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Question 44 of 69

Q.When nitromethane is reduced with Zn/NH4ClZn/NH_4Cl, we get :

(a) CH3NH2CH_3NH_2
(b) C2H5NH2C_2H_5NH_2
(c) CH3NHOHCH_3NHOH
(d) C2H5COOHC_2H_5COOH
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2017MCQ· 1mImportance★★★★★
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Nitromethane with Zn/NH4_4Cl (neutral reducing conditions) is only partially reduced, stopping at N-methylhydroxylamine.

Complete reduction of a nitro compound (e.g. with Sn/HCl or Fe/HCl or H2_2/Ni) gives the primary amine, but Zn dust with NH4_4Cl solution is a classical mild, neutral-medium reducing system that arrests the reduction sequence R−NO2→R−NO→R−NHOH→R−NH2R-NO_2 \rightarrow R-NO \rightarrow R-NHOH \rightarrow R-NH_2 at the intermediate N-substituted hydroxylamine stage. So CH3NO2CH_3NO_2 gives CH3NHOHCH_3NHOH (N-methylhydroxylamine), not the amine. Options (a) and (b …

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