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Question
Which acid of the pair shown here would you expect to be stronger?
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Solution
|
−CF3 has a strong −I effect, stabilising the carboxylate ion by dispersing the negative charge. |
−CF3 has weak +I effect, it destabilises the carboxylate ion by condensing the negative charge. |
Therefore, F3C–C6H4–COO– (p) ion is more stable than CH3–C6H4COO– (p) ion because of F3C–C6H4–COO– (p) ion.
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\[\begin{array}{cc}
\ce{O}\phantom{...............................................}\\
||\phantom{...............................................}\\
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