Question:

Compound \(P\) gives a red-orange precipitate with 2,4-DNP reagent and does not reduce Fehling's reagent. On drastic oxidation with chromic acid, \(P\) gives an aromatic product \(Q\) which produces effervescence on treating with aqueous \(\ce{NaHCO3}\). Compounds \(P\) and \(Q\), respectively, are:

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2,4-DNP confirms carbonyl group, Fehling negative suggests ketone, and \(\ce{NaHCO3}\) effervescence confirms carboxylic acid.
Updated On: May 3, 2026
  • Acetophenone and benzoic acid
  • Acetophenone and phenylacetic acid
  • Benzaldehyde and benzoic acid
  • Phenol and benzoic acid
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The Correct Option is A

Solution and Explanation


Step 1: Interpret 2,4-DNP test.

2,4-DNP reagent gives red-orange precipitate with compounds having carbonyl group. Carbonyl compounds include: \[ \text{aldehydes and ketones}. \] So compound \(P\) must contain: \[ >C=O \]

Step 2: Interpret Fehling's test.

Fehling's reagent is reduced by aliphatic aldehydes. The question says \(P\) does not reduce Fehling's reagent. So \(P\) is not an aliphatic aldehyde. It is most likely a ketone.

Step 3: Identify \(P\).

Among aromatic carbonyl compounds, acetophenone is: \[ \ce{C6H5COCH3} \] It is an aromatic ketone. It gives 2,4-DNP test but does not reduce Fehling's reagent. So: \[ P=\text{Acetophenone}. \]

Step 4: Oxidation of acetophenone.

On strong oxidation, side chain of alkyl benzene or aryl ketone is converted into: \[ \ce{-COOH} \] Thus, acetophenone gives: \[ \ce{C6H5COOH} \] This is benzoic acid.

Step 5: Sodium bicarbonate test.

Carboxylic acids react with sodium bicarbonate to produce carbon dioxide gas. \[ \ce{RCOOH + NaHCO3 -> RCOONa + CO2 + H2O} \] Effervescence confirms carboxylic acid. Therefore: \[ Q=\text{Benzoic acid}. \] Hence: \[ P=\text{Acetophenone},\quad Q=\text{Benzoic acid}. \]
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