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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Mark the reaction among the following that does not give benzoic acid as the major product:

A

C6H5COCH3(i) NaOBr (ii) H+C_6H_5COCH_3 \xrightarrow{\text{(i) } NaOBr \text{ (ii) } H^+}

B

C6H5CH3KMnO4/KOH,ΔC_6H_5CH_3 \xrightarrow{KMnO_4/KOH, \Delta}

C

C6H5CNH3O+C_6H_5CN \xrightarrow{H_3O^+}

D

C6H5CH2OHPCCC_6H_5CH_2OH \xrightarrow{\text{PCC}}

Step-by-Step Solution

The question tests the knowledge of oxidation reactions yielding carboxylic acids versus aldehydes.

  1. Haloform Reaction: Acetophenone (C6H5COCH3C_6H_5COCH_3) contains a methyl ketone group. Treatment with NaOBrNaOBr (sodium hypobromite) followed by acidification oxidises it to Benzoic acid (C6H5COOHC_6H_5COOH).
  2. Side-Chain Oxidation: Alkylbenzenes like Toluene (C6H5CH3C_6H_5CH_3) having at least one benzylic hydrogen are oxidised by strong oxidising agents like alkaline KMnO4KMnO_4 to Benzoic acid.
  3. Hydrolysis of Nitriles: Benzonitrile (C6H5CNC_6H_5CN) upon complete acid hydrolysis (H3O+H_3O^+) yields Benzoic acid.
  4. Mild Oxidation: PCC (Pyridinium Chlorochromate) is a mild oxidising agent used to convert primary alcohols to aldehydes. It prevents further oxidation to carboxylic acids. Therefore, the reaction of Benzyl alcohol (C6H5CH2OHC_6H_5CH_2OH) with PCC yields Benzaldehyde (C6H5CHOC_6H_5CHO), not benzoic acid.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersreactionfollowingbenzoicproduct

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