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Question

Arrange in the increasing order of nucleophilicity.

CF3CO2−, CI3CO2−, CH3CH2CO2−

A
CF3CO2>CI3CO2<CH3CH2CO2
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B
CF3CO2<CI3CO2>CH3CH2CO2
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C
CF3CO2>CI3CO2>CH3CH2CO2
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D
CF3CO2<CI3CO2<CH3CH2CO2
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Solution

The correct option is D CF3CO2<CI3CO2<CH3CH2CO2
In the polar aprotic solvent, the increasing order of nucleophilicity is CF3CO2<CI3CO2<CH3CH2CO2.
The decreasing order of electronegativity is F>I. When trifluoromethyl (or triiodomethyl) group is present, the nucleophilicity decreases due to the electron withdrawing effect of trifluoromethyl (or triiodomthyl) group. The decrease is more pronounced in trifluoroacetate ion than in triiodoacetetate ion.

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