Why is the dipole moment of the C-Cl bond in chlorobenzene lower than that of cyclohexyl chloride?
1 Answer
There are a couple of factors that contribute to the lower dipole moment for the
Take a look at the two molecules, chlorobenzene and cyclohexyl chloride
Notice that the chlorine atoms are attached to carbon atoms that have a different orbital hybridization. In chlorobenzene, the carbon to which chlorine is attached is
That has an impact on dipole moment because the greater the s character of the hybrid orbital, the more electronegative that carbon atom will be. The
Another important factor is the fact that chlorobenzene is resonance-stabilized, which means that the lone pairs of electrons on the chlorine atom will be delocalized on the benzene ring
.
As a result, the
By comparison, the
These two factors are what determine the dipole moment for the