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2 R N C CH
3
H
2
o
amide
+
2
o
amine
R N H
R
Cl C CH
3
2 R N C CH
3
R
3
o
amide
+ HCl
+ HCl
Reaction with acid anhydride
acid anhydride
+ CH
3
CH
+
2
o
amine
R N H
R
CH
3
C C CH
3
acid anhydride
R N C CH
3
R
3
o
amide
+ CH
3
CH
Reaction with ben!enesul"honyl chloride
Hinsber#$s test
+
NaN
2
& HCl
cold
NaCl
H
2
+
arenediazonium salt
.rimary
ali"hatic
amines
2orm a mi6ture of al!enes&
alcohols& al!yl halides and
nitro#en #as.
3econdary
ali"hatic
amines
2orm secondary "-
nitrosamines as yello# oil&
which is stable under the
reaction conditions.
1 ali"hatic amines and 2 ali"hatic amines
Reaction with bromine water
-niline reacts with a$ueous bromine to
yield #hite precipitates
"H
2
#rou" is an acti%ating and ortho-
para directors group
+
NH
2 NH
2
'r
'r
'r
3'r
2
(a*)
room tem"erature
3H'r
(2&/&7-tribromoaniline)
bservation, 8hite "reci"itate formed
1dentification
test
2ormation of dye
.rimary arylamines react with nitrous acid
to #ive arenedia!onium salts which are
stable at & C
-renedia!onium salts also under#o coupling
reaction with aromatic com"ounds with
stron# electron donatin# #rou"& such as 9H
and 9NR
2
at the para "osition to yield a!o
com"ounds
-!o com"ounds are usually intensely
coloured and relatively ine6"ensive
com"ounds& they are used as dyes
N N "
:
-
+
OH
N!N
N
(oran'e)
OH
CH
(
CH
(
N!N
()ellow)
N
CH
(
CH
(