Arrange the following compounds in decreasing order of their reactivity with sodium methoxide in methanol at $50^{\circ}$ C.

I I > I I I > I V > I

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I I \approx I V > I I I > I

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I I \approx I I I > I > I V

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I I \approx I V \approx I I I > I

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Solution

The correct option is B $I I \approx I V > I I I > I$
The reaction is an example of nucleophilic aromnatic substitution that involves the formation of carbanion as an intermediate. The carbonation from O-and p-chloronitrobenzenes are more stable than that from the m-isomer that, in turn, is more stable than that obtained from chlorobenzene, and is devoid of electron-withdrawing $- N O_{2}$ group.

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