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NEST2026ChemistryHydrocarbons

1,2-dimethylbenzene on treatment with chromic oxide in acetic anhydride at 273 - 283 K followed by hydrolysis produces P. P on heating with concentrated NaOH followed by hydrolysis provides Q. The functional groups present in the product Q are:

Options

  1. AOne carboxylic acid and one alcohol
  2. BTwo carboxylic acids
  3. CTwo aldehydes
  4. DOne aldehyde and one carboxylic acid

Correct answer

A. One carboxylic acid and one alcohol

Step-by-step solution

1,2-dimethylbenzene reacts with CrO₃ in acetic anhydride at 273 - 283 K to form a gem-diacetate intermediate at both methyl groups. Hydrolysis of this intermediate yields benzene-1,2-dicarbaldehyde (P). Benzene-1,2-dicarbaldehyde lacks -hydrogens. On heating with concentrated NaOH, it undergoes an intramolecular Cannizzaro reaction. One aldehyde group is oxidized to a sodium carboxylate group ( -COO⁻Na⁺ ), and the other is reduced to a primary alcohol group ( -CH₂OH ). Subsequent acidification yields 2-(hydroxymeth

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