India Site

Give a plausible explanation for each of the following:
(i) Why are alcohols more acidic than amines of comparable molecular masses?
(ii) Why do tertiary amines have lower boiling points than primary amines?

(i) protonation of amines gives amide ion.

Similarly, alcohol gives away a proton which results in alkoxide ions.

In an amide ion, the negative charge is on the N-atom, whereas in an alkoxide ion, the negative charge is on the O-atom. Due to the fact that O is more electronegative than N, it may easily hold a negative charge. As a result, the alkoxide ion has higher stability than the amide ion. Therefore, alcohols are more acidic than amines of comparable molecular masses.

(ii) In a tertiary amine molecule, there are no hydrogen atoms, whereas primary amines have two hydrogen atoms. Because of the existence of H atoms, primary amines undergo significant intermolecular H – bonding.

As a result, more energy would be needed to separate the molecules of primary amines. As a result, the boiling temperatures of tertiary amines are lower than those of primary amines.