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
- AOne carboxylic acid and one alcohol
- BTwo carboxylic acids
- CTwo aldehydes
- 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