Can we carry out direct nitration of aniline?

Direct nitration of aniline is not carried out because by doing this it gets oxidised into protonated aniline which give 47\% m-nitroaniline .

Why one Cannot do the direct nitration of aniline in order to get p-nitroaniline?

Well in aniline the NH² group directs the incoming electrophile to ortho and para position. So upon direct nitration on aniline gives usually a mixture of o-nitroaniline and p-nitroaniline. In order to avoid the formation of o-nitroaniline, you have to protect the NH² group of aniline by means of acetamide.

What is direct nitration of aniline?

Direct nitration of aniline with nitric acid gives a complex mixture of mono, di- and tri- nitro compounds and oxidation products. If −NH2 group is protected by acetylation and then nitrating mixture, p-isomer is the main product.

What happens when aniline undergo nitration?

As a result, when the nitration of aniline is carried out, it not only gives nitration products but also some oxidation products. However, under controlled conditions, if the nitration of aniline is carried out, then the major products are p-nitroaniline and m-nitroaniline. Here the major product is p-Nitroaniline.

Why is meta nitroaniline obtained as major product on direct nitration of aniline?

In aniline the NH2 group is electron donating but itself acts as a lewis base and hence H+ or NO2+ first attacks the NH2 and makes the ring electron deficient . Therefore the nitration product is major in meta isomer.

Which nitric acid directly converts aniline into nitrobenzene?

aniline can be treated with a cold dilute acidic solution sodium nitrite in the temperature range of (0 – 5) 0C to form diazo compound. Then diazonium chloride is then hydrolysed in presence of hypophosphorous acid and water to form benzene.

Why aniline is meta directing in nitration?

What is direct nitration?

The direct nitration of aniline with nitric acid and sulfuric acid, according to one source, results in a 50/50 mixture of para- and meta-nitroaniline isomers. In the Wolffenstein–Böters reaction, benzene reacts with nitric acid and mercury(II) nitrate to give picric acid.

Why does nitration of aniline gives meta product?

The anilinium group, no longer possessing a free electron pair (tied up with H^+), deactivates the aromatic ring toward electrophilic substitution,also anilinium ion which is meta directive. Hence nitration of aniline gives meta derivative along with ortho and para.

Why is acetylation of NH2 group done in aniline before preparing its ortho and para compound?

Aniline has a group bonded on aromatic ring. Here the group has a lone pair which can show the resonance with aromatic ring. Also it can be given to electron deficient molecule that makes aniline basic in nature. Hence acetylation of group is done in aniline before preparing its ortho and para compounds.

What are the uses of aniline?

Aniline products are used to manufacture a variety of end-products, ranging from polyurethane foam to Kevlar™ aramid fiber to pharmaceuticals. Aniline is primarily used in the production of methylene diphenyl isocyanate (MDI) to create rigid polyurethane foams as insulators for refrigerators, freezers, and buildings.

Which is more acidic aniline or phenol?

In acidic medium phenol will undergo electrophilic substitution much faster than aniline. Both aniline and phenol undergo electrophilic substitution more easily than benzene in neutral conditions because of the +M effect of the NH2 and OH groups that activate the benzene ring at the ortho and para positions.

What is the conjugate acid of aniline?

Aniline is a resonance hybrid of five structures whereas its protonated form (conjugate acid) anilinium ion is a resonance hybrid of only two structures. The ammonium cation (protonated form) of aliphatic amine is solvation-stabilised by H2O molecules via Hydrogen-bonding.

Is aniline polar or nonpolar?

Answer = aniline ( C6H5NH2 ) is Polar. What is polar and non-polar? Polar. “In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole or multipole moment. Polar molecules must contain polar bonds due to a difference in electronegativity between the bonded atoms.