I'm struggling to figure out the mechanism for the following reaction.
KOH/EtOH
p-benzoquinone ------------> p-dialoxybenzoquinone
R-Br
where R-Br is a primary haloalkane.
I suspect that this has something to do with the R-Br + OH- -> R-OH + Br- but I'm not sure where to go from there. I have a feeling like the bromide ion is involved but am not sure how. I tried working backwards from the p-dialkoxybenzoquinone to a likely precursor, hydroquinone, but I'm not sure where to go from there.
Many thanks.