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Account for : (i) Amino group is anili...

Account for :
(i) Amino group is aniline is o- and p- directing in aromatic electrophilic substitution reactions. Aniline on nitration gives a substantial amount of m - nitroaniline.
(ii) Aniline does not go Friedel Crafts reaction.

Text Solution

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(i) It is because aniline is protonated to form anilinium cation, in which` NH_(3)` group is meta - directing.
(ii) It is because aniline is basic, can form adduct with `AICI_(3)`, electrophile cannot be generated.
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Account for the following: (i) pK_(b) of 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– and 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.

Can the amino group, in the aniline molecule, become meta-directing in an electrophilic substitution reaction ?