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Preparation of p-nitroacetanilide, hydrolysis of p-nitroacetanilide, preparation of p-nitroaniline (Student's Handout)

Preparation of p-nitroacetanilide, hydrolysis of p-nitroacetanilide, preparation of p-nitroaniline (Student's Handout)

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Published by Dotsha Raheem
p-nitroacetanilide, p-nitroaniline, nitration of acetanilide, hydrolysis of p-nitroacetanilide, preparation of p-nitroaniline
p-nitroacetanilide, p-nitroaniline, nitration of acetanilide, hydrolysis of p-nitroacetanilide, preparation of p-nitroaniline

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Published by: Dotsha Raheem on Apr 11, 2010
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Preparation of p-nitroaniline
Student’s Handout
Week (1): Preparation of p-nitroacetanilideWeek (2): Hydrolysis of p-nitroacetanilideDotsha J. RaheemUniversity of SalahaddinCollege of Science – Department of ChemistryApril - 2010
1
 
1.Preparation of p-nitroacetanilide (nitration oacetanilide)
Aniline cannot be nitrated with the usual nitrating mixture of nitricand sulphuric acid, because charring and oxidation of aniline. Thedifficulty may be overcome either by using a very large excess of sulphuric acid, or (better) by protecting the reactive amino group byacetylation (write chemical reaction), since the acetylamido group,CH
3
CONH-, has the same ortho and para directing influence as the NH
2
-group itself. Acetanilide undergoes ready nitration, giving chiefly thecolorless p-nitroacetanilide, mixed with a much smaller proportion of theyellow o-nitroacetanilide. Recrystallization from ethanol readily removesthe more soluble ortho compound, and the pure p-nitroacetanilide canthen be hydrolyzed to p-nitroaniline.
NH
2
Aniline+HNO
3
/ H
2
SO
4
NH
3
Anilinium ionHNO
3
H
2
SO
4
metasubstitutionCharring and oxidationof aniline
 The overall reaction for the preparation of p-nitroaniline can beexplained in the following steps:
1.Protection of the amino group
NH
2
Aniline+CH
3
OH
3
COOAcetic anhydrideH
3
COOHCH
3
HNOAcetanilideH
3
COOH+Acetic acid
2
 
2.
Nitration of acetanilide
CH
3
HNOAcetanilideHNO
3
/ H
2
SO
4
CH
3
HNOCH
3
HNO+NO
2
NO
2
o-nitroacetanilidep-nitroacetanilide"Major product"
3.Hydrolysis of p-nitroacetanilide
CH
3
HNONO
2
p-nitroacetanilide1) HydrolysisH
+
, H
2
O2) OHNH
2
NO
2
p-nitroaniline
The whole experiment will be covered in two weeks:
Week 1: Preparation of p-nitroacetanilide
MECHANISM OF THE REACTION
1.
Generation of the nucleophile (nitronium ion)
HNO
3
+2 H
2
SO
4
NO
2
+H
3
O+2 HSO
4
3

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