Dolbier HW Solutions 595

Dolbier HW Solutions 595 - 689 PHENOLS(i Chlorination with...

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( i ) Chlorination with excess chlorine occurs at all available positions that are ortho and para to the hydroxyl group. ( j ) Amines react with esters to give amides. In the case of a phenyl ester, phenol is the leaving group. ( k ) Aryl diazonium salts attack electron-rich aromatic rings, such as those of phenols, to give the products of electrophilic aromatic substitution. 24.18 In the f rst step p -nitrophenol is alkylated on its phenolic oxygen with ethyl bromide. Reduction of the nitro group gives the corresponding arylamine. Treatment of p -ethoxyaniline with acetic anhydride gives phenacetin. 1 p -Ethoxyaniline OCH 2 CH 3 H 2 N Acetic anhydride CH 3 COCCH 3 O O p -Ethoxyacetanilide (phenacetin) OCH 2 CH 3 CH 3 CNH O OCH 2 CH
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