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Question

Statement-I: Pyrrolidine (II) is more basic than pyrrole (I).
Statement-II : Protonated pyrrole has resonance stabilization of positive charge in aromatic ring.

A
Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I
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B
Statement-I is True, Statement-II is True ; Statement-II is NOT a correct explanation for Statement-I
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C
Statement-I is True, Statement-II is False
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D
Statement-I is False, Statement-II is True
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Solution

The correct option is C Statement-I is True, Statement-II is False
The difference in the structures of pyrrolidine and pryrrole results in a difference basicity of the two compounds. pyrrolidine does not have any double bonds while pyrrole has them. As a result, pyrrole is an aromatic compound which limits the availability of the lone pair of electrons on the nitrogen for bonding with electrophiles. Since the electrons are less available for bonding, they are weaker electron donators and therefore a weaker base. Pyrrolidine does not have the double bonds and is not aromatic so the lone pair of the N is more available (more easily donated) so it is a strong base.

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