Problem

Azulene is a deep-blue hydrocarbon with resonance energy of 205 kJ mol (49 kcal mol). Az...

Azulene is a deep-blue hydrocarbon with resonance energy of 205 kJ mol (49 kcal mol). Azulene has ten pi electrons, so it might be considered as one large aromatic ring. Its electrostatic potential map shows one ring to be highly electron-rich (red) and the other to be electron-poor (blue). The dipole moment is unusually large (1.0 D) for a hydrocarbon. Show how this charge separation might arise.

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