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Project-Based Labs
Green Oxidation
Introduction
Your company, Acme Oxidation, has been cited and fined by the Environmental Protection
Agency (EPA) for being in non-compliance with regulations concerning the release of
chromium(VI) oxide, a known toxic substance, into the sewer system. To save your company,
you must find a green chemistry approach to your business of oxidizing alcohols. In the past,
oxidation of alcohols has been performed using chromium or some other heavy metal in a high
oxidation state. You have been notified that, in the future, you must either use some more
environmentally benign oxidizing agent, or possibly find a way to recycle the metallic oxidizing
agent.
Preliminary research has given rise to some promising leads. It is your job to figure out
which alternative oxidation method is the most effective, environmentally friendly, and
economically viable.
For your initial trials, you will use
OH
benzhydrol as your starting alcohol. This is its
C
structure. For additional information about
H
alcohols, see the resource section that follows.
The oxidants available to you are Clorox
household bleach, which contains sodium hypochlorite, and a material called Magtrieve, which
contain CrO2. Magtrieve is used on the surface of audiocassette tapes. The bleach you can use
as is and you will be supplied with Magtrieve as a powder.
Project Tasks
Some of these tasks will be accomplished experimentally and some by library or web-based
research in appropriate resources.
1. Investigate each oxidizing agent to find which works best for benzhydrol oxidation.
2. Identify the byproducts that remain after reactions of the oxidants.
3. Decide which of these oxidants is the most environmentally friendly.
4. Consider which oxidant will be the most cost effective for Acme Oxidations.
5. Determine if either oxidant is recyclable.
6. Determine if results observed with benzhydrol can be reproduced with other alcohols.
7. Optional: Use thin-layer chromatography to follow the course of the reaction.
8. Optional: Use infrared (IR) analysis to determine if the alcohol has been oxidized.
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Resources Available
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4.
Reports
1. Planning sheets are to be completed as directed by your instructor.
2. The final report for this project should follow the basic guidelines given previously.
Be sure to include:
a. observations and other results from all group experiments.
b. references for all information from the web or other resources
c. comparison and contrast of the two possible oxidation methods, and their
advantages over the original method.
3. Be sure you support your report recommendations with data from the various aspects of
the project, including cost, safety, environmental impact, and effectiveness in oxidizing
the alcohol.
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Resource: Alcohols
All alcohols contain a covalently bonded OH group. They are commonly classified
according to their structures into three types; primary, secondary, and tertiary alcohols.
Primary Alcohol
Secondary Alcohol
Tertiary Alcohol
H
R C OH
H
H
R C OH
R'
R''
R C OH
R'
Primary alcohols are generall oxidized to aldehydes under the conditions of this project; they
may be oxidized all the way to carboxylic acids by stronger conditions. Secondary alcohols are
typically oxidized to ketones. Tertiary alcohols cannot be oxidized under the conditions in this
project. There must be at least one hydrogen on the carbon containing the OH group for the
oxidation to be effective using either Clorox or Magtrieve.
Resource: Oxidation Using Clorox
This equation shows the general process for the oxidation of a secondary alcohol using
sodium hypochlorite.
R2CHOH + NaOCl R2CO + NaCl + H2O
To carry out this oxidation, start with 1 gram of alsohol and dissolve it in 1 M acetic acid.
From the stated concentration on the label, calculate how much bleach you will need to oxidize
the alcohol sample. Add bleach drop by drop over a 45-minute period.
Use some of the product and use TLC to check whether or not the reaction has taken place.
When all of the alcohol appears to have reacted, or after 2 hours, add ice water to dilute the
reaction mixture. Make the acetic acid more water soluble by adding solid sodium carbonate or
sodium bicarbonate until there is no additional effervescence.
See if your product crystallizes. If so, filter, dry and recrystallize the product. If your product
will not crystallize, extract the product with three portions of ether, dry the ether extracts, filter
and evaporate the solvent with a gentle stream of air of nitrogen gas. Then recrystallize the
product.
Characterize the isolated product as indicated by your instructor.
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Project-Based Labs
1. Look on the web or in another source to find a definition of green chemistry. Rephrase the
definition in your own words.
2.
3. What is the chemical formula for benzhydrol? What type of alcohol is benzhydrol? What are
its properties? Report any references used to help answer these questions.
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4.
Which functional group is changed by the procedures that you will carry out in lab? Draw
out each reaction scheme using structural formulas for each procedure. Identify the new
functional group produced by the oxidation.
5. If fresh household Clorox is 5.25% by weight NaOCl, what volume of bleach should you use
to oxidize 1 g of alcohol? Show your work.
6. Exactly which species in bleach is the oxidizing agent? How do you know?
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Group Name___________________
1. Describe how you obtained and identified your product from the bleach oxidation.
2. Describe how you obtained and identified your product from the Magtrieve oxidation.
3. Compare the two methods for ease of use, purity of product, and percentage recovery.
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4. What property of Magtrieve makes its separation from your reaction mixture quick and easy?
5. Magtrieve was recycled by heating it in an oven at 250 C. What do you think happens to the
Magtrieve during this process? Explain your reasoning.
6. What additional information will be needed before next week, when your boss at Acme
Oxidation wants a draft of your report presented at the Board of Directors meeting?
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Group Name___________________
1. Describe the results of any additional experimentation that your group carried out today in
lab.
2. Which method of oxidation is the greenest? Define your terms and decide how you will
communicate this information to your boss.
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3. Which method of oxidation is the most economical? Give references used to gather this
information.
4. What additional points will you include in your final report to the boss? How will you
organize your report? Communicate the criteria by which you are judging the best
oxidizing agent for this company to use. Outline your groups ideas.
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