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JEE Advanced levelSingle correct optionDifficulty 3 of 3g2202

In non-polar hexane, the dominant species of pentane-2,4-dione is

  1. A(Z)-4-hydroxypent-3-en-2-one, the chelated cis-enol
  2. Bpentane-2,4-dione, the diketo form
  3. C(E)-4-hydroxypent-3-en-2-one, the trans-enol
  4. D4-hydroxypent-4-en-2-one, the terminal enol

Answer: A

In non-polar media the enol with an intramolecular hydrogen bond (six-membered chelate) is strongly favoured and amounts to about 97 percent. Only the Z (cis) enol can form the chelate. The E enol cannot, and the terminal enol lacks conjugation, so both are minor.
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