Give a plausible explanation for why are amines less acidic than alcohols of comparable molecular masses?
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(i) The loss of a proton from an amine gives an imide ion, while the loss of a proton from alcohol gives an alkoxide ion as shown below:
R – O – H → R – O⊖ + H⊕
Since O is more electronegative than N, therefore, (RO⊖) can accomodate the negative charge more easily than R⊖NH can accomodate the negative charge.
In other words, RO⊖ is more stable than R⊖NH. Thus, alcohols are more acidic than amines. Conversely, amines are less acidic than alcohols.
(ii) 1º amines form stronger intermolecular H-bonding between N atom of one and H atom of another molecule.
(iii) Aliphatic amines are stronger bases due to the +I effect of the alkyl group, leading to high electron density on the N atom.