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anmol verma Grade: 12
        

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

7 years ago

Answers : (1)

Ramesh V
70 Points
										

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

7 years ago
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