Why does acetylation of $-NH_2$ group of aniline reduce its activating effect?

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) The activating effect of the $-NH_2$ group is due to the lone pair of electrons on the nitrogen atom,which is available for donation to the benzene ring through resonance,thereby increasing the electron density at the ortho and para positions.
When aniline is acetylated to form acetanilide $(C_6H_5NHCOCH_3)$,the lone pair of electrons on the nitrogen atom participates in resonance with the carbonyl group $(C=O)$. This delocalization of the lone pair towards the oxygen atom reduces its availability for donation to the benzene ring.
Consequently,the electron-donating power of the nitrogen atom towards the benzene ring is decreased,which reduces the activating effect of the group. This is represented by the following resonance structures:
$[:N-C(=O)-CH_3 \longleftrightarrow N^+=C-O^- -CH_3]$

Explore More

Similar Questions

What is the product $(X)$ in the reaction $C_6H_5NH_2 + HCl + NaNO_2 \rightarrow (X)$?

The reaction of cyclohexanone with dimethylamine in the presence of a catalytic amount of an acid forms a compound if water is continuously removed during the reaction. The compound formed is generally known as:

Which of the following can form intermolecular $H$-bond?

The compound $X (C_{7}H_{9}N)$ reacts with benzene sulphonyl chloride to give $Y (C_{13}H_{13}NO_{2}S)$ which is insoluble in alkali. The compound $X$ is

The major product $B$ in the following reaction sequence is:
$CH_3-CH_2-CH(CH_3)-CONH_2$ $\xrightarrow{Br_2/KOH, \Delta} (A)$ $\xrightarrow{(1) CH_3I (excess), (2) AgOH/\Delta} (B)$

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