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What is the major product when Benzoquinone reacts with $\ce{HBr}$ ?

My effort: I thought it would be an $\text{SN}_{1}$ mechanism, but the carbocation at either double bond wouldn't be stable.

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  • $\begingroup$ Please don't introduce Mathjax code to your question titles due to some issues $\ldots$ Unless, you're talking about cerium hydrogen bromide. $\endgroup$
    – M.A.R.
    Oct 5, 2015 at 19:25
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    $\begingroup$ First, the acid will protonate the carbonyl to give a delocalized carbocation. Where will the nucleophile ($\ce{Br^{-}}$) attack; attack at which position can lead to a stable (aromatic) product by loss of $\ce{H^{+}}$? $\endgroup$
    – ron
    Oct 6, 2015 at 2:15

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