Chlorobenzenc, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl},\) is a key
intermediate in the manufacture of dyes and pesticides. It is made by the
chlorination of benzene, catalyzed by \(\mathrm{FeCl}_{3}\), in this series of
steps:
(1) \(\mathrm{Cl}_{2}+\mathrm{FeCl}_{3} \rightleftharpoons
\mathrm{FeCl}_{5}\left(\right.\) or \(\left.\mathrm{Cl}^{+}
\mathrm{FeCl}_{4}^{-}\right)\)
(2) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{Cl}^{+} \mathrm{FeCl}_{4}^{-}
\rightleftharpoons \mathrm{C}_{6} \mathrm{H}_{6}
\mathrm{Cl}^{+}+\mathrm{FeCl}_{4}^{-}\)
(3) \(\mathrm{C}_{6} \mathrm{H}_{6} \mathrm{Cl}^{+} \rightleftharpoons
\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}+\mathrm{H}^{+}\)
(4) \(\mathrm{H}^{+}+\mathrm{FeCl}_{4}^{-} \rightleftharpoons
\mathrm{HCl}+\mathrm{FeCl}_{3}\)
(a) Which of the step(s) is (are) Lewis acid-base reactions?
(b) Identify the Lewis acids and bases in each of those steps.