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Which of the following has the highest enol content at equilibrium?

  1. Apentane-2,4-dione
  2. Bpropanone
  3. Cethanal
  4. Dethyl ethanoate

Answer: A

The enol of pentane-2,4-dione is stabilised by conjugation of with and by a strong intramolecular hydrogen bond. Simple monocarbonyl compounds such as propanone, ethanal and ethyl ethanoate have negligible enol content. So pentane-2,4-dione is highest.
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