The molecules cis-dichloroethylene and transdichloroethylene shown on p. 324
can be interconverted by heating or irradiation.
(a) Starting with cis-dichloroethylene, show that rotating the
\(\mathrm{C}=\mathrm{C}\) bond by \(180^{\circ}\) will break only the pi bond but
will leave the sigma bond intact. Explain the formation of trans-
dichloroethylene from this process. (Treat the rotation as two, stepwise
\(90^{\circ}\) rotations.) (b) Account for the difference in the bond enthalpies
for the pi bond (about \(270 \mathrm{~kJ} / \mathrm{mol}\) ) and the sigma bond
(about \(350 \mathrm{~kJ} / \mathrm{mol}\) ). (c) Calculate the longest
wavelength of light needed to bring about this conversion.