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Preparation of Acetanilide
O
O
NH2 O O HN CH3
O
H3C OH
+ H3C O CH3 + H3C OH
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?