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Although phenoxide ion has more number o...

Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Why?

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Inspite of the many resonating strụctures shown by phenoxiderion thạn the following two resonating structures shown by carboxylate.ioń, there is more dispersed of the negative charge (on two oxygen atoms).in carboxylate anion rather than on one oxygen.in phenoxide ion. Hence the corresponding acid `R-COOH` is a stronger acid than phenol `C_6 H_5 OH` figure
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Paragraph Carboxylic acids are distinctly acidic because they ionize in water to give hydronium ions: RCOOH+H_(2)O hArr RCOO^(-) +H_(3)O^(+) The acidic strength depends upon the extent of ionizations of the acid and the stability of the anion formed. The acidic strength can also be expressed in terms of dissociation constant K_(a) or pK_(a) which are related as pK_(a)= -log K_(a) . Most unsubstituted carboxylic acids have K_(a) values in the range of 10^(-4) to 10^(-5) (pK_(a) =4-5) . The substitutents have marked effect on the acidic strength of carboxylic acids. Any group that stabilizes the carboxylate ion more than the carboxylic acid group will increase the acidic strength, and the group which destabilizes the carboxylate group more than the carboxylic acid group will decrease the acidic strength. In a similar manner, the electron-releasing groups makes benzoic acid weaker, while the electron-withdrawing groups make benzoic acid stronger. The ortho isomer of every substituted benzoic acid (whether electron releasing or electron withdrawing) is the strongest among the three isomers due to ortho effect. Which of the following is the weakest acid?

V PUBLICATION-ALDEHYDES, KETONES AND CARBOXYLIC ACIDS-QUESTION BANK
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  10. How is acetone obtained from 2 - bromopropane?

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