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JEE Main levelSingle correct optionDifficulty 2 of 3o1081

5-Hydroxypentanal in solution exists largely as

  1. Aa cyclic acetal with two ring oxygens
  2. Ba six-membered cyclic hemiacetal (oxan-2-ol)
  3. Ca five-membered cyclic ketal
  4. Dits open-chain gem-diol

Answer: B

The hydroxyl at C-5 adds intramolecularly to the aldehyde carbon, closing a six-membered ring containing one oxygen: tetrahydropyran-2-ol. Cyclic hemiacetals of this size are favoured over the open-chain form, and no second alcohol is available to give a full acetal.
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