Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid.

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Solution

(i) Aromatic primary amines react with nitrous acid at low temperatures (273-278K) to form diazonium salts.

$C_{6} H_{5} - N H_{2} A n i l i n e N a N o_{2} + H C l - ------- \to 273 - 278 K C_{6} H_{5} - {+ N}_{2} - C l B e n z e n e d i a z o n i u m c h l o r i d e + N a C l + 2 H_{2} O$

Note : Nitrous acid is produced by the reaction of NaNO_2 and HCl

(ii) Aliphatic primary amines react with nitrous acid to form aliphatic diazonium salts (unstable), which produce nitrogen gas and alcohols after decompostion.

$R - N H_{2} + H N O_{2} A l k y l a m i n e N a N o_{2} + H C l - ------- \to [R - {+ N}_{2} - C l] B e n z e n e d i a z o n i u m c h l o r i d e H_{2} O - - \to R O H A l c o h o l + N_{2} + H C l$

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Give plausible explanation for each of the following:

(i) Why are amines less acidic than alcohols of comparable molecular masses?

(ii) Why do primary amines have higher boiling point than tertiary amines?

(iii) Why are aliphatic amines stronger bases than aromatic amines?

Some statements are given about acylation of amines with acid chloride

I. Tertiary amines do not react with acid chloride

II. This reaction is an example of a nuclophilic addition reaction

III. This reaction is carried out in the presence of pyridine

IV. Aliphatic and aromatic primary and secondary amines involve in this reaction

The correct statements is/ are

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