Organic compounds with structures based on benzene, \(\mathrm{C}_{6}
\mathrm{H}_{6},\) can be formed by substituting an atom or a group of atoms for
one of the hydrogens. Such substituted benzenes have their own properties,
different from benzene and from each other. Explain the order of experimental
boiling points for these four compounds.
(a) \(\mathrm{C}_{6} \mathrm{H}_{6}\left(80{ }^{\circ} \mathrm{C}\right)\)
(b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\left(131{ }^{\circ}
\mathrm{C}\right)\)
(c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}\left(156^{\circ}
\mathrm{C}\right)\)
(d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\left(182{ }^{\circ}
\mathrm{C}\right)\)