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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1245

The hydroxy aldehyde shown is dissolved in an excess of methanol containing a catalytic amount of dry HCl. Which structure is the major product?

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

Answer: C

5-Hydroxypentanal cyclises spontaneously, the OH adding to the aldehyde to form the six-membered cyclic hemiacetal tetrahydropyran-2-ol. In dry acid and excess methanol the hemiacetal OH is replaced through an oxocarbenium ion by OMe, giving the cyclic mixed acetal 2-methoxytetrahydropyran. The hemiacetal alone is only the intermediate.
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