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Which of the following represents the correct order of basic strength?

1. o-Methylaniline > Aniline
2. Pyridine > Aniline
3. Urea > Guanidine
4. Phenol > Benzyl alcohol

Correct answer: Pyridine > Aniline

Solution

Pyridine is more basic than aniline because the lone pair on nitrogen in aniline is delocalized into the benzene ring (resonance), reducing its availability for protonation. o-Methylaniline is actually less basic than aniline due to steric hindrance (ortho effect) despite the +I effect of methyl.

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