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Organic Compounds Having Nitro (NO) Group As Functional Group Nitroalkanes Are Isomeric With Alkyl Nitrites R - N - O R - O - N O

The document discusses nitro compounds, which contain the nitro (NO2) functional group. It describes the classification, nomenclature, preparation, properties, and reactions of aliphatic nitro compounds and aromatic nitro compounds like nitrobenzene. Nitro compounds can be prepared by reacting haloalkanes, alkanes, or benzene with nitric acid. They undergo reduction, hydrolysis, electrophilic substitution, and other reactions.

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167 views14 pages

Organic Compounds Having Nitro (NO) Group As Functional Group Nitroalkanes Are Isomeric With Alkyl Nitrites R - N - O R - O - N O

The document discusses nitro compounds, which contain the nitro (NO2) functional group. It describes the classification, nomenclature, preparation, properties, and reactions of aliphatic nitro compounds and aromatic nitro compounds like nitrobenzene. Nitro compounds can be prepared by reacting haloalkanes, alkanes, or benzene with nitric acid. They undergo reduction, hydrolysis, electrophilic substitution, and other reactions.

Uploaded by

Paras gurung
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Nitro compounds

Organic compounds having nitro (NO2) group as functional group


Nitroalkanes are isomeric with alkyl nitrites
R – N –> O R–O–N=O
||
O
Classification

1) Aliphatic nitro compounds 1) Primary nitro compounds


2) Aromatic nitro compounds 2) Secondary nitro compounds
3) Tertiary nitro compounds
Nomenclature:
NO2 NO2 NO2
CH3 – NO2
| NO2
nitromethane C H3C CH3
|
C2H5– NO2 NO2
2,2-dinitro propane NO2 NO2
nitroethane 1,3-dinitrobenzene 1,2,3-trinitrobenzene
NO2
C H3CH CH3
|
NO2

2-nitropropane
nitrobenzene
C H3C(CH3)2 – NO2
2-methyl-2-nitro propane
Preparation of nitro compounds
1) From haloalkane : (can’t be used to prepare aromatic)
R-X + AgNO2 alcohol R-NO2 + AgI
1° ∆
(especially bromides & iodides)

Use of AgNO2 Use of NaNO2 / KNO2


Nitroalkane is formed Alkylnitrite is formed
Reason Reason
AgNO2 is covalent compound NaNO2 / KNO2 are ionic compounds
Lone pair of electron present on N Lone pair of electron present on O
atom acts as attacking site atom acts as attacking site
2) From alkane : (can be used to prepare both aliphatic & aromatic)
400 °C
CH4 + HNO3 CH3NO2 + H2 O
Fumming
400 °C
CH3CH3 + HNO3 CH 3CH2NO2 + CH3NO2 + H2O
Fumming
400 °C
CH3CH2CH3 + HNO3 CH3CH2CH2NO2 + CH3CH2NO2
Fumming + CH3NO2 + H2O
Mixture of different nitroalkanes are formed

Alkanes are inert to nitration so vapour phase nitration is done

Ease of abstraction of hydrogen is 3° > 2° >1 °


Conc. H2SO4

NO2
+ conc. HNO3 + H 2O
50-60 °C

Laboratory preparation of nitrobenzene NO2


Principle
Conc. H2SO4
+ conc. HNO3 60 °C + H 2O
nitrobenzene (oil of mirbane)
Benzene
NO2

+ conc. HNO3 Conc. H2SO4 + H 2O


above 60 °C
NO2
Procedure
nitrating mixture
(150ml) added little
by little, shaking &
cooling after each
addition

Benzene (25 ml)

Reflux for 1.5 hours


at 60 °C

Yellow oily liquid nitrobenzene


Purification:

• First washed with dil. Na2CO3 solution to remove acidic impurities


then with water for several times
• Then it is dried over anhydrous CaCl2
• At last it is redistilled at the temperature range 211 °C (b.pt. 210 °C)
to get pure and dry nitrobenzene
Physical properties
Nitro compounds Nitrobenzene

Colorless, pleasant smelling liquid Pale yellow, bitter almond smelling oily liquid
Sparingly soluble in H2O Insoluble in H2O
Highly soluble in organic solvents Highly soluble in organic solvents

more polar than hydrocarbon Highly toxic because vapours readily


absorbed through skin
Chemical properties
1) Reduction in acidic medium (Zn,Sn,Fe etc with conc. HCl)
Nitroalkanes are reduced to primary amines
Sn / HCl CH3 – NH2 + 2 H2O
CH3 – NO2 + 6 H
Sn / HCl CH3CH2 – NH2 + 2 H2O
CH3 CH2 – NO2 + 6 H

Nitrobenzene is reduced to aniline

NO2 NH2

+ 6H Zn / HCl + H 2O
2) Reduction in neutral medium (Zn dust and NH4Cl solution)
Nitroalkanes are reduced to hydroxyl amines

CH3 – NO2 + 4 H Zn / NH4Cl CH3 – NH + 2 H2O


|
OH
N- methyl hydroxylamine

Nitrobenzene is reduced to N-phenyl hydroxylamine


NO2 NH – OH

+ 4H Zn / NH4Cl
+ H 2O
3) Catalytic reduction ( hydrogen with Ni / Pt / Pd)
Nitroalkanes are reduced to primary amines

CH3 – NO2 + H2 Ni CH3 – NH2 + 2 H2O

Nitrobenzene is reduced to aniline

NO2 NH2

Pt + H2O
+ H2
4) Metal hydride reduction ( LiALH4)
Nitroalkanes are reduced to primary amines

CH3 – NO2 + H LiAlH4 CH3 – NH2 + 2 H2O

Nitrobenzene is reduced to azobenzene

NO2

+ H LiAlH4 + H2 O
5) Reduction in alkaline medium
Nitrobenzene gives different products during reduction in alkaline medium using
different reagents
+ 4 H2O
Zn / NaOH (aq.)

hydrazobenzene
NO2
Zn / NaOH in CH3OH + 4 H2O

Na3AsO3/ NaOH (aq.)


+ 3 H2 O
azoxybenzene
5) Electrolytic reduction
Nitrobenzene gives aniline in weakly acidic medium but gives p-aminophenol in
strongly acidic medium
NH2
weak acid
NO2

NHOH
strond acid rearrangement

N-phenylhydroxylamine p-aminophenol
5) Electrophilic substitution reaction in nitrobenzene

Halogenation O2 N
Cl
Cl2 / anhyd. FeCl3

Sulphonation ON
NO2 2
Conc. H2SO4 SO
H3

Nitration 100 C O2 N
NO
Conc. H2SO4, Conc. HNO3 2

NO2
Nitration 100 C
Conc. H2SO4, fumming HNO3

O2N NO2

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