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Show the mechanism for the dinitration of 2-benzylpyridine. Use resonance structures to explain the 2,4-substitution pattern...

Show the mechanism for the dinitration of 2-benzylpyridine. Use resonance structures to explain the 2,4-substitution pattern on the phenyl ring and why nitration the pyridine ring is unfavored.
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Answer #1

Nitration takes place on benzene ring rather than pyridine ring because pyridine ring is electron poor (when compared to benzene) due to the presence of the nitrogen, which pulls electrons towards itself via the inductive effect, and thus it doesn't undergo aromatic electrophilic substitution easily.

Now, in benzene ring nitration takes place at ortho and para position because -CH2 group attached to the benzene ring has ortho, para directing effect due to the higher electron density on these positions in its resonating structures.

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