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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1158

2,2-Dimethoxypropane is hydrolysed in aqueous acid made with (water enriched in oxygen-18). Where does the end up?

  1. Ain methanol only
  2. Bin acetone only
  3. Cin both acetone and methanol
  4. Din neither product

Answer: B

Hydrolysis proceeds by protonation of an OCH3 group and loss of (C-O cleavage at the acetal carbon, with the original oxygen leaving as methanol). The oxocarbenium ion is attacked by , and after loss of the second methanol the carbonyl oxygen comes from water. So the label is in acetone and not in methanol.
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