Which one of the following products is obtained on treatment of aniline with nitrous acid?
Which one of the following products is obtained on treatment of aniline with nitrous acid?
Nitrobenzene
Phenol
Benzene diazonium salt
benzene
The Correct Option is C
Solution and Explanation
When aniline (C6H5NH2) is treated with nitrous acid (HNO2), it forms benzene diazonium salt. This reaction is known as diazotization and is an essential step in the preparation of azo dyes. The nitrous acid required for this reaction is typically generated in situ by mixing sodium nitrite (NaNO2) with a mineral acid like hydrochloric acid (HCl). The reaction occurs at low temperatures (0-5°C) due to the instability of the diazonium compound formed. The balanced chemical equation for the reaction is:
C6H5NH2 + HNO2 + HCl → C6H5N2Cl + 2H2O
Here, C6H5N2Cl is benzene diazonium chloride, the benzene diazonium salt. This process illustrates how aniline, when exposed to nitrous acid, undergoes a transformation to yield a diazonium salt, a crucial intermediate in synthetic organic chemistry, particularly in dye manufacturing. Therefore, the correct answer is benzene diazonium salt.
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Concepts Used:
Organic Chemistry – Some Basic Principles and Techniques - Reaction Mechanism
SN1 Reaction Mechanism:
SN1 reaction mechanism takes place by following three steps –
- Formation of carbocation
- Attack of nucleophile
- Deprotonation
SN2 Reaction Mechanism:
The SN2 reaction mechanism involves the nucleophilic substitution reaction of the leaving group (which generally consists of halide groups or other electron-withdrawing groups) with a nucleophile in a given organic compound.
Electrophilic Aromatic Substitution Reaction Mechanism:
The mechanism of an electrophilic aromatic substitution reaction contains three main components which are:
- A new sigma bond from C=C is formed during the reaction in the arene nucleophile.
- Due to the breaking of the C-H sigma bond, a proton is removed.
- The C=C bond is reformed and it restores the aromaticity of the compound.
Electrophilic Substitution Reaction Mechanism:
The electrophilic substitution reaction mechanism is composed of three steps, which will be discussed more below.
- Electrophile Generation
- Carbocation Formation
- Proton Removal