MCQ
Consider the following anions. 

When attached to $sp^3$  -hybridized carbon, their leaving group ability in  nucleophilic substitution reaction decreases in the order

  • A
    $I > II > III > IV$
  • $I > II > IV > III$
  • C
    $IV > I > II > III$
  • D
    $IV > III > II > I$

Answer

Correct option: B.
$I > II > IV > III$
b
When attached to $sp ^3$-hybridized carbon, their leaving group ability in nucleophilic substitution reactions decreases in the order $I \,>\,II \,>\, IV \,>\, III$

$I$ is best leaving group due to electron withdrawing ($-I$) effect of trifluoromethyl group and delocalization of negative charge over $3 O$ atoms.

$III$ is worst leaving group because negative charge is delocalized over $C$ atoms.

The stabilization effect of resonance for the anion in which negative charge is delocalized over $O$ atoms is more pronounced over the delocalization in which the negative charge is delocalized over $C$ atoms.

$II$ is better leaving group than $IV$ because in $II$, the extent of delocalisation of negative charge is much more than the extent of delocalization in $IV$ .

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