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Distinction between pairs of compounds ...

Distinction between pairs of compounds
Aniline and Nitrobenzene

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Aniline being a primary aromatic amine gives carbylamine test as well as azo dye test. However those tests are not given by nitrobenzene. On the other hand, nitrobenzene gives Barker-Mulliken.s test which is not given by aniline.
Barker-Mulliken.s test. Nitrobenzene on reduction with Zn and `NH_(4)Cl` solution (neutral medium) gives N-phenylhydroxylamine which reduces Tollens. reagent to give silver mirror.
`C_(6)H_(5)NO_(2)+4Hoverset(Zn//NH_(4)Cl)rarrunderset("N-Phenylhydroxylamine")(C_(6)H_(5)NHOH+H_(2)O)`
`C_(6)H_(5)NHOH+2[Ag(NH_(3))_(2)]OH`
`rarrunderset("Nitroosobenzene")(C_(6)H_(5)-N)=O+underset("Silver mirror")(Ag)+4NH_(3)+2H_(2)O`
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