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 Preparation of Acetanilide

O
O
NH2 O O HN CH3
O
H3C OH
+ H3C O CH3 + H3C OH

Aniline Acetic anhydride Acetic acid


Acetanilide
$ Nitration of Acetanilide
O O
O
CH3 HN CH3
HN HN CH3
HNO3 / H2SO4 NO2
+

Acetanilide NO2

o-nitroacetanilide p-nitroacetanilide
"Major product"
ï Hydrolysis of Acetanilide

H H H
1) Hydrolysis
H ,H

) H

-nitroacetanilide -nitroaniline
_
   

m-director
o,p-director à à
à   




 à


 








So, acetylation



protects aniline from
protonation, charring
and oxidation
¯his lab.:

c ta ili
- itr ac ta ili - itr ac ta ili
" a r r ct"
Æ ô ¯he major product is para,
but why not ortho?

ô ¯his is mainly due to steric


effect.
ortho-nitroacetanilide para-nitroacetanilide
ortho-nitroacetanilide para-nitroacetanilide
Notes on the Experiment
ô Nitration of acetanilide is an exothermic
reaction ; the temperature must be carefully
controlled by chilling, stirring, and the slow
addition of reagents.

ô ¯he reaction is conducted below 0Û C to


maintain selectivity by preventing less
favorable reactions from occurring [o- and 2,4-
dinitro products require higher energy]
Notes on the Experiment
ô Glacial acetic acid is used because it is a polar
solvent capable of dissolving acetanilide, and
the acetate ion is a poor nucleophile so no
substitution is possible.

ô A mixture of concentrated nitric and sulfuric


acids is used as the nitrating mixture.
Notes on the Experiment
ô ¯o prevent dinitration of the acetanilide, the
nitrating mixture is added in small portions to
the acetanilide solution (and not vice versa) so
that the concentration of HNO3 is kept at a
minimum.

ô After the addition is complete the beaker is


allowed to stand at room temperature for 30
minutes [more than that will lead to the
formation of 2,4-dinitroacetanilide].
Notes on the Experiment

ô o-nitroacetanilide has higher solubility in the


aqueous solution than p-nitroacetanilide.

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