Acetanilide on nitration followed by alkaline | vedclass

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Question

(B) The nitration of acetanilide $(C_6H_5NHCOCH_3)$ is an electrophilic aromatic substitution reaction. The acetamido group $(-NHCOCH_3)$ is strongly

Vedclass · Accepted Answer

$p-$Nitroaniline

Vedclass · Answer

(B) The nitration of acetanilide $(C_6H_5NHCOCH_3)$ is an electrophilic aromatic substitution reaction. The acetamido group $(-NHCOCH_3)$ is strongly activating and ortho/para-directing. Due to the steric hindrance of the bulky acetamido group,the para-isomer is the major product.$1$. Nitration of acetanilide with $conc. HNO_3 / H_2SO_4$ yields $p-$nitroacetanilide as the major product.$2$. Subsequent alkaline hydrolysis of $p-$nitroacetanilide removes the acetyl group to yield $p-$nitroaniline.The reaction sequence is:$C_6H_5NHCOCH_3$ $\xrightarrow{HNO_3/H_2SO_4} p-NO_2-C_6H_4-NHCOCH_3$ $\xrightarrow{OH^-/H_2O} p-NO_2-C_6H_4-NH_2$.

Acetanilide on nitration followed by alkaline hydrolysis mainly gives-

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