IMO Practice Test — Amines

Three bottles X, Y, Z contain a 1°, 2° and 3° amine. On the Hinsberg test, X gives a KOH-soluble solid, Y gives a KOH-insoluble solid, Z gives no reaction. The correct identification is:

An amine C₃H₉N gives N₂ gas with HNO₂ and is positive in the carbylamine test. The number of structural isomers fitting this description is:

Aniline is treated with (i) (CH₃CO)₂O, then (ii) Br₂, then (iii) hydrolysis. The final major product is:

Which sequence converts benzene to fluorobenzene?

The compound that does NOT evolve a gas on treatment with NaNO₂/HCl at 5°C is:

Increasing order of basic strength: aniline (I), p-nitroaniline (II), p-methylaniline (III). Correct order is:

An amide R–CONH₂ on Hofmann degradation gives a 1° amine with 4 carbons. The amide was:

Why does the diazonium salt couple with phenol but only feebly with benzene?

A primary amine A (C₂H₇N) on reaction with CHCl₃/KOH gives B with a foul smell. B is:

To prepare benzonitrile from aniline, the correct reagents in order are:

Among CH₃NH₂, (CH₃)₂NH, (CH₃)₃N and NH₃, which is the weakest base in aqueous solution?

The reagent that converts a diazonium salt to phenol is:

A 1° amine has a higher boiling point than its 3° isomer mainly because:

Methyl orange, an azo indicator, is made by coupling a diazonium salt with: