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Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with ...

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Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with ...

Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms a hydrochloride salt, whereas pyrrole is unreactive. Which of the following is not a valid explanation for this observed reactivity?

▸ The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.

▸ The lone pair on pyridine is not part of the aromatic system.

▸ Protonation of pyrrole leads to a nonaromatic cation, which is less stable.

▸ The lone pair on pyrrole is sp3 hybridized and is less prone to protonation.

▸ The lone pair on pyridine can be protonated without disrupting the aromatic stability.

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Organic Chemistry

Edition: 4^th

Author: Klein

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