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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3274

Which statements about the compound shown are correct? Count as alpha hydrogens those on carbons directly bonded to a carbonyl carbon. Select all that apply.

  1. AIt has 6 alpha hydrogens.
  2. BIt has exactly two constitutionally different mono-enol forms.
  3. CThe quaternary ring carbon bears an acidic hydrogen.
  4. DThe CH hydrogens between the two carbonyl groups are more acidic than those at C4 and C6.

Answer: A, B, D

The compound shown is 5,5-dimethylcyclohexane-1,3-dione (dimedone). Its alpha hydrogens are 2 on C2, 2 on C4 and 2 on C6, a total of 6; those on C2 lie between both carbonyls and are the most acidic. The quaternary carbon carries two methyl groups and no hydrogen. Enolisation toward C2 or toward C4/C6 gives two constitutionally different mono-enols (RDKit confirmed 2 distinct structures).
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