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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3270

Consider only the mono-enol forms of the compound shown, in which one carbonyl group is converted into and the other stays as C=O. Counting E and Z isomers separately, how many distinct mono-enol forms are there?

  1. A2
  2. B3
  3. C4
  4. D5

Answer: B

The compound shown is pentane-2,4-dione. Enolisation of a carbonyl toward a terminal CH gives a terminal enol , with no E/Z isomerism. Enolisation toward the central CH gives , which exists as E and Z isomers. Because the two carbonyls are equivalent, the total is , confirmed by RDKit enumeration.
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