Chapter 14, Problem 14.55P

Interpretation Introduction

Interpretation:

The difference in the calculated dipole moments of the two compounds J and K is to be explained.

Concept introduction:

In an unsaturated ring with an incomplete conjugation or a saturated ring with a suitable number of double-bonded substituents, it is possible for the ring to gain aromatic stabilization through a change in hybridization and/or through resonance. In this case, the extra stability gain drives such transformations, and the ring behaves like an aromatic compound.

If this process involves a charge separation, the molecule may gain polarity even if it is not inherently polar.

Dipole moment is the product of the charge and the distance separating the opposite charges. Generally, the charges in such structures are just unit charges, so the dipole moment primarily depends on their separation. Larger the distance between the centers of the positive and negative charge, larger the dipole moment.