Chemistry Answer the following in one or two sentence.

(1) Aniline reacts with a Lewis acid, forms salt.
(2) Aniline does not undergo Friedcl-Crafr’s reaction (alkylation and acetylation) due to salt formation with aluminium chloride (Lewis acid), which is used as catalyst. Due to this, nitrogen of anime acquires + ve charge and hence acts as strong deactivating effect on the ring and makes it difficult for electrophilic attack.

In the laboratory, ammonolysis of alkyl halides is not a suitable method to prepare primary amines as it gives a mixture of primary, secondary, tertiary amines and quaternary ammonium salts.

Amines in an increasing order of boiling points : trimethyl amine, ethyl methyl amine, n-propyl amine

The alkyl group tends to increase the electron density on the nitrogen atom. As a result, amines can donate the lone f pair of electrons on nitrogen more easily than ammonia. Hence, aliphatic amines are stronger bases than ammonia.

2 moles of methylbromide are required to convert ethanamine to N, N-dimethyl ethanamine.

The product is aniline/

In Gabriel-phthalimide synthesis of aniline, potassium phthalimide requires the treatment with chlorobenzene or bromobenzene. Since aryl halides do not undergo nucleophilic substitution reaction. Therefore, chlorobenzene or bromobenzene does not react with potassium phthalimide to give N-phenylphthalimide and hence aniline cannot be prepared by Gabriel phthalimide synthesis.

Due to the presence of two H-atoms on N-atom in butait- I -amine, they undergo extensive intermolecular H-bonding while in N-cthylethanamine due to the presence of one-H atom on the N-atom, they undergo least intermolecular H-bonding. Hence, butan- l-amine has higher boiling point than-N-ethyl ethanamine.

Rutan- l-al is more soluble in watcr duc to intermoiccular hydrogen bonding. In alcohols, hydrogen bonding is through oxygen atoms. WIereas hutani-amine is less soluble in water due to the larger hydrocarbon part is hydrophobic in nature. Hence, butan-l-ol is more soluble in water than butani-amine.

When aniline is heated with acetic anhydride, an acetanilide is obtained.

When aniline is warmed with a mixture of cone, nitric acid and cone, sulphuric acid (a nitrating mixture), a mixture of ortho, meta and para nitroaniline is obtained.

Action of aqueous bromine on aniline : When aniline is treated with bromine water at room temperature, a white precipitate of 2, 4, 6-tri bromoaniline is obtained.

Ethylamine is an aliphatic amine, while aniline is an aromatic amine. So the two can be distinguished by the following test :

(1) When ethyl amine is treated with p-toluene sulphonyl chloride, N-ethyl p-toluene sulphonamide is obtained.


(2) When diethyl amine is treated with p-toluene suiphonyl chloride. N.N-dicthyl p-toluene suiphonyl amide is formed.

When fluoroboric acid is treated with the solution of diazonium salt, a precipitate of diazonium fluoroborate is obtained, which is filtered and dried. When dry diazonium fluoroborate is heated, it decomposes to give aryl fluoride. This reaction is called Balz-Schiemann reaction.

Benzenediazonium chloride is prepared by the action of nitrous acid on aniline at 273-278 K. Nitrous acid being unstable, is prepared in situ by the reaction between sodium nitrite and dilute hydrochloric acid.

Aniline reacts with nitrous acid in cold to form diazonium salt which has reasonable solubility at 273 K

Ethyl amine on reaction with nitrous acid in cold forms aliphatic diazonium salt, (unstable intermediate), which decomposes immediately by reaction with solvent water to produce ethyl alcohol and nitrogen gas.

When benzoyl chloride is treated with ethanamine, N-ethyl benzamide is obtained.

Aniline on reaction with acetic anhydride forms N-phenyl acetamide.

Benzylamine C6H5CH2NH2 on exhaustive methylation i.e., on heating with excess methyl iodide forms benzylmethyl amine, benzyldimethyl ammonium chloride and finally benzyltrimethyl ammonium iodide.

When acetamide is treated with bromine and aq or alcoholic solution of KOH, methyl amine is obtained, which has one cabon atom less.

Acid amides on reduction with lithium aluminium hydride or sodium, ethanol form corresponding primary amines.

For example : Acetamide on reduction with lithium aluminium hydride or sodium, ethanol gives ethylamines.

Methyl cyanide or acetonitrile on reduction by sodium and ethyl alcohol forms ethanamine. The reaction is called Mendius reduction.

Nitrobenzene is reduced to aniline by passing hydrogen gas in the presence of finely divided nickel, palladium or platinum.

When ethyl iodide is heated with excess of alcoholic ammonia, under pressure at 373 K ethanamine is obtained as a major product.