Chapter 12, Problem 2E

When another atom or group of atoms is substituted for one of the hydrogen atoms in benzene, ${\text{C}}_2{\text{H}}_2$ , the boiling point changes. Explain the order of the following boiling points: ${\text{C}}_2{\text{H}}_2,80°{\text{C;C}}_{\text{2}}{\text{H}}_{\text{2}}{\text{Cl, 132°C;C}}_{\text{2}}{\text{H}}_{\text{2}}{\text{Br, 156°C;C}}_{\text{6}}{\text{H}}_{\text{6}}\text{OH, 182°C}$ .