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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1233

The keto nitrile shown is treated with an excess of lithium aluminium hydride in dry ether, followed by aqueous work-up. Which structure is the product?

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

Answer: A

4-Oxopentanenitrile has a ketone and a nitrile. Lithium aluminium hydride reduces the ketone to a secondary alcohol and the nitrile to a primary amine (CH2NH2), giving 5-aminopentan-2-ol. Sodium borohydride would reduce only the ketone, and the keto amine would retain a carbonyl.
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