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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1259

The compound shown is treated with one equivalent of base. Which hydrogens are removed, and how many resonance structures (counting the carbanion form and enolate forms with complete octets) does the conjugate base have?

  1. Athe CH2 hydrogens between the carbonyl groups; 3 structures
  2. Bthe CH2 hydrogens between the carbonyl groups; 2 structures
  3. Cthe CH3 hydrogens of the acetyl group; 2 structures
  4. Dthe OCH3 hydrogens; 1 structure

Answer: A

The compound shown is methyl acetoacetate. The CH2 hydrogens between the two carbonyls are most acidic because the carbanion is stabilised by both. Its conjugate base has the carbanion structure plus an enolate with charge on each carbonyl oxygen, so 3 structures.
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