value but are not close to each other.

3. Your values are not close to the true value but are close to each other.

4. Your values are not close to the true value and are not close to each other.

8. When ethanal is converted into ethanoic acid, which statement describes what happens in the reaction?

1. Ethanal loses one oxygen atom to become ethanoic acid.

2. Ethanal gains one oxygen atom to become ethanoic acid.

3. Ethanal gains two hydrogen atoms to become ethanoic acid.

4. Ethanal loses two hydrogen atoms to become ethanoic acid.

9. What human activity is most closely associated with ethanol poisoning?

1. binge drinking

2. competitive eating

3. drug using

4. practical joking
10. If someone is in danger of ethanol poisoning, what step should be taken to reduce the chance of death?

1. keep them awake

2. call 911 for emergency help

3. have them take a cold bath or shower



4. turn them on their side and let them sleep it off

Teacher Information
Learning Context:

  • This learning experience is designed for high school students taking a chemistry course.

  • Students should be familiar with using the Internet and have access at the school unless doing this as a directed study.

  • Students should know how to name alkanes minimally knowing the prefixes meth- and eth-.


Overall Purpose:
  • The overall purpose of the learning experience is to learn more about alcohols, aldehydes and organic acids as well as to become aware of alcohol poisoning and the limitations of a Breathalyzer.




Student Learning Objectives:

  • Students will be able to recognize important functional groups, in particular, alcohols, aldehydes and organic acids.

  • Students will be able to name simple aldehydes, organic acids and monohydroxy alcohols using IUPAC nomenclature or common names.

  • Students will be able to identify organic oxidation reactions that either add oxygen or remove hydrogen.

  • Students will know the mild oxidation of an aldehyde produces an organic acid.

  • Students will know the mild oxidation of methanol or ethanol produces an aldehyde as the organic product.

  • Students will be able to classify an organic compound based on its structural or condensed structural formula.

  • Students will be able to draw a structural formula with the functional group(s) on a straight chain hydrocarbon backbone, when given the IUPAC name for the compound.

  • Students will be able to create and use molecular models of organic molecules to illustrate their shape and simulate mild oxidation reactions of alcohols and aldehydes.

  • Students will be able to create and use molecular models of organic molecules to show they differ in their structures.

  • Students will be able to define and use the terms precision and accuracy when applied to a Breathalyzer.

  • Students will be able to define toxic and explain the term LD50.

  • Students will be able to identify what to do if someone shows signs of alcohol poisoning.



Procedure:
Classroom Timeline:

Day 1


Part 1

15 minutes

Read article




Part 2

30 minutes

Web Quest

Day 2




45 minutes

Molecular modeling activity

Day 3




45 minutes

Prepare for presentation

Day 4




45 minutes

Presentations



Day 1 - Part 1: Read Article (15 minutes)

The students should be given a copy of the article on the next page, “Bizarre Fatality in the Suburbs.” The article is fiction but it is a compilation based on real cases.

Allow them to read the article and when everyone finishes ask students to think about the article they have just read. They are then paired up with a classmate to share their opinion about the article. Some students may then briefly share their thoughts with the whole class.



Bizarre Fatality in the Suburbs

By Joshua Good


Jason Drake, 17, a senior at Borders High School, died an unusual death Friday night. Police sources stated Jason had attended a party with friends and classmates at the home of Thomas and Julie Contrary who were out of town.

The party started around 9:00 PM but young Drake did not arrive until approximately one hour later. The teenagers reported drinking a mixture of concentrated juice, vodka, and beer placed in a punch bowl, a drink called “jungle-juice” by the teenagers. After the first bowl of the beverage was consumed Will Contrary, 16, son of Thomas and Julie, went to get more vodka for the second batch. It was about this time that Jason Drake arrived.

Will’s father admitted he would illegally bring vodka back from Canada. He would fill empty bottles of windshield-wash with vodka and then add blue food coloring to make it seem like windshield-washer fluid to avoid the tariff for importing alcohol that is imposed at the border. Will took what he thought was one of his father’s illegal imports from the basement. Unfortunately, the bottle that he took was in fact windshield-washer fluid that contained methyl alcohol as the main ingredient. Will Contrary then proceeded to make another bowl of the drink using the bottle of windshield-washer fluid.

Students at the party said that Jason had then tried to “catch up” by drinking two large glasses of the punch immediately. Jason seemed to be having no difficulties but sometime later he passed out. Two of his friends decided that since this was a fairly common occurrence at this sort of party the best thing to do would be to take him across the street to his house and put him to bed.

