Experiment O04 Preparation of Aniline

Chemicals: Nitrobenzene (4 cm3), granulated tin (10 g), conc. hydrochloric acid (35 cm3), approx. 30% a ueou! Na"# !olution (50 cm3), ether (15 cm3), !odium hydroxide pellet! (5 g), litmu! paper (blue and red) pota!!ium hydroxide pellet! (5 g). ($or !econd practical !e!!ion)

Apparatus: 10 cm3 mea!uring cylinder, %5 cm3 mea!uring cylinder, %50 cm3 round&bottomed $la!', 1000 cm3 (ater&bath, )iebig (ater conden!er, !cre(&cap adaptor, rubber tubing adaptor, !eparating $unnel, %*150 cm3 bea'er!, 100 cm3 conical $la!' and !topper, 50 cm3 round&bottomed $la!', 100 cm3 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 cm3 o$ nitrobenzene and 10 g o$ tin in a %50 cm3 round&bottomed $la!' $itted (ith a re$lux conden!er. .dd exce!! concentrated hydrochloric acid, by adding it to the $la!' a $e(

cm3 at a time, until a total o$ %4 cm3 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 cm3 o$ acid !hould be needed) and, (hen cool, tran!$er the !olution to the !eparating $unnel. 5xtract (ith t(o !eparate 5 cm3portion! o$ 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 cm3 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 195o+ and record the yield.

5ther di!tillation

7i!tillation o$ aniline -.4

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)

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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 cm3 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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