Question

why pyrrole is more basic than amide​

Answer 1

Amines and Amides

Amines and AmidesAs a result, pyridine is a weaker base (larger pKb) than an alkylamine. Pyrrole is an exceedingly weak base. The pair of electrons of the nitrogen atom interacts with the four electrons of the two carbon-carbon double bonds to give an aromatic six-π-electron system similar to that of benzene.

Answer 2

Answer:

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Explanation:

Q. Why pyrrole is more basic than amide?

• The basicity of amines of different classes do not follow a simple pattern because the number of groups bonded to nitrogen affects the electron density at the nitrogen atom. And, the stability of the conjugate acid in the solvent has a major affect on basicity. Thus, the basicity of amines can be explained only for amines with similar structures at the nitrogen atoms.

• The basicity of an amine is increased by electron-donating groups and decreased by electron-withdrawing groups. Aryl amines are less basic than alkyl-substituted amines because some electron density provided by the nitrogen atom is distributed throughout the aromatic ring. Basicity is expressed using Kb values measured from the reaction of the amine with water. An alternate indicator of basicity is pKb, which is −log Kb. A strong base has a large Kb and a small pKb. The basicity of amines is also expressed by the acidity of their conjugate acids. A strong base has a weak conjugate acid, as given by a small value of Ka and a large pKa.

• The basicity of heterocyclic amines depends on the location of the electron pair of the nitrogen atom, its hybridization, and whether or not resonance stabilization is possible. In pyrrole, the electron pair is part of the aromatic system. As a result, pyrrole is a very weak base. Pyridine is a weaker base than saturated amines of similar structure because its electron pair is in an sp2-hybridized orbital, and the electron pair is more tightly held by the atom. Protonation of a similar nitrogen atom in pyrimidine is more favorable because the charge is delocalized to the second nitrogen atom.

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