Engineering
Chemistry
Inductive Effect
Basic Concepts of GOC
Acidic and Basic Oxides
Question

Give a plausible explanation for why are amines less acidic than alcohols of comparable molecular masses?

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Solution
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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 Amine -NH2R-NH Imide ion +H

R – O – H → R – O + H

Since O is more electronegative than N, therefore, (RO) can accomodate the negative charge more easily than RNH can accomodate the negative charge.

In other words, RO is more stable than RNH. 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.