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QUestion
Which of the following statements is true regarding the basicity of N-methylimidazole?
(A)
It is protonated on N-1 because the resulting cation retains aromaticity.
(B)
It is protonated on N-3 because the resulting cation retains aromaticity.
(C)
Protonation on either N atom forms a cation that retains aromaticity.
(D)
N-methylimidazole is not basic because protonation on either N atom destroys aromaticity.
(E)
N-methylimidazole is most readily protonated on a carbon atom, which forms a cation that retains aromaticity.
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