Why is $-NH_2$ group of aniline acetylated before carrying out nitration?

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) Direct nitration of aniline yields tarry oxidation products in addition to the nitro derivatives.
In the strongly acidic medium used for nitration,aniline is protonated to form the anilinium ion $(-NH_3^+)$,which is meta-directing.
This leads to the formation of a significant amount of meta-nitroaniline along with ortho and para derivatives.
By protecting the $-NH_2$ group through acetylation with acetic anhydride,the reactivity of the amino group is reduced.
This prevents the formation of the anilinium ion and allows for the controlled nitration,making the $p$-nitroacetanilide the major product,which can then be hydrolyzed to $p$-nitroaniline.

Explore More

Similar Questions

The compound which on reaction with aqueous nitrous acid $(HNO_2)$ at low temperature produces an oily nitrosoamine is

Identify $X$ and $Y$ in the following reaction: ${C_6H_5NH_2}$ $\xrightarrow[0^{\circ} - 5^{\circ}C]{NaNO_2 + 2HCl} X$ $\xrightarrow[H_2O]{HNO_2} Y + N_2 + HCl$

Choose the correct option.

Difficult
View Solution

$CH_3-NH_2 \xrightarrow{HNO_2} ?$

Benzylamine is a stronger base than aniline because

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo