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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro232

The compound shown is treated with excess in ether, followed by aqueous work-up. Hydride attacks the less hindered carbon of the three-membered ring. Which structure is the final organic product?

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

Answer: C

The compound is methyl 2-(oxiran-2-yl)acetate. The ester is reduced to (methanol is lost). Hydride opens the epoxide at the terminal (SN2 at the less hindered carbon), turning it into a methyl group and leaving the secondary alcohol on the other carbon. The product is butane-1,3-diol. Attack at the more substituted carbon would give butane-1,4-diol.
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More questions on Hydride reductions of drawn compounds (LiAlH4 / NaBH4 / DIBAL-H)