Question: Aniline first reacts with acetyl chloride producing compound ‘A’. ‘A’ reacts with the \(\text{ nitri...

Question

Aniline first reacts with acetyl chloride producing compound ‘A’. ‘A’ reacts with the $\text{ nitric acid/sulphuric acid}$ and produces compound ‘B’, which hydrolyses to compound ‘C’. What is the identity of ‘C’?
A.Acetanilide
B. $p - \text{Nitroacetanilide}$
C. $p - \text{Nitroaniline}$
D.Aniline

Answer 1

Solution

At first we will need to know the chemical formula and reaction between aniline and acetyl chloride to find ‘A’. When we find ‘A’ we will perform a nitrogenation reaction with acid to find the ‘B’. After finding ‘B’ we will perform hydrolysis to remove the acid and find the final product.

Complete step by step solution:
In the given question we have to follow the step by step analysis of the steps conducted so that we can get to the final product obtained and meanwhile get the products in between.
So the step by step process of the mentioned reaction will be as follows:
Step1: Our target is to find A. This reaction between Aniline and acetyl chloride will remove the $HCl$ and will form an Acetanilide. The chemical formula of Acetanilide is ${C_6}{H_5}NHCO{C_6}{H_5}$ .
Step2: Now in the next step we will see the rearrangement and the displacement of the second benzyl ring by the $Conc.HN{O_3}$ which will yield $o -\text{nitroacetanilide}$ as the product which is having chemical formula of ${C_6}{H_5}(N{O_2})NHCOC{H_3}$ .
Step3: now in the final product would be the generation of the carboxylic acid as the byproduct due to the aqueous medium. This will give the base in the product as the ortho and para substitutions due to the nature of the ring. So the final product will be the $p -\text{ Nitroaniline}$ and $o -\text{ Nitroaniline}$ .
So this gives us the correct option as the option $p -\text{Nitroaniline}$ .

Hence, the correct answer is option C.

Note: The term nitroaniline in chemistry refers to a derivative of aniline $({C_6}{H_5}N{H_2})\;$ containing a nitro group $(-N{O_2})$ There are three simple nitroanilines of formula ${C_6}{H_4}(N{H_2})(N{O_2})$ which differ only in the position of the nitro groupSome more complicated molecules with other substituents can also be referred to as nitroanilines, for example 4-chloro-3-nitro-aniline.