Question: Amides are weaker bases than corresponding amines. For example, most water-insoluble amines (RNH2) will dissolve in dilute aqueous acids (aqueous HCl, H2SO4, etc.) by forming

Amides are weaker bases than corresponding amines. For example, most water-insoluble amines (RNH2) will dissolve in dilute aqueous acids (aqueous HCl, H2SO4, etc.) by forming water-soluble alkylaminium salts (RNH3+X-). Corresponding amides (RCONH2) do not dissolve in dilute aqueous acids, however. Propose an explanation for the much lower basicity of amides when compared to amines.

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