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Chemistry > Organic Chemistry > Amines

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Amines have a lone pair of electrons on nitrogen atom due to which they behave as Lewis base. Greater the value of Kb_b or smaller the value of pKb_b, stronger is the base. Amines are more basic than alcohols, ethers, esters, etc. The basic character of aliphatic amines should increase with the increase of alkyl substitution. But it does not occur in a regular manner as a secondary aliphatic amine is unexpectedly more basic than a tertiary amine in aqueous solutions. Aromatic amines are weaker bases than ammonia and aliphatic amines. Electron releasing groups such as –CH₃, –OCH₃, –NH₂ etc., increase the basicity while electron-withdrawing substituents such as –NO₂, –CN, halogens etc., decrease the basicity of amines.

(a) Arrange the following in the increasing order of their basic character. Give reason:

Three anilines: aniline, 2,4-dinitroaniline, 4-methylaniline

(b) Why is pKb_b of aniline more than that of methylamine?

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