(I) Ref. images
(II) $C H_{3} - C H_{2} - N H_{2}$
(III) $(C H_{3})_{2}$
(IV) $C H_{3} - O | | C - N H_{2}$
What is the correct order of basicity among the following compounds ?

I I > I > I I I > I V

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I > I I > I I I > I V

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I I I > I > I I > I V

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I > I I I > I I > I V

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Solution

The correct option is A $I > I I I > I I > I V$
$C H_{3} - N H | | C - N H_{2} + H^{+} ⟶ C H_{3} - N H_{2} + | C - N H_{2} \leftrightarrow C H_{3} - + N H_{2} | | C - N H_{2} \leftrightarrow C H_{3} - N H_{2} | C = + N H_{2}$
The conjugate acid formed by addition of a proton to I is stabilised by two equivalent resonance structures and hence, compound I is the most basic .Further $2^{0}$ amines (III) are more basic.than $I^{0}$ amines (II) while amides (IV) are least basic due to delocalisation of lone pair of electrons of $N$ over the $C O$ group.
Thus , the order is : $I > I I I > I I > I V$ .

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