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we know that the phenoxide ion has more resonating structuers than the carboxylate ion, then why is phenol less acidic than carboxylic acid ?????????

we know that the phenoxide ion has more resonating structuers than the carboxylate ion, then why is phenol less acidic than carboxylic acid ?????????

Grade:12

1 Answers

Ramesh V
70 Points
11 years ago

You shld know that, resonance stabilisation  exists for both . 

                            
 for carboxylic acid -conjugate base -(2 equal resonance structures )        
and   for  phenoxide - 5 resonance structures. ( but in these 5  , 3structures lose aromaticity ,
hence contribute less)

hence ,the hybrid stability decreases as compared to  carboxylate ion.  
          basicity-    phenoxide > carboxylate
          acidity-      carboxylic acid > phenol              

The proof- carboxylic acid reacts with Na2CO3,  PHENOL DOESnt

any kind of doubts are most welcome through this portal

best of luck

--

regards

Ramesh

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