How Would The Stability Of The Phenonium Ion Change?

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Draw resonance structures showing all the positions at which the positive charge is delocalized on the aromatic ring in the phenonium ion. If a methoxy group (-OCH3) or a nitro group (–NO2) were substituted in the 4-position on the aromatic ring, how would the stability of the phenonium ion change? Compare methoxy substituted, nitro substituted and unsubstituted, and order them by increasing stability. Explain your answer thoroughly.

2) Benzopinacol and benzopinacolone have nearly identical boiling points. How would you distinguish the two using only techniques that we have used in the laboratory?
To distinguish between benzopinacol and benzopinacolone I would use the IR spectrum because benzopinacol has a strong IR peak between

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