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Practical Organic Chemistry question

2011 · Shift 0 · Q15
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Practical Organic Chemistry question

2011 · Shift 0 · Q15

JEE MainChemistryPractical Organic ChemistryMCQ+4 / −1
Which of the following reagents may be used to distinguish between phenol and benzoic acid ?
  1. A
    Tollen’s reagent
  2. B
    Molisch reagent
  3. C
    Neutral FeCl3FeCl_3FeCl3​
  4. D
    Aqueous NaOH
View written solutionFree

Correct answer: C

  1. Identify the functional groups

    • Phenol: aromatic compound containing the group −OH-OH−OH directly attached to benzene.
    • Benzoic acid: aromatic carboxylic acid containing the group −COOH-COOH−COOH.
  2. Check each reagent

    A. Tollen’s reagent

    • Tollen’s reagent is used mainly to detect aldehydes.
    • Neither phenol nor benzoic acid gives the characteristic silver mirror test.
    • Hence, it cannot distinguish between them.

    B. Molisch reagent

    • Molisch reagent is used to test for carbohydrates.
    • Neither phenol nor benzoic acid is a carbohydrate.
    • Hence, it cannot distinguish between them.

    C. Neutral FeCl3FeCl_3FeCl3​

    • Phenols give a colored complex (violet/purple/blue/green depending on structure) with neutral ferric chloride.
    • Benzoic acid does not give this characteristic phenol test.
    • Therefore, neutral FeCl3FeCl_3FeCl3​ can distinguish between phenol and benzoic acid.

    D. Aqueous NaOHNaOHNaOH

    • Phenol reacts with NaOHNaOHNaOH to form sodium phenoxide: C6H5OH+NaOH→C6H5ONa+H2OC_6H_5OH + NaOH \rightarrow C_6H_5ONa + H_2OC6​H5​OH+NaOH→C6​H5​ONa+H2​O
    • Benzoic acid also reacts with NaOHNaOHNaOH to form sodium benzoate: C6H5COOH+NaOH→C6H5COONa+H2OC_6H_5COOH + NaOH \rightarrow C_6H_5COONa + H_2OC6​H5​COOH+NaOH→C6​H5​COONa+H2​O
    • Since both dissolve/react with aqueous NaOHNaOHNaOH, it does not distinguish between them.
  3. Conclusion The reagent that distinguishes phenol from benzoic acid is: C. Neutral FeCl3\boxed{\text{C. Neutral } FeCl_3}C. Neutral FeCl3​​

  4. Comparison with stored correct answer

    • Derived answer: CCC
    • Stored correct answer: CCC
    • They match.
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