Arrange the following in increasing order of electrophilic strength :

III > I > II

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I > III > II

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I > II > III

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III > II > I

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Solution

The correct option is D I > II > III
Compound $I I I$ has total $6 π$ electrons. $4 n + 2 = 6 \Rightarrow n = 1$ . It is an aromatic carbocation, so it would not accept more electrons as it will loose its aromaticity.

Similarly carbocation $I$ has $4 π$ electrons and is not aromatic. To become aromatic it would readily accept electron thus is stronger electrophile.

Carbocation $I I$ do not have $π$ electrons so doesn't related to aromatic behavior but its a tertiary carbocation so its more stable and weaker electrophile.

The order of electrophilic strength is $I > I I > I I I$ .

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