Account for the following: Although the Amino group is o and p directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-Nitroaniline?

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Solution

Aniline on nitration gives a substantial amount of m-Nitroaniline:
The Nitration process usually undergoes in the presence of an acidic medium i.e the mixture of $Con {HNO}_{3}$ and $Con H_{2} {SO}_{4}$ , which results in the protonation of the Anilinium ion, and Nitroaniline is formed.
The formed Anilium ion basically acts as a deactivating group and directs the nitro $(- {NO}_{2})$ group to the meta position by forming a meta isomer of Nitroaniline.
Also, the nitro group which is an electron-withdrawing group does not undergo Friedel craft reaction on ortho and para position as it deactivates the benzene ring mainly at the respective ortho and para position for electrophilic substitution reaction.
Hence, aniline on nitration gives a substantial amount of m-Nitroaniline.

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Account for the following:

(i) pK_bof aniline is more than that of methylamine.

(ii) Ethylamine is soluble in water whereas aniline is not.

(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.

(iv) Although amino group is o, p− directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.

(v) Aniline does not undergo Friedel-Crafts reaction.

(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.

(vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.

Account for the following

(i) $p K_{b}$ of aniline is more than that of methyl amine.

(ii) Ethylamine is soluble in water whereas aniline is not

(iii) Methyl amine in water reacts with ferric chloride to precipitate hydrated ferric oxide

(iv) Although amino group is o- and p- directing in aromatic electrophilic substitution, aniline on nitration gives a substantial amount of m-nitroaniline

(v) Aniline does not undergo Friedel Crafts reaction

(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines

(vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines

Q. Although the amino group is 0- and p-directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of nitroaniline.
If this is true enter 1 if false enter 0.

Q. Amino group is ortho, para-directing for aromatic electrophilic substitution. On nitration of aniline good amount of m-nitroaniline is obtained. This is due to:

Q. Amino group is o, p-directing for electrophilic substitution reaction. But, on nitration the major product is m - nitroaniline because:

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