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JEE Main levelSingle correct optionDifficulty 2 of 3g3239

The compound shown is treated with a base and loses one proton from carbon. Which carbanion shown is the most stable?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The compound shown is ethyl acetoacetate. Deprotonation of the central CH gives a carbanion flanked by two carbonyl groups, which delocalises the charge onto both oxygens. The CH carbanion is stabilised by only one carbonyl, and the carbanions on the ethyl group are not conjugated with any carbonyl.
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