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Question 39

The correct stability order of the following diazonium salts is

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To determine the decreasing order of stability for the given benzenediazonium salts, we must evaluate the electronic effects of the substituents on the benzene ring. The stability of a diazonium ion depends heavily on how well the positive charge on the nitrogen atoms can be dispersed.

Electron-donating groups (+R effect) push electron density into the ring, which helps neutralize and delocalize the positive charge on the diazonium group, thereby increasing stability. Conversely, electron-withdrawing groups (-R effect) pull electron density away from the ring, which intensifies the positive charge and decreases stability.

In compound (A), the methoxy group (-OCH₃) exhibits a strong electron-donating +R effect, making the diazonium ion the most stable. Compound (C) has no substituent and serves as the neutral baseline. In compounds (D) and (B), the cyano (-CN) and nitro (-NO₂) groups act as powerful electron-withdrawing groups via the -R effect, highly destabilizing the ion. Because the nitro group exerts a stronger electron-withdrawing effect than the cyano group, compound (B) is the least stable of all.

Therefore, the decreasing order of stability is: (A) > (C) > (D) > (B).

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