Write a stepwise mechanism for the hydrolysis of chlorobenzene under the conditions shown in Table 24.3. TABLE

Write a stepwise mechanism for the hydrolysis of chlorobenzene under the conditions shown in Table 24.3.

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TABLE 24.3 Industrial Syntheses of Phenol Reaction and comments Chemical equation Reaction of benzenesulfonic acid with sodium hydroxide This is the oldest method for the prepa ration of phenol. Benzene is sulfonated and the SO2H он 1. NaOH 300 350°c 2. H nzenesulfonic acid heated with molten sodium hydroxide. Acidification of the reaction mixture gives phenol Hydrolysis of chlorobenzene Heating chloroben- zene with aqueous sodium hydroxide at high pres- sure gives phenol after acidification Benzenesulfonic acid Phenol 1. NaOH, H20 Cl он 2.H. Chlorobenzene Phenol From cumene Almost all the phenol produced in the United States is prepared by this method. Oxi- dation of cumene takes place at the benzylic posi tion to give a hydroperoxide. On treatment with dilute sulfuric acid, this hydroperoxide is converted to phenol and acetone CH(CH32 Isopropylbenzene OOH (CHa)z 1-Methyl-1-phenylethyl droperoxide (cumene) H2O OH + (CH3)2C-O Phenol 1-Methyl-1-phenylethyl hydroperoxide Acetone