Question

Identify X in the series,

$\xrightarrow[\text{H}_2\text{SO}_4]{\text{HNO}_3}$ Intermediate $\xrightarrow[\Delta]{\text{H}_2\text{O}}X$:

Answer 1

X is a mixture of ortho-nitroaniline and para-nitroaniline, with para-nitroaniline being the major product due to steric hindrance.

Answer 2

The reaction starts with acetanilide, which undergoes nitration using $\text{HNO}_3/\text{H}_2\text{SO}_4$. The $-\text{NHCOCH}_3$ group is an activating group and an ortho, para director, leading to nitration at both positions. Para-nitroacetanilide is the major product due to steric hindrance.

Hydrolysis of the intermediate (a mixture of ortho-nitroacetanilide and para-nitroacetanilide) with water and heat cleaves the amide bond, forming an amine and a carboxylic acid. This yields ortho-nitroaniline and acetic acid from ortho-nitroacetanilide, and para-nitroaniline and acetic acid from para-nitroacetanilide.

Therefore, X is a mixture of ortho-nitroaniline and para-nitroaniline, with para-nitroaniline as the major product.