Phenacetin, a substance formerly used in over-the-counter headache remedies, has the

Chapter 24, Problem 24

(choose chapter or problem)

Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula \(\mathrm{C}_{10} \mathrm{H}_{13} \mathrm{NO}_{2}\). Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, \(\mathrm{C}_{8} \mathrm{H}_{11} \mathrm{NO}\), whose

\({ }^{1} \mathrm{H} \mathrm{NMR}\) spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, \(\mathrm{C}_{6} \mathrm{H}_{7} \mathrm{NO}\). What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?

Equation Transcription:

Text Transcription:

C_10H_13NO_2

C_8H_11NO

1H NMR

C_6H_7NO

\delta