Rank the following in the decreasing order of their rates with methoxide ion $(C H_{3} O^{-})$ in a nucleophilic aromatic substitution.

3 > 4 > 1 > 2

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2 > 1 > 4 > 3

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3 > 4 > 2 > 1

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4 > 3 > 2 > 1

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Solution

The correct option is A $3 > 4 > 1 > 2$
$N O_{2}$ shows -R as well as -I effect but former predominates when the substitution occurs at ortho or para position to $N O_{2}$ group.
[3] will be the most reactive as both nitrogen are at ortho and para to leaving group.
[2] will be the least reactive as only -I effect is working.
Hence the order is: $3 > 4 > 1 > 2$

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Rank the following in the decreasing order of their rates with methoxide ion (CH3O−) in a nucleophilic aromatic substitution.

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