One or more options correct
Which of the following statement(s) about aromatic compounds is/are correct?
- A. Anisole, heated with excess concentrated HI, gives iodobenzene and methanol.
- B. Direct nitration of aniline with a mixture gives p-nitroaniline as the exclusive product.
- C. Phenol, on heating with chloroform and aqueous NaOH followed by acidification, gives salicylaldehyde as the major product.
- D. Toluene, treated with in the presence of sunlight, gives a mixture of o- and p-chlorotoluene.
Show answer and solution
Answer: C
Option C is correct: in the Reimer-Tiemann reaction the phenoxide attacks dichlorocarbene, mainly at the ortho position, and hydrolysis gives o-hydroxybenzaldehyde. Option A is wrong because the aryl C-O bond does not break; the protonated ether is attacked by iodide at the methyl group (SN2), so phenol and methyl iodide form, and excess HI cannot convert phenol into iodobenzene. Option B is wrong because in the strongly acidic nitrating mixture aniline is protonated to the anilinium ion, a meta director, so a large fraction of m-nitroaniline (plus oxidation products) forms. Option D is wrong because sunlight promotes a free-radical substitution on the side chain, giving benzyl chloride, whereas ring chlorination needs a Lewis acid. Only C is correct.
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