before reacting aniline with HNO3 for nitration it is converted to acetanilide. why
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Aniline is highly activated towards electrophilic aromatic substitution. However, aniline is also a base. Once protonated, the anilinium ion is formed which is a strong deactivator and a meta director. This nitrogen basicity makes the direct nitration of aniline impossible. One solution to the problem is to use an acetyl group (CH3CO) to “protect” the nitrogen atom during the nitration by converting the amine to an amide. After nitration, the amide protecting group may be removed by hydrolysis. The process involves a three-step sequence of chemical reactions called “protection-nitration-deprotection.”
1. Protection of the amine to form the amide.
2. Nitration of the aromatic ring.
3. Deprotection by hydrolysis of the amide to reform the amine.
aniline acetanilide p-nitroacetanilide p-nitroaniline.
1. Protection of the amine to form the amide.
2. Nitration of the aromatic ring.
3. Deprotection by hydrolysis of the amide to reform the amine.
aniline acetanilide p-nitroacetanilide p-nitroaniline.
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Hey folk...
Since Aniline is too much reactive towords electrophilic substitution , and when it is protonated it get converted to anilinium ion, and the ion formed is ring deactivating and meta directing too.
The direct nitration is impossible bcoz of high basisity of Aniline.
This is the reason anailine is converted into acetanilide to decrease it's reactivity wid reaction with HNO₃.
HOPE IT HELPS...
#Mme
Since Aniline is too much reactive towords electrophilic substitution , and when it is protonated it get converted to anilinium ion, and the ion formed is ring deactivating and meta directing too.
The direct nitration is impossible bcoz of high basisity of Aniline.
This is the reason anailine is converted into acetanilide to decrease it's reactivity wid reaction with HNO₃.
HOPE IT HELPS...
#Mme
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