Here is my proposed mechanism, something tells me that the intramolecular deprotonation happens after, and that this is not concerted. Is my mechanism correct?
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asked May 2, 2016 at 12:34
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2$\begingroup$ Don’t draw it concerted. It is a stepwise process; the attack of the aromatic electrons onto the electrophile first with a delocalised carbocation as intermediate followed by deprotonation and rearomatising. $\endgroup$– JanCommented May 2, 2016 at 12:58
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1 Answer
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The reactivity of acid chlorides and acid anhydrides are actually quite similar. It may be helpful for you to think of an acid anhydride like this:
When we do, the acylation reaction is almost identical to that of an acid chloride, where an acylium cation $\ce{R-C#O+}$ is generated:
The subsequent proton exchange restores aromaticity:
