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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3si217

Toluene is treated with in and then hydrolysed with water to give X. Which of the following statements about X are correct?

  1. AX gives a silver mirror with Tollens reagent.
  2. BX gives a red precipitate with Fehling solution.
  3. CX gives a yellow to orange precipitate with 2,4-DNP.
  4. DX undergoes the Cannizzaro reaction with concentrated NaOH.

Answer: A, C, D

Etard's reaction converts toluene to benzaldehyde (X). Benzaldehyde reduces Tollens reagent and forms a 2,4-dinitrophenylhydrazone. It has no alpha hydrogen and gives the Cannizzaro reaction. Aromatic aldehydes do not reduce Fehling solution, so (B) is wrong.
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