Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

What is the product formed when picryl chloride reacts with ammonia? 

Options:

Picric acid 

2,4,6-Trinitroaniline 

Aniline 

No reaction

Correct Answer:

2,4,6-Trinitroaniline 

Explanation:

The correct answer is option 2. 2,4,6-Trinitroaniline.

When picryl chloride (2,4,6-trinitrochlorobenzene) reacts with ammonia \((NH_3)\), it undergoes a nucleophilic aromatic substitution \((S_NAr)\) reaction. In this reaction, the lone pair of electrons on the nitrogen atom of the ammonia molecule acts as a nucleophile attacking the electrophilic carbon atom bearing the chlorine atom in the picryl chloride molecule. This results in the substitution of the chlorine atom with an amino group \((NH_2)\). The reaction proceeds as follows:


The product formed is 2,4,6-trinitroaniline, which is an aromatic compound containing an amino group \((NH_2)\) substituted at the meta position to the three nitro groups \((-NO_2)\) on the benzene ring. The hydrogen chloride \((HCl)\) is a byproduct of the reaction.

The reaction involves the displacement of the chloride group by the nucleophilic ammonia molecule, resulting in the formation of an amine group on the benzene ring. This substitution reaction is characteristic of aromatic compounds containing electron-withdrawing groups, such as nitro groups, which make the carbon atoms on the benzene ring electron deficient and susceptible to nucleophilic attack.

In summary, when picryl chloride reacts with ammonia, the product formed is 2,4,6-trinitroaniline, along with the release of hydrogen chloride as a byproduct.