Organic Chemistry

Abhijeet Narang's Avatar
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3 Nov 2011 19:06:29 IST
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acidic character
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which is more acidic and why?phenol or carboxylic acid

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Cool goIITian

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3 Nov 2011 19:57:02 IST
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carboxylic acid is more acidic because if we analyze their conjugate bases- in carboxlic acid the -ve charge resides only on O(electronegative element) but in case of phenol the -ve charge resides on C.Hence the resonating structures of phenol are less contributing than the resonating structures of carboxylic acid.

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4 Nov 2011 08:21:11 IST
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Carboxylic acids are more acidic.Not only it can turn litmus paper but it can also react with carbonates and bicarbonates

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5 Nov 2011 14:09:17 IST
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Carboxylic acids are more acidic than Phenol...this is attributed to the greater stability of the carboylate ion as compared to the phenoxide ion....(acidity can be judged by the stability of conjugate base formed after removing H+)...In carboylate ion the -ve charge is dispersed on 2 more electro-ve Oxygen atoms as compared to phenoxide in which -ve charge is distributed on 1 electro-ve O and lesser electro-ve carbons...
Madhusudan Chavan's Avatar

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5 Nov 2011 17:06:45 IST
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Carboxylate ion is more stable than the phenoxide ion as the negative charge is evenly spread on the carboxylate ion,

In case of phenoxide ion, three contributing structures have a negative charge on the less electronegative carbon atom. Therefore their contribution towards the resonance stabilization of the phenoxide ion is very small.

In the carboxylate ion the negative charge is delocalized on the two oxygen atoms, while in phenoxide ion the negative charge remains localized on the oxygen atom only (considering the remaining two contributing structures of the phenoxide ion). Thus carboxylate ion is much more resonance stabilized than the phenoxide ion.Hence release of proton from carboxylic acid is much more easier than phenol.

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5 Nov 2011 17:29:41 IST
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Abhijeet Narang's Avatar

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5 Nov 2011 19:28:23 IST
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thnx sir

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