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Practical Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q4
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Practical Organic Chemistry question

2019 · 8 Apr · Shift 1 · Q4

JEE MainChemistryPractical Organic ChemistryMCQ+4 / −1
An organic compound 'X' showing the following solubility profile is : JEE Main 2019 (Online) 8th April Morning Slot Chemistry - Practical Organic Chemistry Question 79 English
  1. A
    o-Toluidine
  2. B
    Benzamide
  3. C
    Oleic acid
  4. D
    m-Cresol
View written solutionFree

Correct answer: D

  1. In practical organic analysis, solubility behavior is used to identify the functional group.

  2. The usual diagnostic pattern for the given options is:

    • Carboxylic acids dissolve in NaHCO3\mathrm{NaHCO_3}NaHCO3​ as well as NaOH\mathrm{NaOH}NaOH.
    • Phenols dissolve in NaOH\mathrm{NaOH}NaOH but not in NaHCO3\mathrm{NaHCO_3}NaHCO3​.
    • Amines dissolve in dilute HCl\mathrm{HCl}HCl.
    • Amides are generally neutral and do not show such acidic/basic solubility.
  3. Now check each option:

    A: ooo-Toluidine

    • It is an amine.
    • It should dissolve in dilute HCl\mathrm{HCl}HCl due to salt formation.
    • So this does not match a phenolic solubility profile.

    B: Benzamide

    • It is an amide.
    • It is neutral and does not characteristically dissolve in NaOH\mathrm{NaOH}NaOH like a phenol.
    • So this is not the correct match.

    C: Oleic acid

    • It is a carboxylic acid.
    • It should dissolve in NaHCO3\mathrm{NaHCO_3}NaHCO3​ and NaOH\mathrm{NaOH}NaOH.
    • Hence it would not fit a profile of dissolving only in strong base.

    D: mmm-Cresol

    • It is a phenol.
    • Phenols dissolve in NaOH\mathrm{NaOH}NaOH but not in NaHCO3\mathrm{NaHCO_3}NaHCO3​.
    • This matches the characteristic practical organic solubility profile.
  4. Therefore, compound XXX is mmm-Cresol.

Option D: m-Cresol\boxed{\text{Option D: } m\text{-Cresol}}Option D: m-Cresol​

  1. Comparison with stored correct answer:
    • Stored correct answer: D
    • Derived answer: D
    • They match.
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