91Ó°ÊÓ

Taking advantage of their large differences in \(\mathrm{pK}_{\mathrm{a}}\) values, describe how a mixture of phenol and benzoic acid in diethyl ether solution could be separated. How could a mixture of phenol and cyclohexanol in diethyl ether solution be separated?

Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or \(p\) -hydroxybenzaldehyde (b) \(m\) -Cyanophenol or \(p\) -cyanophenol (c) o-Fluorophenol or \(p\) -fluorophenol

Write a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) \(+\) ethyl bromide (c) Product of part (a) \(+\) butyl \(p\) -toluenesulfonate (d) Product of part (a) \(+\) acetic anhydride (e) \(o\) -Cresol + benzoyl chloride (f) \(m\) -Cresol \(+\) ethylene oxide (g) 2,6-Dichlorophenol + bromine (h) \(p\) -Cresol \(+\) excess aqueous bromine (i) Isopropyl phenyl ether \(+\) excess hydrogen bromide \(+\) heat

Treatment of 3,5 -dimethylphenol with dilute nitric acid, followed by steam distillation of the reaction mixture, gave a compound \(\mathrm{A}\left(\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{NO}_{3}, \mathrm{mp} 66^{\circ} \mathrm{C}\right)\) in \(36 \%\) yield. The nonvolatile residue from the steam distillation gave a compound \(\mathrm{B}\left(\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{NO}_{3}, \mathrm{mp} 108^{\circ} \mathrm{C}\right)\) in \(25 \%\) yield on extraction with chloroform. Identify compounds \(\mathrm{A}\) and \(\mathrm{B}\).