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In Section 19-10B, we saw that pyridine undergoes

Chapter 13, Problem 56SP

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QUESTION:

In Section 19-10B, we saw that pyridine undergoes electrophilic aromatic substitution reluctantly, requiring strong conditions and giving disappointing yields. In contrast, pyridine N-oxide

undergoes EAS under moderate conditions, giving good yields of substitution on C2 and C4. Explain this surprising difference.

             

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QUESTION:

In Section 19-10B, we saw that pyridine undergoes electrophilic aromatic substitution reluctantly, requiring strong conditions and giving disappointing yields. In contrast, pyridine N-oxide

undergoes EAS under moderate conditions, giving good yields of substitution on C2 and C4. Explain this surprising difference.

             

ANSWER:

Solution 56SP

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