Question

3. We have described how acyl chloride compounds (RC=OCI) can, with the assistance of a Lewis acid catalyst, act as electrophiles in electrophilic aromatic substitution reactions. Like Lewis acids, protonic acids also can enhance the electrophilicity of carbonyl carbons. One equivalent of acetone will react with two equivalents of phenol to form the now notorious compound bisphenol A. The net reaction is indicated here. CHO OH H2SO4 OH HO НАС CH CH, bisphenol A phenol acetone (Note that 2 equivalents of phenol react with one equivalent of acetone to form one bisphenol A.) Indicate a mechanism for the preparation of bisphenol A from phenol and acetone. Note the reaction stoichiometry: two phenol molecules are needed to produce each bisphenol A molecule. Show how the sulfuric acid catalyst makes the carbonyl compound more electrophilic.