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 :
- (a)
- (b)
- (c)
- (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.
- 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.
- 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.
Compound Soluble in NaOH Soluble in NaHCO₃ Violet with neutral FeCl₃ (a) cyclohexanol no no no (b) phenol yes no yes (c) benzyl alcohol no no no (d) cyclohexylmethanol no no no - 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⁺.
- 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.