Name: Introduction to Diazonium Salts
Uploaded: 2019-07-19
Duration: 4 min 11 s
Description: Diazonium salts are one of the most important classes of amines that are useful both in the laboratory and in the commercial world. Watch this video to learn...

Question

How to convert Aniline into Benzoic acid and Benzoic acid into Aniline.

Accepted Answer

Convert Aniline into Benzoic acid:

Benzenediazonium chloride is prepared by the reaction of aniline with nitrous acid at $273 - 278 K$ . Nitrous acid is produced in the reaction mixture by the reaction of sodium nitrite with hydrochloric acid. The conversion of primary aromatic amines into diazonium salts is known as diazotisation.
$C_{6} H_{5} {NH}_{2} \overset{{NaNO}_{2} / HCl}{\to} C_{6} H_{5} N_{2} Cl$
Reaction between diazonium Chloride and $CuCN$ to form phenyl cyanide. This reaction is called Sandmeyer reaction.

$C_{6} H_{5} N_{2} Cl \overset{CuCN}{\to} C_{6} H_{5} CN$

Hydrolysis of the benzonitrile to form benzoic acid.

$C_{6} H_{5} CN \overset{H_{3} O^{+}}{\to} C_{6} H_{5} COOH$

And Convert Benzoic Acid to Aniline

Reaction between benzoic acid and Ammonia under the presence of heat to form benzamide.

$C_{6} H_{5} COOH \overset{{NH}_{3} / Heat}{\to} C_{6} H_{5} {CONH}_{2}$

Hoffmann developed a method for preparation of primary amines by treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide to form aniline.
$C_{6} H_{5} {CONH}_{2} \overset{{Br}_{2} / NaOH}{\to} C_{6} H_{5} {NH}_{2}$

How to convert Aniline into Benzoic acid and Benzoic acid into Aniline.

Important Questions on Organic Compounds Containing Nitrogen

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