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Chemistry · Ch 9 — Amines

Reduction of Nitro Compounds

9.4.1

Reduction of Nitro Compounds

Reduction of Nitro Compounds

The most direct route to a primary amine is to start from the corresponding nitro compound and simply reduce the −NO2-\text{NO}_2 group down to −NH2-\text{NH}_2. This works for both aromatic nitro compounds (nitrobenzene and its derivatives) and aliphatic nitroalkanes — the reduction chemistry is the same in either case.

Two practical ways of carrying out this reduction are used.

Catalytic hydrogenation

Hydrogen gas is passed over the nitro compound in the presence of a finely divided hydrogenation catalyst — nickel, palladium, or platinum:

Catalytic hydrogenation of nitrobenzene: hydrogen gas over a palladium catalyst in ethanol reduces the ring's nitro group to an amino group, giving aniline.
Catalytic hydrogenation of nitrobenzene: hydrogen gas over a palladium catalyst in ethanol reduces the ring's nitro group to an amino group, giving aniline.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (NO2, NH2) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so what …

Reduction with metal and acid

Alternatively, the nitro compound is reduced with a metal in acidic medium — tin with hydrochloric acid, or iron with hydrochloric acid:

Reduction of nitrobenzene with metal and acid: tin with hydrochloric acid, or iron with hydrochloric acid, converts the nitro group to an amino group, giving aniline.
Reduction of nitrobenzene with metal and acid: tin with hydrochloric acid, or iron with hydrochloric acid, converts the nitro group to an amino group, giving aniline.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (NO2, NH2) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so what …

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