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DPP 33

The document outlines various methods for the reduction of nitrobenzene, including alkaline, acidic, and neutral medium reductions, as well as catalytic and metallic hydride reductions. It highlights specific reducing agents and conditions for each method, such as Zn/NaOH and H2/Pd. Additionally, it discusses the selective reduction of dinitrobenzene using mild reducing agents to target one nitro group without affecting others.

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59 views2 pages

DPP 33

The document outlines various methods for the reduction of nitrobenzene, including alkaline, acidic, and neutral medium reductions, as well as catalytic and metallic hydride reductions. It highlights specific reducing agents and conditions for each method, such as Zn/NaOH and H2/Pd. Additionally, it discusses the selective reduction of dinitrobenzene using mild reducing agents to target one nitro group without affecting others.

Uploaded by

anushah1.gupta
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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DPP # 33

Reduction of Nitrobenzene

ALKALINE MEDIUM REDUCTION


O
N=N N=N NH–NH
(Azoxybenzene) (Azobenzene) (Hydrazobenzene)
or Glucose / NaOH

Zn/NaOH, CH3OH

Zn/NaOH, CH3OH
Na3AsO3/NaOH

–4H2O

–4H2O
–3H2O

10[H]
6[H]

8[H]
ELECTROLYTIC REDUCTION

ACIDIC MEDIUM REDUCTION


NH2
Weakly
acidic medium

NH2 NHOH NO2 NH2


Strongly
Rearrangement acidic medium Sn/Conc. HCl
Fe/Conc. HCl
(N-phenyl (Aniline)
OH
Zn/aq. NH4Cl

(p-aminophenol) hydroxyl amine)

Alkaline
H 2N NH2 medium

(Benzidine) NHOH

(N-phenyl
hydroxyl amine)

NEUTRAL MEDIUM REDUCTION

1
Catalytic Reduction:
NO2 NH2
H2/Pd, EtOH

(Aniline)
Metallic Hydride:
NO2
LiAlH4 Ph–N=N–Ph
(Azobenzene)

Selective Reduction of Dinitrobenzene


When more than one nitro groups are attached to aromatic nucleus, then selective reduction of
one of the –NO2 group can be achieved without affecting another nitro group by using very mile
reducing agents like ammonium sulphide (NH4)2S / sodium polysulphide Na2Sx / NH3-H2S
NO2 NO2

+ 3 (NH4)2S  + 6NH3 + 2H2O + 3S


NO2 NO2

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