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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro230

The lactone shown is treated with various hydride reagents followed by aqueous work-up. Select ALL correct statements.

  1. AExcess gives a diol with the two hydroxyl groups on carbons 1 and 4 of a five-carbon chain.
  2. B (1 equivalent, ) can stop at the lactol (cyclic hemiacetal) stage.
  3. C in methanol at room temperature reduces the lactone rapidly to the diol.
  4. DThe diol obtained with contains one stereocentre.

Answer: A, B, D

The compound is gamma-valerolactone. Excess opens the ring and reduces the acyl carbon to , giving pentane-1,4-diol (true), which has one stereocentre at C4 (true). With one equivalent of DIBAL-H at the reduction stops at the lactol (true). does not reduce simple lactones/esters at room temperature, so statement 3 is false.
Practice Reduction, Oxidation and Hydrolysis in Organic Chemistry More on Hydride reductions of drawn compounds (LiAlH4 / NaBH4 / DIBAL-H)

More questions on Hydride reductions of drawn compounds (LiAlH4 / NaBH4 / DIBAL-H)