JEE Main 2022 · 29 July · morning · Single correct · +4 / −1

A compound 'X' is acidic and it is soluble in NaOH solution, but insoluble in NaHCO₃ solution. Compound 'X' also gives violet colour with neutral FeCl₃ solution. The compound 'X' is :

  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (b)

Solution

Chemistry ma’am · 4 steps

Three clues, one answer: NaOH yes, NaHCO3 no, violet with FeCl3 means an OH sitting right on a benzene ring.

  1. Read the options. (a) is cyclohexanol, (b) is phenol, (c) is benzyl alcohol, C₆H₅CH₂OH, and (d) is cyclohexylmethanol. All four have an -OH group, but only in (b) is it bonded directly to the ring carbon of a benzene ring.
  2. Acid strength test. NaOH dissolves any acid stronger than water, but NaHCO₃ dissolves only acids stronger than carbonic acid, such as carboxylic acids. So 'X' is a weak acid: stronger than water, weaker than H₂CO₃.
    CompoundSoluble in NaOHSoluble in NaHCO₃Violet with neutral FeCl₃
    (a) cyclohexanolnonono
    (b) phenolyesnoyes
    (c) benzyl alcoholnonono
    (d) cyclohexylmethanolnonono
  3. Why phenol. In phenol the negative charge of the phenoxide ion spreads into the ring by resonance, so phenol (pKₐ ≈ 10) is acidic enough to react with NaOH but not with NaHCO₃. The -OH on the aromatic ring also forms a violet complex with Fe³⁺.
  4. So. Every clue fits only phenol, so 'X' is option (b).

The idea to keep. Soluble in NaOH but not in NaHCO3 means a phenol, not a carboxylic acid. A violet colour with neutral FeCl3 confirms an OH bonded directly to an aromatic ring.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 40 times in JEE Main since 2020. This question is from 2022.