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  • Comparing the basicity of aniline and ortho anisidine
    p-anisidine should be more basic than aniline But the main problem is comparing the basicity of aniline and o-anisidine and comparing them with p-anisidine I doubt the presence of ortho effect in ortho isomer after seeing the ball and stick model which makes the interaction of lone pair of nitrogen with hydrogen atoms of $\ce{-OCH3}$ improbable
  • How to compare acidity in the following aniline derivatives?
    According to source the pKa values (of the conjugate acid) are: compound °C pKa Aniline 25 4 87 2-Methoxyaniline 25 4 53 3-Methoxyaniline 25 4 20 4-Methoxyaniline 25 5 36
  • Is nitrogen of aniline sp² or sp³ hybridized? [duplicate]
    The pKa for the pyridine systems is 5 2, for aniline it is 4 6 So pyridine is a stronger base We can link this to the availability of the lone pair in pyridine, as it is not delocalized ( perpendicular to the aromatic $\pi$ system While in aniline the nitrogen lone pair can be delocalised using resonance with the adjacent $\pi$ system
  • organic chemistry - Why dont phenol behave like aniline in . . .
    I mean in the solution of nitration (conc HNO3 + conc H2SO4), H3O+ is present, which has a pKa of 1 7 When pKa = 1 7 compared to pKa of phenol = 10 0, the equilibrium favors the phenol being protonated by around 10^8 times, which I think can be said irreversible too This causes me to wonder why phenol does not behave as aniline in this case
  • Acidic Strength comparison - Chemistry Stack Exchange
    $\begingroup$ The pKa of aniline is ~30 that of water is 14 pKa is logarhythmic scale so the aniline proton is approx 10^16 less acidic than water $\endgroup$ – Waylander Commented Sep 2, 2023 at 21:05
  • organic chemistry - Why does p-aminophenol oxidize in acid solution . . .
    The pKa might be low enough, that the deprotonation can even happen in acidic solution Alternatively, the reaction might also proceed via a concerted mechanism, where both a proton and an electron are transfered at the same time In that case, pKa values don't apply anymore
  • Why is phenol more acidic than aniline? - Chemistry Stack Exchange
    Electronegativity is usually the main factor The pKa difference between alcohols and amines is ~20 which is quite large; a difference in the extent of resonance delocalisation isn’t likely to affect pKas by that much (Compare for example methane (pKa 50) vs toluene (41)
  • Can aniline autodeprotonate? - Chemistry Stack Exchange
    However, the $\mathrm pK_\mathrm a$ of aniline is 27, which means, that it is, if at all, a very very poor acid, making it in my eyes impossible to deprotonate Maybe it could be possible with n-BuLi, but that was not part of the reaction The main topic was a nucleophilic aromatic substitution to 1-bromo-4-nitrobenzene, with aniline


















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