678PHENOLSIt is also possible that the elimination stage of the reaction proceeds as follows: 24.5The text states that the hydrolysis of chlorobenzene in base follows an elimination–additionmechanism.24.6(b)The reaction is Friedel–Crafts alkylation. Proton transfer from sulfuric acid to 2-methyl-propene givestert-butyl cation. Because the position para to the hydroxyl substituentalready bears a bromine, the tert-butyl cation attacks the ring at the position ortho to thehydroxyl.(c)Acidifcation of sodium nitrite produces nitrous acid, which nitrosates the strongly activatedaromatic ring of phenols.
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