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Problems and exercisesHeteroaromatic Compounds

1. Basicity of imidazole

Why is imidazole almost 100 times more basic than pyridine?

Imidazole (pKb = 7.0) and pyridine (pKb = 8.8), with their structures and molecular models

2. SEAr on heterocycles

Predict the result of the following reactions:

Nitration of furan with HNO₃/Ac₂O, SEAr intermediates at positions 2 and 3 of pyrrole, furan and thiophene, bromination of pyridine, nitration of 4-phenylpyridine and alkylation of 3-phenylpyrrole with propene

3. Which ring reacts?

Rank in order of decreasing reactivity towards SEAr: benzene, pyridine, pyrrole and thiophene.

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