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(A)

(B)

(C)
 
(D)

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Last updated date: 22nd Feb 2024
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Hint: Aniline is an organic compound in which $N{{H}_{2}}$ group is attached to a benzene ring. It is also known as phenylamine. This compound gets dark when exposed to air and light. It is a highly toxic compound. The behaviour of aniline is somewhat similar to that of primary aliphatic amines. It boils at a temperature of ${{183}^{o}}C$.

Complete Step by Step Answer:
Aniline and $HN{{O}_{2}}$ combine in the first step to produce diazonium salt, which is then combined with hydrogen fluoride ($HF$) and fluoroboric acid ($B{{F}_{3}}$) to create fluoro benzene ($PhF$). Fluorobenzene is a colourless liquid having the molecular formula ${{C}_{6}}{{H}_{5}}F$. It is also known as phenyl fluoride. It is a flammable substance.

Correct Option: (D) $Ph-F$.

Additional Information: The reagent, nitrous acid ($HN{{O}_{2}}$), which is used to convert aniline to diazonium salt, is prepared by the reaction of sodium nitrite ($NaN{{O}_{2}}$) and hydrochloric acid ($HCl$). The diazonium salt formed is unstable at room temperature and is usually prepared at a very low temperature (${{0}^{o}}-{{5}^{o}}C$). Diazonium salts, in general, are high-energy substances that can violently break down when heated or forced mechanically (shock-sensitive). It is an important intermediate for producing substituted benzene.

Note: Aniline is a highly used compound in the clothing industry. It is used as a dyeing agent. For the manufacturing of rubber chemicals and goods like automobile tyres, balloons, gloves, etc., anilines are employed in the rubber industry. Insecticide and reagents for plastic and resin polymers are uses of fluorobenzene.