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hydrolysis of p-nitroacetanilide,
preparation of p-nitroaniline
(Student's Handout)
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H
N
CH 3
O
+
o-
HN
HN
NO 2
CH 3
CH 3
HN
HN
O
NO 2
CH 3
O
?
Resounance structures
NO 2
3. Deprotonation
CH 3
HN
CH 3
HN
NO 2
H
HSO 4
H
HSO 4
NO 2
H 2SO 4
H 2SO 4
o-nitroacetanilide
CH 3
HN
O
NO 2
CH 3
HN
O 2N
p-nitroacetanilide
O
NO 2
H
HN
O
NO 2
H
p- attach
HN
NO 2
NO 2
p-
CH 3
CH 3
CH 3
o- attach
O
H 3C
NH
1) H / H 2O
NH 2
2) OH
NO 2
p-nitroacetanilide
NO 2
p-nitroaniline
O
+
N
O
3.p-nitroacetanilide
Prepare a solution of concentrated nitric acid 2.0 ml and
H 3C
concentrated
sulfuric acid 1.5ml. H3C C OH
H3 C
-
C OH
O H
H
OH
C
+
+
NH
N
NHfunnel
4.N+ Add drop
wise (use dropping
or pipette)
theNH
N
O
O
O
nitric/sulphuricOmixture to the acetanilideHSO
(not
the reverse).
4
H of
H addition so that the temperature does not
Adjust the rate
rise above 10 o C.
-
O
H
O
5.N+ After theNHaddition
is complete allow
the beaker to stand at
+
+
2
N
NH 3 HSO 4
OH
H 3C
O
room temperature for 30 minutes.O
or
CH 3COO
6. Pour the- contents of the flask into 150g of crushed ice. [the
H 2O
O
NaOH
+
o-nitroacetanilide,
being
soluble,
in solution while p+
N
NH 2
NaHSOremains
4
O
CH 3 COONa
nitroacetanilide precipitates out]
7. Filter the solid on a Bchner funnel.
SO4 in
2) OH
NOon
2
5. Cool and filter the
product
a Buchner
funnel. Wash it thoroughly with water.
NO 2crystalline
yellow
p-nitroacetanilide
p-nitroaniline
6
5
H 3C
O
+
N
O
O
NH
H 3C
O
+
N
O
C OH
NH
H 3C
O
+
N
O
C OH
NH
p-nitroacetanilide
H3 C
H3 C
O
+
N
O
C OH
NH
O
+
N
O
NH
NH 2
NaOH
O
+
N
O
H 3C
H 3C
O H
H
O
+
N
O
OH
C
NH
HSO 4
O
+
N
O
OH
C
OH
NH 2
O
+
N
O
NH 3
HSO 4
or
CH 3COO
H 2O
NaHSO 4
CH 3 COONa
SO4 in