Jason’s friend and fellow senior Mark Townsend, 17, who was one of those who carried him, had this to say, “Well, he just

passed out. I mean, lots of people pass out at

parties. Since his house was right across the street and no one was home we didn’t think there’d be a problem leaving him there. We turned him on his side and made sure he had a bucket and everything. We didn’t think there was anything wrong. It’s just one of those things, you know? We thought we were helping him out by getting him home so no one knew he’d been at a party.”

The next evening when Jason’s mother, who had recently returned from a business trip, decided to awaken him for dinner, found that she could not rouse him. She called 911 and he was rushed to St. Joseph’s Hospital. He was declared dead upon arrival. Toxicity tests later showed that he had died of methanol poisoning.

The people in this tight-knit community are doing more than just talking about how to address the issue of teenage alcohol abuse. Board of Education President Dr. Herman Melville proposes a solution. He favors breathalyz­ers be used at all school functions. This is a policy adopted at a growing number of schools to deter drinking at after-school events. Dr. Melville supports a one-strike and your out, zero-tolerance policy. Students who test positive for alcohol will be ineligible for all extracurricular activities, including sports, and performances in plays or concerts, for one full year.

William Pratt, a 16-year-old junior at the school, said he would “refuse to be tested even if he did not have any alcohol as a matter of privacy.” In an attempt to be less disruptive, officials at the school said they would “only use alcohol testing on students they suspect have been drinking.” “It really won’t change the problem; if kids want to drink they will,” says Susie Kerr, a 17-year-old senior.

According to senior Timothy Dayton, 17, each year since he can remember there has been an incident in which someone “almost” died from drinking too much. “It’s totally out of control,” said another senior, Jared Hall, 18.



Day 1 – Part 2: Web Quest (30 minutes)
Students will now do a “Web Quest” and use Internet resources to prepare for a presentation to the Board of Education. Have the students read the “Board of Education Presentation” (see following page). Students should then be given time to seek answers to questions five different questions that you assign to each pair using the matrix provided. This will ensure that each of the ten questions have been answered by several groups. Note that each group will be answering question 6 and question 10 which are deemed to be most important for all students to address.
See the teacher reference guide for suggested search words and Internet addresses.
This activity will take approximately thirty minutes although some students may require longer. You could have students finish their assigned questions for homework, but is not required so long as several pairs of students have answers to each of the questions.
Important Note: The questions are provided in three alternative formats.

  1. An open internet inquiry format where students search for their own sites.

  2. A directed internet inquiry format where sites for student research are suggested.

  3. An inquiry format that does not require the use of computers.


Select the question format that best suits your classroom constraints and teaching goals.






Board of Education Presentation

The board of education is debating a policy to deter drinking at after-school events. They want to randomly test students who enter school dances, night football games, school plays and any after-hour event with Breathalyzers.

The president of the Board of Education believes this will address the widespread problem of student drinking. The chemistry class has been asked to prepare a presentation on the “Chemistry of Alcohol, Breathalyzers and School Policy to Deter Drinking” for the next Board of Education meeting.

The class presentation should answer the ten questions that follow, express their opinion on the use of Breathalyzers, and provide a rationale for their opinion. You should suggest actions the Board of Education should take to curb the student-drinking problem.


Research the answers to the questions for your presentation using Internet resources, working in pairs on assigned questions. Be sure to include Internet references with your answers. If you have trouble finding the answer to a question, raise your hand and ask your teacher for assistance. If you complete all of your assigned questions, you can continue to work on the rest of the ten questions.


Questions for Internet Inquiry:


  1. (a) Can someone die of water intoxication (drinking too much water)?

    1. Find an example of someone who died due to water intoxication.



  1. What makes something toxic?




  1. Scientists often report toxicity using the term LD50. What is LD50?




  1. How toxic is methanol (methyl alcohol)?




  1. How toxic is ethanol (ethyl alcohol)?




  1. Methanol and ethanol are both metabolized into an aldehyde and then an organic acid. Why then is methanol more toxic than ethanol?




  1. Why does the treatment for methanol poisoning involve giving the patient ethanol?




  1. If someone is in danger of ethanol poisoning, what steps should be taken to reduce the chance of death?




  1. (a) What is a Breathalyzer?

    1. How does a Breathalyzer work?



  1. Reliability is reproducibility of multiple measurements free from random error which in this case would mean if the test were repeated several times with the same subject, would the readings be the same?

Accuracy is how close a measurement comes to the true value, which in this case is the blood alcohol concentration (BAC).


How reliable is a Breathalyzer? How accurate is a Breathalyzer?

