Wintergreen from Aspirin: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? 2. Write the mechanism of the esterification reaction you did. 3. What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?
Wintergreen from Aspirin: 1. In isolating the salicylic acid, why is it important to press out as much of the water as possible? 2. Write the mechanism of the esterification reaction you did. 3. What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional group change. What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What other impurities are present in your product and how do you know?
Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter19: Alkenes From Alcohols: Cyclohexene From Cyclohexanol
Section: Chapter Questions
Problem 1Q
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
Transcribed Image Text:Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
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