Question

I wanted to compare the acidic strength of aniline and water.

Water on losing hydrogen gives OH−
and aniline on releasing H gives Ph−NH−
and this -ve charge goes into resonance so the -ve charge is distributed, then which one is has more acidic strength??

If it is aniline then it should react with NaOH
, since water, which is comparatively weaker acid is formed as a product, then why does it not do so

Please tell me if i am wrong somewhere in my logic and which one is more acidic.

Answer 1

Aniline is a weaker acid than water because aniline's conjugate base is less stable due to the electron-donating effect of the benzene ring, despite the resonance stabilization. Aniline does not react with NaOH in water due to the leveling effect.

Step-by-step explanation:

To compare the acidic strength of aniline and water, one must consider the stability of the conjugate base formed after donation of a hydrogen ion (proton). When water loses a hydrogen ion, it forms hydroxide (OH−), while aniline forms phenylamine (PhNH−), which can resonate to distribute the negative charge.

Resonance stabilization typically increases the stability of a base, suggesting that aniline could be more acidic than water. However, the presence of a benzene ring and its electron-donating effect in aniline reduces the tendency to release a proton, making aniline a weaker acid compared to water.