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Why is the keto form of acetyl chloride more stable even though the enol form is stabilized by the hydrogen bonding?

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    $\begingroup$ The enol form of acetyl chloride isn't stabilized by hydrogen bonding. Can you include a picture of what you mean? $\endgroup$
    – jerepierre
    Commented Apr 4, 2015 at 4:34
  • $\begingroup$ The enol form is stabilised more than or comparable to ketones in phenol and 1,3 or 2,4 type diketones. $\endgroup$ Commented Apr 4, 2015 at 18:28

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The stability of keto-enol compounds depends on the solution they are present in.

Keto compounds are stabilized due to inter-molecular hydrogen bonding when present in a polar solvent (for example water).

Enol compounds are stable when present in non-polar solvents, in which intra-molecular hydrogen bonding stabilizes them.

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