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(A) The reaction sequence is as follows:$1$. $p$-Toluidine reacts with acetic anhydride in the presence of pyridine to form $N$-(p-tolyl)acetamide (co

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$2$-bromo-$4$-methylaniline

Vedclass · Answer

(A) The reaction sequence is as follows:$1$. $p$-Toluidine reacts with acetic anhydride in the presence of pyridine to form $N$-(p-tolyl)acetamide (compound $A$).$2$. Compound $A$ undergoes electrophilic aromatic substitution with $Br_2$ in $CH_3COOH$. The acetamido group $(-NHCOCH_3)$ is ortho/para directing. Since the para position is occupied by a methyl group,bromine enters the ortho position relative to the acetamido group to form $2$-bromo-$4$-methylacetanilide (compound $B$).$3$. Finally,acid-catalyzed hydrolysis $(H^{\oplus}/H_2O)$ of the acetamido group in compound $B$ yields $2$-bromo-$4$-methylaniline (compound $C$).

$C$ will be

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