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Resonance Effect

The correct o...

Question

The correct order of decreasing basic strength is:

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 V > I I I

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I I > I I I > I V > I

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Solution

The correct option is A $I I > I > I V > I I I$
Two of the factors which influence the strength of a base are:
-The ease with which the lone pair picks up a hydrogen ion.
-The stability of the ions being formed.
In benzyl amine $C_{6} H_{5} - C H_{2} N H_{2}$ , the lone pair of nitrogen is not in conjugated system, therefore, its easy availability to donate makes it a stronger base. In aniline $C_{6} H_{5} - N H_{2}$ , lone pair of electrons is in conjugated system with benzene ring, thus is less available. In p-nitroaniline $N H_{2} - C_{6} H_{5} - N O_{2}$ the nitro group exhibits $- M$ effect which withdraw the electrons and make it least basic. In acetanilide $C_{6} H_{5} - N H C O C H_{3}$ , strong electron withdrawing effect of the carbonyl oxygen on the amide makes it less basic. Therefore, the order of basicity is $I I > I > I V > I I I$ .

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