Ionic species are stabilised by the dispersal of charge Which of the following carboxylate ion is the most stable :

C H_{3} - O | | C - O^{⊝}

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C l - C H_{2} - O | | C - O^{⊝}

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F - C H_{2} - O | | C - O^{⊝}

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_{F}^{F} > C H - O | | C - O^{⊝}

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Solution

The correct option is D $_{F}^{F} > C H - O | | C - O^{⊝}$
Ionic species are stabilized by the dispersal of charge.

The carboxylate ion D $(F_{2} C H C O O^{-})$ is the most stable.

The negative charge on O is dispersed through resonance in the carboxylate group.

The negative charge is further dispersed due to negative inductive effect (-I effect) of two F atoms present on alpha carbon atoms.

The decreasing order of -I effect is $F - C H_{2} - > C l - C H_{2} > H_{3} C -$ .

In fact, methyl group +I effect and destabilizes the carboxylate ion.

Hence the correct option is D.

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C H_{2} = O H | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O H | C = C H - O | | C - C H_{3}

I

I I

I I I

C H_{2} = O H | C - C H_{2} (I) - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} (I I) - O | | C - C H_{3}

⇌ C H_{3} - O H | C = C H (I I I) - O | | C - C H_{3}

C H_{3} - C H = C H - C H_{2} - O | | C - C H_{3} \to C H_{3} - C H = C H - C H_{2} - O | | C - O H

C H_{3} - O | | C - C H_{2} - O | | C - O - C_{2} H_{3}

C H_{3} - O H | C = C H - O | | C - O - C_{2} H_{5}

B r {C H}_{2} - {C H}_{2} - C H = O

{C H}_{3} - {C H}_{2} - C | B r = O

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