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JEE Advanced levelSingle correct optionDifficulty 3 of 3co092

Ethanal is heated with excess methanal and . Three successive crossed aldol additions occur at the alpha carbon, and the resulting trihydroxy aldehyde is then reduced by a crossed Cannizzaro reaction with methanal. The final organic product is

  1. A3-hydroxy-2,2-bis(hydroxymethyl)propanal
  2. Bpropane-1,2,3-triol
  3. C2,2-bis(hydroxymethyl)propane-1,3-diol
  4. D2-(hydroxymethyl)propane-1,3-diol

Answer: C

Ethanal has three alpha-hydrogens and each adds to a methanal, giving . This aldehyde has no alpha-hydrogen, so with methanal it undergoes crossed Cannizzaro reaction; methanal is oxidised and the aldehyde is reduced. The product is , pentaerythritol.
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