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Compare the basicity of the following compounds: a) Heterocycles: 1,2,3,4-Tetrahydroacridine (contains nitrogen in a six-membered heterocycle connected to a benzene ring). indole (a five-membered heterocycle with nitrogen connected to a benzene ring).
Accepted Answer
The basicity of these heterocycles is determined by the availability of the lone pair of electrons on the nitrogen atom. Here's a comparison:
1,2,3,4-Tetrahydroacridine: The nitrogen atom in tetrahydroacridine is sp3 hybridized and has a lone pair that is more readily available for protonation, making it a stronger base.
Indole: The nitrogen atom in indole is sp2 hybridized and its lone pair is delocalized into the aromatic system. This delocalization makes the lone pair less available for protonation, reducing its basicity.
Therefore, 1,2,3,4-tetrahydroacridine is a stronger base than indole.
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