Question

pyrrole and phenol are both acidic in character justify with their structure.​

Answer 1

Answer:

The reason for the acidic character of pyrrole :

• the electron pair in the pyrrole is delocalization from nitrogen makes it positively charged and increases the possibility of proton abstraction giving pyrryl anion.
• Furthermore, the pyrryl anion is stabilized by delocalization of the negative charge over the ring.

The reason for the basic character of pyrrole:

• the lone pair of electrons in the pyrrole on nitrogen is involved in the formation of the delocalized π molecular orbital and is not available for the formation of a new bond with proton.
• Furthermore, if a proton is added to the nitrogen atom by the reaction with an acid, the resulting structure ceases to be aromatic and the resonance energy is lost.
• This makes the pyrrole cation very unstable in comparison to the free pyrrole and indicates why pyrrole is a weak base.
• Also, the pyrrole cation behaves as a typical conjugated diene and undergoes polymerization readily.

Answer 2

Acidic Character of Pyrrole:

• The electron pair in pyrrole delocalizes from nitrogen, making it positively charged
• This raises the probability of proton absorption to produce pyrryl anion,
• Additionally, the delocalization of the negative charge over the ring stabilizes the pyrryl anion.

Acidic Character of Phenol:

• The sp2 hybridized carbon atom of the benzene ring, which is directly connected to the hydroxyl group in a phenol molecule, functions as an electron-withdrawing group.
• The oxygen atom's electron density falls because this carbon atom has a higher electronegativity than the hydroxyl group it is linked to.
• Compared to phenols, the phenol oxide ion is more stable because in phenols, charge separation occurs during resonance.

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