In each of the following pair of compounds, which is more basic in aqueous solution? Give an explaination for your choice:

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Solution

(i) Presence of an electron-withdrawing group decreases the lone pair availability on Nitrogen. Hence, $C H_{3} N H_{2}$ is more basic than $C F_{3} N H_{2}$ .
(ii) $2^{n d}$ compound has more nitrogen atoms and hence more lone pair availability. Therefore, (Refer to Image) is more basic than $C H_{3} C O N H_{2}$ .
(iii) In $C H_{3} C N$ , there is a triple bond between $C$ and $N$ ,. Its lone pair is less available. On the other hand, lone pair availability is more in $P h N H_{2}$ . Therefore, $P h N H_{2}$ is more basic than $C H_{3} C N$ .

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