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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 ?????????

6 years ago


Answers : (1)


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




6 years ago

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