Why does the nitration of aniline give meta product?

Aniline reacts with acid to give anilinium ion which deactivates the ring towards electrophilic substitution especially at para and ortho positions. However, meta position is not deactivated. Hence more meta product is formed.

What is the reason for the formation of meta product?

Aniline on protonation gives anilinium ion which is meta directing. So considerable amount of meta product is formed.

Why nitration of aniline is not possible?

Direct nitration of aniline is not a feasible process because nitric acid oxidizes most of aniline to give tarry oxidation products along with only a small amount of nitrated products. By doing this it gets oxidized into protonated aniline which gives 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.

Why aniline is meta directing?

The NH2 group in aniline is ortho and para guiding group because due to resonance, they will release electrons to the ring and at the same time remove the electrons towards themselves due to +1 impact from the aromatic ring. The substituent is called a meta directing group if the opposite is observed.

Why aniline Cannot undergo nitration reaction with hno3?

Direct nitration of aniline is not a feasible process because nitric acid oxidises most of aniline to give tarry oxidation products along with only a small amount of nitrated products.

Why is aniline acetylated before nitration?

Acetylation is performed before nitration of aniline. Direct nitration isn’t administered because NH2 may be a highly activating group and it’ll result in the reaction between NH2 and HNO3. In the above reaction, aniline may be a moderate base as it’s an electron rich compound and acts as a good nucleophile.

Is direct nitration of aniline possible?

Answer: Direct nitration of aniline is not possible. so NO2 reacts with NH2 instead of coming to benzene ring of aniline so to make possible the reaction of nitration of aniline , acetylation of NH2 grp is done to make it less reactive for coming NO2 grp nd this acetylation called schotten baumen reaction.

Why direct nitration of aromatic amine is not recommended?

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

Is meta directing or not?

Thus, the nitro group is a meta directing group. Ortho, para directing groups are electron-donating groups; meta directing groups are electron-withdrawing groups. The halide ions, which are electron-withdrawing but ortho, para directing, are the exception.

Why nitration of aniline is carried out after acylation?

(a) Acylation activates the -NH2 group.

Why does aniline form a meta product of NO2?

Aniline react with mixture of conc.nitric acid and sulfuric acid to give m-nitroaniline . As we know nitric acid is a protonic acid and when it react with amino gruop ,it form anilinium ion (C6H5NH3+). Because of +ve charge -NH3+ group is meta directing and also a activating gruop.this why aniline form a meta product of NO2.

Does nitration of aniline take place in acidic or basic medium?

As far as i can remember, nitration takes place in acidic medium. In acidic medium, aniline converts to anilium ion (NH3+) and since it is meta director,tge meta product is major. But the difference in meta and para isomer is very little.

What happens when Aniline reacts with HNO3?

-NH2 is a strongly activating group and ortho- para directing but, when aniline reacts with HNO3 in acidic medium, firstly acid-base reaction takes place between HNO3/ H2So4 and aniline and anilinium ion is formed. Due to presence of -NH3+ group in anilinium ion (which is meta directing) Meta product is formed.

Why do we obtain picric acid After nitration of phenol?

Why is it when we do a nitration of phenol, we obtain ortho-, para-, mono-, and nitro- derivatives of phenol, but when we do a nitration followed by sulphonation, we obtain picric acid? The OH group of phenol is so activating that the nitration mixture rapidly overheats even with dilute nitric acid.