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Resonance Effect

consider the ...

Question

consider the following species, when attached to sp $^{3}$ hybridized carbon, their leaving group ability in nucleophilic substitution reactions decreases in the order.
(I) $C F_{3} - O | | S | | O - O^{⊖}$
(II) $C_{6} H_{5} - O | | S | | O - O^{⊖}$
(III) $C_{6} H_{5} - O^{⊖}$
(IV) $C H_{3} - O | | C - O^{⊖}$

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Solution

Leaving group ability depends upon stability of anions(more resonating structure on more electronegative atom is more stable).
So, $I > I I > I V > I I I$

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