Rank the following amine derivatives from highest acidity (lowest pKa value) to lowest acidity (highest pKa value). Highest acidity
anilinium ion
aniline
ammonium ion
secondary amine
amide
Lowest acidity

anilinium ion > ammonium ion > amide > aniline > secondary amine

Explanation:

Acidity of amine derivatives can derived from their pKa values.

The rule of thumb for acidity with relation to pKa values is that:

As the pKa decreases the acid strength increases and the conjugate base decreases. Similarly, as the pKa increases, the acid strength decreases and the conjugate base increase.

Hence the stronger the acid , the  lower pKa value  and the weaker the acid , the stronger the pKa value.

So the pKa value for anilinium ion = 4.6

ammonium ion = 9.4

Amide = 15

Similarly, for aniline and secondary amine, in order to determine the derivative with the higher acidity, we will consider the electron withdrawing substituent group.

The more difficult the electron are being withdraw from the electron withdrawing substituent , the more acidic the compound.

In aniline , the stabilized benzene ring attached to NH₂ makes it a less electron withdrawing group compared to the straight chains structure found in secondary amine where electron are easily withdraw by nucleophilic substitution reactions.

Thus, from highest acidity (lowest pKa value) to lowest acidity (highest pKa value).

the amine derivatives ranking is as follows:

anilinium ion > ammonium ion > amide > aniline > secondary amine