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Q.

Consider the following anions

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When attached to SP3 – hybridized carbon, their leaving group ability in nucleophilic substitution reaction decreases in the order : 

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a

i > ii > iii > iv

b

i > ii > iv > iii

c

iv > i > ii > iii

d

iv > iii > iii > i

answer is B.

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Detailed Solution

Good leaving group is the conjugate base of strong acid.

When attached to sp3−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 3O 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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