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COMEDK202510 May 2025Evening ShiftChemistryAldehydes and KetonesActual

An organic compound "A" reacts with Zn / Hg / Conc. HCl to form p-Xylene. It reduces Tollen's reagent and on oxidation with KMnO ₄ / H ⁺ it yields 1, 4-benzenedicarboxylic acid. Identify compound A .

Options

  1. Am- Cresol.
  2. B4-Methylacetophenone.
  3. Cp-methylbenzaldehyde.
  4. Dp- Cresol.

Correct answer

C. p-methylbenzaldehyde.

Step-by-step solution

The compound A reacts with Zn/Hg/Conc. HCl (Clemmensen reduction) to form p-Xylene. This indicates that the carbonyl group of an aldehyde or ketone is reduced to a methylene group. The structure of p-Xylene is 1,4 -dimethylbenzene. The compound A reduces Tollen's reagent, which is a characteristic test for aldehydes. Therefore, A must be an aldehyde. Oxidation of A with KMnO ₄/ H ⁺ yields 1,4 -benzenedicarboxylic acid (terephthalic acid). This confirms that A has two substituents at the para positions, one of which

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