Which of the following statements relating to aniline is not...

Which of the following statements relating to aniline is not true? (a) aniline on Schotten-Baumann reaction gives benzanilide (b) aniline cannot be prepared by the reduction of benzonitrile with $\mathrm{LiAlH}_{4}$ (c) on heating with concentrated $\mathrm{H}_{2} \mathrm{SO}_{4}$ at $180^{\circ} \mathrm{C}$, aniline gives sulphanilic acid (d) aniline liberates nitrogen on treatment with ice cold nitrous acid

Which of the following statements relating to aniline is not true?
(a) aniline on Schotten-Baumann reaction gives benzanilide
(b) aniline cannot be prepared by the reduction of benzonitrile with $\mathrm{LiAlH}_{4}$
(c) on heating with concentrated $\mathrm{H}_{2} \mathrm{SO}_{4}$ at $180^{\circ} \mathrm{C}$, aniline gives sulphanilic acid
(d) aniline liberates nitrogen on treatment with ice cold nitrous acid

Key Concepts

Schotten-Baumann Reaction

This is a technique for the acylation of amines that involves reacting an amine with an acid chloride under basic, usually aqueous, conditions. It is used to form amides such as benzanilide from aniline by reacting it with benzoyl chloride.

Reduction of Nitriles with Lithium Aluminium Hydride

This concept deals with the chemical reduction of nitrile groups to primary amines using LiAlH4. In the context of aromatic compounds, however, the reduction of a benzonitrile leads to a different structure than aniline, emphasizing that the reduction pathway does not yield the expected aromatic amine directly.

Aromatic Sulfonation

This refers to the electrophilic aromatic substitution reaction in which a sulfonic acid group is introduced onto an aromatic ring. The reactivity of aniline in sulfonation is affected by the amino group; under strongly acidic conditions the amino group is protonated, which deactivates the ring, and may lead to unusual or less efficient sulfonation compared to its protected derivatives.

Diazotization of Aromatic Amines

This reaction involves treating an aromatic amine with nitrous acid under cold conditions to form a diazonium salt. The process is typically carried out under ice-cold conditions to stabilize the diazonium intermediate, and does not involve the liberation of nitrogen gas at low temperature, which is a key distinction from the behavior of aliphatic amines in similar reactions.

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