Write a mechanism acetaminophen is reacted with NaOH in ethanol to produce C8H8N02 which is then...
Write a mechanism
acetaminophen is reacted with NaOH in ethanol to produce C8H8N02 which is then reacted with tert-butyl iodide . What does this produce and what is the mechanism for the entire process?
Homework Answers
when acetaminophen is reacted with naoh in ethanol,then 4-acetamidophenolate will be obtained.
When 4-acetamidophenolate is reated with tert-butyl iodide, then phenacetin will be obtained.
This reaction is Williamson synthesis reaction.
4-acetamidophenolate acts as an electrophile and attacks ethyl iodide to create phenacetin
4-acetamidophenol is converted to 4-acetamidophenolate
Ethyl iodide first converts 4-acetamidophenol to 4-acetamidophenolate (an alkoxide ion)
Second, 4-acetamidophenolate acts as a nucleophile, and attacks ethyl iodide to create phenacetin
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Write a mechanism
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