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Example · Example 3

Q.Nitrobenzene is reduced with Zn\text{Zn} dust and aqueous NH4Cl\text{NH}_4\text{Cl} (a neutral, mild reducing medium). Identify the product formed and explain why this reagent combination stops the reduction at an intermediate stage rather than going all the way to aniline.

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✓ Free question

Zn\text{Zn} dust in neutral aqueous NH4Cl\text{NH}_4\text{Cl} is a deliberately mild reducing medium: it supplies enough reducing power to take nitrobenzene through the nitroso stage to the hydroxylamine, C6H5NHOH\text{C}_6\text{H}_5\text{NHOH}, but the near-neutral pH is not strong enough to complete the final two-electron step through to the fully reduced amine. This makes Zn/NH4Cl\text{Zn}/\text{NH}_4\text{Cl} the reagent of choice specifically when the partially-reduced hydroxylamine is the target, rather than aniline.

✓Final answer

Phenylhydroxylamine, C6H5NHOH\text{C}_6\text{H}_5\text{NHOH}.

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