Dolbier HW Solutions 525 - 619 AMINES 22.26(a An alkyl...

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22.26 ( a ) An alkyl substituent on nitrogen is electron-releasing and base-strengthening; thus methyl- amine is a stronger base than ammonia. An aryl substituent is electron-withdrawing and base- weakening, and so aniline is a weaker base than ammonia. ( b ) An acetyl group is an electron-withdrawing and base-weakening substituent, especially when bonded directly to nitrogen. Amides are weaker bases than amines, and thus acetanilide is a weaker base than aniline. Alkyl groups are electron-releasing; N -methylaniline is a slightly stronger base than aniline. ( c ) Chlorine substituents are slightly electron-withdrawing, and methyl groups are slightly electron-releasing. 2,4-Dimethylaniline is therefore a stronger base than 2,4-dichloroaniline. Nitro groups are strongly electron-withdrawing, their base-weakening effect being especially pronounced when a nitro group is ortho or para to an amino group because the two groups are then directly conjugated. ( d ) Nitro groups are more electron-withdrawing than chlorine, and the base-weakening effect of
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