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Which hydrogens of the compound shown are the most acidic?

  1. Athe CH3 hydrogens
  2. Bthe CH2 hydrogens between the two C=O groups
  3. Call hydrogens are equally acidic
  4. Dnone of them, since there is no O-H

Answer: B

The compound is pentane-2,4-dione (acetylacetone). Loss of a CH2 proton gives an enolate stabilised over both carbonyls (pKa about 9). The terminal CH3 hydrogens (pKa about 20) give an enolate delocalised over only one carbonyl.
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