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JEE Advanced levelSingle correct optionDifficulty 3 of 3co201

Ethyl 3-oxobutanoate is treated with one equivalent of sodium ethoxide and then one equivalent of bromoethane; the product is heated with dilute aqueous , then acidified and warmed. The final organic product is

  1. Apentan-2-one
  2. Bbutan-2-one
  3. Cpentan-3-one
  4. D2-ethyl-3-oxobutanoic acid

Answer: A

Alkylation at the active methylene gives ethyl 2-ethyl-3-oxobutanoate. Hydrolysis gives 2-ethyl-3-oxobutanoic acid, a beta-keto acid that loses on warming: . The product is pentan-2-one.
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