Chapter 14, Problem 14.56P

Interpretation Introduction

Interpretation:

It is to be explained why bromobenzene is insoluble in water but $\text{7-bromocyclohepta-1, 3, 5-triene}$ is water-soluble.

Concept introduction:

The major intermolecular interaction between the molecules of water is hydrogen bonding. Hydrogen bonding is a form of dipole-dipole interaction but with substantially higher energy than the usual dipole-dipole interactions.

For a compound to be soluble in water, the type of intermolecular interactions between its molecules must be similar to that in water. It must exhibit substantial dipole-dipole interactions or a capability to form hydrogen bonds with water molecules.

A polar solvent can induce heterolysis of a carbon-halogen bond, accompanied by solvation of the ions.