Question

Explain the following observations: (a) Acetanilide is not soluble in HCl (b) Acetanilide answer carbylamine test only on prolonged heating ​

Answer 1

Answer:

aniline, the nitrogen atom donates its lone pair to the acid and by forming a salt (ionic compound), it dissolves in water(aqueous HCl). ... That's why acetanilide is not soluble in aqueous HCl

Answer 2

(a) Acetanilide is unable to transfer its single electron pair to HCl.

(b) Acetanilide is not an amine (or primary amine either) to directly answer the test positively and therefore needs to undergo decomposition.

• Like aniline, acetanilide is unable to give its single pair of electrons to HCl.
• Here, no ionic salt is created, and as a result, there is no aqueous solvent dissolving.
• Because of this, acetanilide does not dissolve in aqueous HCl.
• Chemical tests for the identification of primary amines include the carbylamine reaction, sometimes referred to as the Hofmann's isocyanide test.
• A primary amine will result in the formation of the unpleasant-smelling isocyanide (carbylamine).
• Prolonged heating ​of Acetanilide causes it to undergo decomposition.
• Therefore, only after decomposition, Acetanilide can answer the carbylamine test or otherwise it does not answer the test.

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