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Question
CH3CO2H or CH2FCO2H
Solution
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It is difficult for the proton to escape because the +I effect of −CH3 group increases the electron density in the O–H bond. |
The release of the proton is easy because the −I effect of −F reduces the electron density in the O–H bond. |
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The +I effect due to the concentration of negative charge destabilises the carboxylate ion. |
The spreading of the negative charge causes the –I effect to stabilize the carboxylate ion. |
Hence, due to lower electron density in the O–H bond and higher stability of FCH2COO– ion, FCH2COOH is a stronger acid than CH3COOH.
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\[\begin{array}{cc}
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