Question:

Coupling of benzene diazonium chloride with 1 - naphthol in alkaline medium will give :

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Azo coupling is an electrophilic substitution on the activated naphthoxide ion; the electrophile enters para (position 4) to the O- group.
Updated On: Nov 5, 2026
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The Correct Option is C

Solution and Explanation

In alkaline medium 1-naphthol exists as the 1-naphthoxide ion, a strongly activated ring (the \(\mathrm{O^-}\) group is a powerful +M group).
The benzene diazonium cation \(\mathrm{C_6H_5N_2^+}\) is a weak electrophile and attacks the position of highest electron density: the ortho (C-2) or para (C-4) position relative to \(\mathrm{O^-}\). Attack at C-4 (para) is preferred over C-2 because it avoids steric hindrance with the \(\mathrm{O^-}\) group.
Product: 4-(phenylazo)-1-naphthol (an orange-red azo dye), with \(\mathrm{Ph-N=N}\) at C-4 and \(\mathrm{OH}\) at C-1 of the same ring.
From the images: option (1) has the azo group on the other ring (C-5), option (2) at C-2 (ortho), option (3) at C-4 (para), option (4) at C-3 (meta). The para product is option (3).
Answer: (3) 4-(phenylazo)-1-naphthol (azo group para to OH)
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