Question

Which product of the following reactions fails to give carbylamine test?

• A. Hoffmann-bromamide degradation
• B. Gabriel phthalimide synthesis
• C. Reduction of nitrites with LiAlH ${}_4$
• D. Reduction of tertiany amides with LiAlH ${}_4$

Answer 1

Answer: (D)

Carbylamine test is also known as Hofmann's isocyanide test, it is used for detection of primary amines. If primary amine is present it forms carbylamine (isocyanide) and gives foul smelling substance. Since, on reduction of tertiary amide with LiAlH ${}_4$ no primary amine is obtained as product, so carbyl amine test fails.