Please answer the following questions in the order listed. If you finish early, then look up the answers to some of the other ten questions. Be sure to not only answer the question, but to include the web site where you found the answer.

Ask you teacher if you are having trouble with any particular question.

Student Names Assigned Questions

___________________________________________ Pair #1: 1, 2, 3, 6, 10

___________________________________________ Pair #2: 4, 5, 6, 7, 10

___________________________________________ Pair #3: 6, 8, 9, 10, 1

___________________________________________ Pair #4: 10, 9, 8, 7, 6

___________________________________________ Pair #5: 1, 2, 3, 6, 10

___________________________________________ Pair #6: 4, 5, 6, 7, 10

___________________________________________ Pair #7: 6, 8, 9, 10, 1

___________________________________________ Pair #8: 10, 9, 8, 7, 6

___________________________________________ Pair #9: 1, 2, 3, 6, 10

___________________________________________ Pair #10: 4, 5, 6, 7, 10

___________________________________________ Pair #11: 6, 8, 9, 10, 1

___________________________________________ Pair #12: 10, 9, 8, 7, 6

___________________________________________ Pair #13: 1, 2, 3, 6, 10

___________________________________________ Pair #14: 10, 9, 8, 7, 6


Questions for Directed Internet Inquiry:

1. (a) Can someone die of water intoxication (drinking too much water)?

Suggested web sites:

http://chemistry.about.com/cs/5/f/blwaterintox.htm

http://www.fbnewsleader.com/articles/2006/07/29/sports/03greg.txt

Search Tip: use quotation marks and search “water intoxication”


(b) Find an example of someone who died due to water intoxication.

Suggested web sites:



http://www.npr.org/templates/story/story.php?storyId=5012154

Search Tip: use quotation marks and search “water intoxication” and death

2. What makes something toxic?

Suggested web sites:



http://www.oceanservice.noaa.gov/education/kits/pollution/lessons/pollution_seeds.pdf

http://en.wikipedia.org/wiki/Toxicology

Search Tip: use toxicology and/or poison in your search string


3. Scientists often report toxicity using the term LD50. What is LD50?

Suggested web sites:



http://en.wikipedia.org/wiki/LD50

Search Tip: use LD50


4. How toxic is methanol (methyl alcohol)?

Suggested web sites:



http://www.nlm.nih.gov/medlineplus/ency/article/002680.htm

http://www.flinnsci.com/search_MSDS.asp

Search Tip: using some combination of search words that include LD50 or toxicity and methanol or methyl alcohol


5. How toxic is ethanol (ethyl alcohol)?

Suggested web sites:


http://www.flinnsci.com/search_MSDS.asp

Search Tip: using some combination of search words that include LD50 or toxicity and ethanol or ethyl alcohol

6. Methanol and ethanol are both metabolized into an aldehyde and then an organic acid. Why then is methanol more toxic than ethanol?

Suggested web sites:



http://en.wikipedia.org/wiki/Alcohol - Toxicity

http://chemmovies.unl.edu/chem_source_pdf/ChemSource.html (Organic)

Search Tip: use the words alcohol metabolism


7. Why does the treatment for methanol poisoning involve giving the patient ethanol?

Suggested web sites:



http://en.wikipedia.org/wiki/Alcohol - Toxicity http://www.emedicine.com/NEURO/topic217.htm

Search Tip: treatment methanol poisoning


8. If someone is in danger of ethanol poisoning, what steps should be taken to reduce the chance of death?

Suggested web sites:



http://www.collegedrinkingprevention.gov/media/NIAAA_Grad_Flyer_NEW.pdf

http://www.collegedrinkingprevention.gov/OtherAlcoholInformation/factsAboutAlcoholPoisoning.aspx

Search Tip: search "alcohol poisoning"


9. (a) What is a Breathalyzer?

Suggested web sites:



http://en.wikipedia.org/wiki/Breathalyzer

Search Tip: Breathalyzer


(b) How does a Breathalyzer work?

Suggested web sites:



http://science.howstuffworks.com/breathalyzer2.htm

http://science.howstuffworks.com/breathalyzer3.htm

Search Tip: Breathalyzer works

10. Reliability is reproducibility of multiple measurements free from random error which in this case would mean if the test were repeated several times with the same subject, would the readings be the same?

Accuracy is how close a measurement comes to the true value which in this case is the blood alcohol concentration (BAC). How reliable is a Breathalyzer? How accurate is a Breathalyzer?

Suggested web sites:

http://www.ncdd.com/dsp_articledetails.cfm?article=2

http://www.bookrags.com/other/drugs/breathalyzer-dat-01.html

Search Tip: Breathalyzer reliability





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