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Dolbier HW Solutions 588 - 682 PHENOLS 24.13(a The reaction...

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24.13 ( a ) The reaction is an acid base reaction. Phenol is the acid; sodium hydroxide is the base. ( b ) Sodium phenoxide reacts with ethyl bromide to yield ethyl phenyl ether in a Williamson reaction. Phenoxide ion acts as a nucleophile. ( c ) p -Toluenesulfonate esters behave much like alkyl halides in nucleophilic substitution reac- tions. Phenoxide ion displaces p -toluenesulfonate from the primary carbon. ( d ) Carboxylic acid anhydrides react with phenoxide anions to yield aryl esters. ( e ) Acyl chlorides convert phenols to aryl esters. ( f ) Phenols react as nucleophiles toward epoxides. CH 3 OH m -Cresol Ethylene oxide H 2 C CH 2 O 2-(3-Methylphenoxy)ethanol H 3 C OCH 2 CH 2 OH OH OC HCl CH 3 CH 3 CCl O O o -Cresol
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