682 PHENOLS 24.13(a)The reaction is an acid-base reaction. Phenol is the acid; sodium hydroxide is the base. (ONa+ Ho Pheno Sodium Sodium phenoxide (weaker acid) (b) Sodium phenoxide reacts with ethyl bromide to yield ethyl phenyl ether in a Williamson reaction. Phenoxide ion acts as a nucleophile C6H ONa CH CH, Br CHOCH CH NaBr Sodium Ethyl phenyl ether Sodi (c) p-Toluenesulfonate esters behave much like alkyl halides in nucleophilic substitution reac tions. Phenoxide ion displaces p-toluenesulfonate from the primary carbor H_ ONa CH3CH,CH, CH,O C6H-OCH, CH, CH, CH3 NaoS SycH Sodium Butyl p-toluenesulfonate Butyl phenyl ether Sodium p-toluenesulfonate (d) Carboxylic acid anhydrides react with phenoxide anions to yield aryl esters CH,ONa CH, COCCH C.HOCCH,+CH,CONa Sodium Acetic anhydride Phenyl acetate Sodium (e) Acyl chlorides convert phenols to aryl esters CC t HCl o-cresol Benzoyl chloride 2-Methylphenyl benzoate Hydrogen (f) Phenols react as nucleophiles toward epoxides. CH H, C +H2C—CH DCH,CH,OH m-cresol 2-(3-Methylphenoxy )ethanol Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website24.13 (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. CH3 OH  m-Cresol Ethylene oxide H2C CH2 O 2-(3-Methylphenoxy)ethanol H3C OCH2CH2OH OH OC HCl CH3 CH3 CCl   O O o-Cresol Benzoyl chloride 2-Methylphenyl benzoate Hydrogen chloride C6H5ONa C   CH3COCCH3 6H5OCCH3 CH3CONa Sodium phenoxide Acetic anhydride Phenyl acetate Sodium acetate O O O O C6H5ONa C   CH3CH2CH2CH2OS 6H5OCH2CH2CH2CH3 NaOS Sodium phenoxide Butyl p-toluenesulfonate Sodium Butyl phenyl ether p-toluenesulfonate O O O O CH3 CH3 C CH3CH2Br 6H5ONa C   6H5OCH2CH3 NaBr Sodium phenoxide Sodium bromide Ethyl bromide Ethyl phenyl ether OH   NaOH ONa H2O Phenol (stronger acid) Water (weaker acid) Sodium hydroxide (stronger base) Sodium phenoxide (weaker base) 682 PHENOLS Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website