Problem

The most stable resonance contributor for the acylium ion is one in which the positive cha...

The most stable resonance contributor for the acylium ion is one in which the positive charge is on oxygen rather than carbon; however, the addition of an acylium ion to benzene in the Friedel-Crafts reaction takes place at the carbon. Consider the structure of the cyclohexadienyl cation that would result if the addition of acylium ion took place on oxygen, and explain why this pathway is unfavorable.

 

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