Experiment O04 Preparation of Aniline

Chemicals: Nitrobenzene (4 cm
3
),
granulated tin (10 g),
conc. hydrochloric acid (35 cm
3
),
approx. 30% aueou! Na"# !olution (50 cm
3
),
ether (15 cm
3
),
!odium hydroxide pellet! (5 g),
litmu! paper (blue and red)
pota!!ium hydroxide pellet! (5 g). ($or !econd practical !e!!ion)

Apparatus: 10 cm
3
mea!uring cylinder,
%5 cm
3
mea!uring cylinder,
%50 cm
3
round&bottomed $la!',
1000 cm
3
(ater&bath,
)iebig (ater conden!er,
!cre(&cap adaptor,
rubber tubing adaptor,
!eparating $unnel,
%*150 cm
3
bea'er!,
100 cm
3
conical $la!' and !topper,
50 cm
3
round&bottomed $la!',
100 cm
3
round&bottomed $la!',
air conden!er,
thermometer poc'et,
%50
o
+ thermometer,
,un!en burner, tripod and gauze.
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Experiment O04 Preparation of Aniline
Procedure:
a. Reduction of nitrobenzene
-lace 4 cm
3
o$ nitrobenzene and 10 g o$ tin in a %50 cm
3
round&bottomed $la!' $itted (ith a
re$lux conden!er. .dd exce!! concentrated hydrochloric acid, by adding it to the $la!' a $e(
cm
3
at a time, until a total o$ %4 cm
3
ha! been added. /t i! mo!t con0enient to pour the acid
do(n the conden!er, and it i! ad0i!able to !ha'e the $la!' bet(een each addition. 1hen all
the acid ha! been added heat the reaction mixture on a (ater&bath $or 15 minute!.
2e$lux
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Experiment O04 Preparation of Aniline
b. Steam distillation
+ool the $la!' and add !odium hydroxide !olution until the !olution i! !trongly al'aline. 3he
hydroxide o$ tin, (hich i! precipitated $ir!t, !hould be di!!ol0ed (about 50 cm
3
o$ 30%
!odium hydroxide !olution !hould be !u$$icient)
4et up the apparatu! $or !team di!tillation and proceed until oily droplet! o$ aniline are no
longer 0i!ible in the di!tillate coming o0er.
4team di!tillation
c. Ether extraction
.dd concentrated hydrochloric acid to the di!tillate, until the !olution i! acidic (about 3 or 4
cm
3
o$ acid !hould be needed) and, (hen cool, tran!$er the !olution to the !eparating $unnel.
5xtract (ith t(o !eparate 5 cm
3
portion! o$ ether. .$ter !ha'ing the !eparating $unnel, in0ert
the $unnel and open the tap to relea!e the ether 0apour. iscard the ether la!er in each
case (run it into the ether re!idue! bottle).
3ran!$er the a"ueous la!er to a bea'er and add !odium hydroxide pellet!, one at a time,
until the !olution i! al'aline.
4ha'e thi! al'aline !olution, in a !eparating $unnel, (ith 5 cm
3
portion! o$ ether. Retain the
ether la!er $rom thi! !eparation. (6ir!t practical !e!!ion $ini!hed)
7ry the ethereal extract, by !tanding it o0er 5g pota!!ium hydroxide pellet!, in a !toppered
$la!' until the next practical !e!!ion.
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Experiment O04 Preparation of Aniline
d. Ether distillation and distillation of aniline
#eat a (ater bath to about 80
o
+ and, a$ter extingui!hing all $lame!, decant the ethereal
!olution into a 50 cm
3
round&bottomed $la!' $itted (ith a !cre(&cap adaptor and (ater
conden!er. #eat the $la!' in the (ater bath until no more ether di!til!.
2eplace the (ater conden!er by an air conden!er, $it a thermometer poc'et and %50
o
+
thermometer to the !cre(&cap adaptor and heat the $la!' o0er a gauze u!ing a ,un!en
burner. +ollect the $raction (hich di!til! bet(een 190
o
+ and 195
o
+ and record the yield.
5ther di!tillation
7i!tillation o$ aniline
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Experiment O04 Preparation of Aniline
Name:
4eat No.:
7ate:
;ield o$ aniline <
=rade:
#uestions:
1. 1hy mu!t the !olution be made al'aline be$ore !team di!tillation> (-rocedure b)




%. 1hy i! the reaction mixture cooled be$ore the addition o$ !odium hydroxide in part b.
(-rocedure b)


3. 1hy i! hydrochloric acid added to the di!tillate be$ore the $ir!t ether extraction and (hy i!
thi! ethereal !olution di!carded> (-rocedure c)





4. 1hy i! !odium hydroxide added be$ore the !econd ether extraction and (hy i! thi! ethereal
!olution retained> (-rocedure c)


5. 1hy are t(o !eparate 5 cm
3
portion! o$ ether u!ed in -rocedure c, rather than one 10 cm
3
portion>




?. 1hy i! pota!!ium hydroxide u!ed $or drying aniline, rather than the cheaper calcium
chloride>



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