Which of the following compounds ranks strictly as the strongest overall base when dissolved in an a β Amines Chemistry Question
Question
Which of the following compounds ranks strictly as the strongest overall base when dissolved in an aqueous medium?
Answer: A
π‘ Solution & Explanation
Acetanilide, Aniline, and p-Nitroaniline all feature a nitrogen atom whose lone pair is heavily depleted by resonance (into the carbonyl or the ring). Benzylamine, however, possesses an $sp^3$ hybridized methylene group ($-CH_2-$) that insulates the amine from the aromatic ring, blocking resonance. It behaves as a standard aliphatic amine, making it the strongest base.
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