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When the NaOH deprotonates the hydrogen off the carbon, I thought there would be a resonance structure, with the negative charge being on both the oxygen and carbon. Since the oxygen is more stable with the negative charge, wouldn't the alkalation happen at the oxygen forming an ether? This is how i had the reaction occurring:

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    $\begingroup$ In theory, both can happen. The answer as to why alkylation on carbon is preferred can be quite complex, depending on how deep you want to go: a lot of textbooks teach it as being a result of hard-soft acid-base theory, which is a convenient rationalisation but not really true. $\endgroup$ – orthocresol♦ Feb 28 '19 at 23:59
  • $\begingroup$ Also remember, stability of the final product plays a role as well. The proposed enol-ether is relatively (thermodynamically speaking) unstable than ketone product given above. $\endgroup$ – Mathew Mahindaratne Mar 1 '19 at 2:53

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