JEE Advanced · 2017 · 21 May 2017 · Paper 2 · Compounds Containing Nitrogen

The major product of the following reaction is

(see structure)

(A)(see structure)
(B)(see structure)
(C)(see structure)
✓ Correct
(D)(see structure)

Answer: (C)

Solution

The reaction involves an intramolecular cyclization of a diazonium compound. The diazonium group attacks the adjacent aromatic ring in an electrophilic aromatic substitution, forming a fused ring system. The hydroxyl group directs the cyclization to the ortho position, resulting in the formation of a naphthol derivative with the azo linkage incorporated into the ring system. The product is a hydroxylated benzocinnoline structure.

JEE Advanced · 2017 · 21 May 2017 · Paper 2 · Single correct option

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