Question:

An organic compound A (\(\mathrm{C_6H_6O}\)) gives dark green colouration with ferric chloride. On treatment with \(\mathrm{CHCl_3}\) and KOH, followed by acidification gives compound B. Compound B can also be obtained from compound C on reaction with pyridinium chlorochromate (PCC). Identify A, B and C.

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Ferric chloride colour test and C6H6O indicate phenol; Reimer-Tiemann gives salicylaldehyde, which can come from salicyl alcohol by PCC oxidation.
Updated On: Nov 4, 2026
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The Correct Option is A

Solution and Explanation

A: \(\mathrm{C_6H_6O}\) giving a dark green/violet colour with \(\mathrm{FeCl_3}\) is phenol.
B: phenol + \(\mathrm{CHCl_3}\)/KOH (Reimer-Tiemann), then acidification, gives salicylaldehyde (2-hydroxybenzaldehyde).
C: salicylaldehyde is obtained from 2-hydroxybenzyl alcohol (salicyl alcohol) by mild oxidation with PCC, which stops at the aldehyde stage.
So A = phenol, B = salicylaldehyde, C = salicyl alcohol, which is the set drawn in option (1).
Answer: (1) A = phenol, B = salicylaldehyde, C = 2-hydroxybenzyl alcohol
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