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What happens when 2-hydroxycyclohexan-1-one (an alpha hydroxyketone) reacts with aqueous $\ce{KOH}$?

2-hydroxycyclohexan-1-one

I tried something like Favorskii rearrangement, but it's wrong because OH isn't a good enough leaving group.

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    $\begingroup$ Deprotonation, ring expansion to CSID:9972, chemspider.com/Chemical-Structure.9972.html (accessed 15:03, Jul 4, 2018)? Maybe? $\endgroup$ – Martin - マーチン Jul 4 '18 at 14:04
  • $\begingroup$ Is that all? Are you sure? $\endgroup$ – arya_stark Jul 4 '18 at 17:25
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    $\begingroup$ Oh no, not sure at all; hence a comment, hence question marks and the word maybe. There was no sarcasm meant by any of this, just offering the first thing that came to my mind until someone more versed in synthetic chemistry comes along. $\endgroup$ – Martin - マーチン Jul 4 '18 at 17:29
  • $\begingroup$ Who says anything happens? Aq KOH isn't really strong enough to deprotonate the alcohol. $\endgroup$ – Waylander Jul 5 '18 at 10:32
  • $\begingroup$ Well alpha hydroxy ketones in the presence of a Base or acid will tautomerise and thus have their OH converted to aldehyde /ketone and vice versa. Though I am not sure how that would help since in this case you get the same compound anyways $\endgroup$ – The East Wind Jul 9 '18 at 19:07

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