Another method for the above reaction starts with 4-aminophenol hydrochloride (the conjugate acid of 4-aminophenol). The treatment of this the hydrochloride salt with sodium ethanoate (acetate) buffer produces 4-aminophenol which is then able to react with ethanoic anhydride as per our method. i. Why is 4-aminophenol hydrochloride not suitable for direct reaction with ethanoic anhydride? ii. Draw a mechanism (i.e. curly arrows) showing the deprotonation of 4-aminophenol hydrochloride by sodium ethanoate to form 4-aminophenol (the free base).
Another method for the above reaction starts with 4-aminophenol hydrochloride (the conjugate acid of 4-aminophenol). The treatment of this the hydrochloride salt with sodium ethanoate (acetate) buffer produces 4-aminophenol which is then able to react with ethanoic anhydride as per our method. i. Why is 4-aminophenol hydrochloride not suitable for direct reaction with ethanoic anhydride? ii. Draw a mechanism (i.e. curly arrows) showing the deprotonation of 4-aminophenol hydrochloride by sodium ethanoate to form 4-aminophenol (the free base).
Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter45: Synthesis And Bioassay Of Sulfanilamide And Derivatives
Section: Chapter Questions
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2) Another method for the above reaction starts with 4-aminophenol hydrochloride (the conjugate acid of 4-aminophenol). The treatment of this the hydrochloride salt with sodium ethanoate (acetate) buffer produces 4-aminophenol which is then able to react with ethanoic anhydride as per our method.
i. Why is 4-aminophenol hydrochloride not suitable for direct reaction with ethanoic anhydride?
ii. Draw a mechanism (i.e. curly arrows) showing the deprotonation of 4-aminophenol hydrochloride by sodium ethanoate to form 4-aminophenol (the free base).
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