JEE Main Chemistry question

Nitrosobenzene (C₆H₅–N=O) is best obtained by oxidation of *N*-phenylhydroxylamine, and is **not** cleanly isolated directly from nitrobenzene under any of the following reduction conditions:

(A)Metal and acid (e.g. Sn/HCl — reduces all the way to aniline)
(B)Zn dust and aqueous NH₄Cl (halts reduction at *N*-phenylhydroxylamine, one stage short of nitrosobenzene)
(C)Alkaline sodium arsenite (drives reduction further, toward azoxy-/azo-/hydrazo-benzene)
(D)None of the aboveCorrect

Answer: (D)

Solution

Each listed reagent either over-reduces nitrobenzene past the nitroso stage (metal/acid to aniline; alkaline arsenite toward azoxy- and azo-compounds) or stops one step short of it (Zn/NH₄Cl, which

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Question ID VK-140279