A resonance structure will be insignificant if it has carbon atoms with opposite charges (C- and C ). Azulene represents an exception to this rule, because some resonance structures (with C- and C ) exhibit aromatic stabilization. Draw a resonance structure of azulene with formal charges that best explains the aromatic stabilization. Include lone pairs in your answer.

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Explanation:

Resonance is a way of describing delocalized electrons within certain molecules or polyatomic ions where the bonding cannot be expressed by a single Lewis formula. A molecule or ion with such delocalized electrons is represented by several resonance structures(Chemlibretexts).

Azulene, an isomer of naphthalene is an aromatic hydrocarbon whose structure has been shown in the image attached to this answer. Usually, charge separation decreases the stability of a resonance structure.

As a result of this charge separation in azulene, Naphthalene is more stable than azulene.

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