NEET 2026 Chemistry Question 86 Solution
Question
Consider the following reaction, and choose the correct option. Toluene → i. CrO₂Cl₂, CS₂ ii. H₃O⁺ → P
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Consider the following reaction, and choose the correct option. Toluene → i. CrO₂Cl₂, CS₂ ii. H₃O⁺ → P
Toluene + Chromyl Chloride (CrO₂Cl₂) = Étard Reaction producing BENZALDEHYDE (P)!
Chromyl chloride (CrO₂Cl₂) in a non-polar solvent like CS₂ oxidizes the methyl group of toluene into a brown chromium complex [C₆H₅CH(OCrOHCl₂)₂]. Hydrolysis of this intermediate yields benzaldehyde.
Rosenmund reduction involves catalytic hydrogenation of an acyl chloride (benzoyl chloride) over palladium catalyst supported on barium sulfate (Pd/BaSO₄), partially poisoned with sulfur or quinoline to prevent over-reduction to an alcohol.
1. Statement (1): Benzaldehyde is an aldehyde, not a carboxylic acid; it does NOT release CO₂ gas with NaHCO₃ (no brisk effervescence). 2. Statement (2): Benzene + CH₃COCl/AlCl₃ is Friedel-Crafts acylation, producing Acetophenone (PhCOCH₃), not benzaldehyde. 3. Statement (3): Bromine water gives white precipitates with phenol (2,4,6-tribromophenol) or aniline, not benzaldehyde.
Diagnose every choice: Know exactly why the right option works and why distractors fail.
Incorrect. Benzaldehyde is not acidic enough to decompose bicarbonate to CO₂.
Incorrect. Friedel-Crafts acylation of benzene with acetyl chloride yields acetophenone, not benzaldehyde.
Incorrect. White precipitate with bromine water is a test for phenol or aniline, not benzaldehyde.
Exact match: Rosenmund reduction of benzoyl chloride over Pd/BaSO₄ gives benzaldehyde (Compound P).
Vigorous oxidizers like alkaline KMnO₄ oxidize toluene to benzoic acid. But CrO₂Cl₂ (Étard reaction) is specifically designed to STOP at the aldehyde stage (Benzaldehyde)!
"Toluene + CrO₂Cl₂ yields benzaldehyde; Benzoyl chloride + H₂/Pd-BaSO₄ also yields benzaldehyde."
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