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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3co162

Ethyl 3-oxobutanoate, , is treated with different reducing agents under the stated conditions. Which statements are correct?

  1. A in ethanol at 0 gives ethyl 3-hydroxybutanoate
  2. BExcess in dry ether, followed by aqueous work-up, gives butane-1,3-diol
  3. C in ethanol at 0 gives butane-1,3-diol
  4. D, hot in ethylene glycol leaves the ester group unchanged

Answer: A, B

reduces only the ketone, giving the hydroxy ester. reduces both ketone and ester to alcohols, giving butane-1,3-diol (ethanol is also released). Hot hydrolyses the ester, so the last statement is wrong.
Practice Aldehydes, Ketones and Carboxylic Acids More on Oxidation and reduction of carbonyls (Clemmensen, Wolff-Kishner, Tollens, Fehling)

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