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Monday, February 3, 2020

Alcohols and Phenols both are acidic but phenols are more acidic. Why?

Alcohols and phenols both are acidic in nature because they Liberate H2 with active metals. But alcohols are weaker acids than phenols because,  
(i) Alcohols fail to turn blue litmus red:
(ii) Alcohols fail to neutralize alkalies whereas phenols do so:
(1) Both phenol and phenoxide ions exhibit resonance, whereas alcohols and alkoxide ion do not.
(2) Due to resonance, positive charge 's developed over "O" of phenol this weakens O-H bond and facilitates release of a proton. On the other hand due to electron donating nature of alkyl group -O-H bond is strengthened. Therefore it hinders the release of proton.      
(3) The phenoxide ion is more stable than phenol, due to greater dispersal of negative charge, therefore. Equilibrium get shifted to forward direction. whereas alkoxide ion is less stable than alcohols due to intensification of negative charge, so equilibrium get shifted towards backward direction. Hence phenols are more acidic than alcohols. 

Related Questions:

Phenoxide ion is more stable than an alkaoxide. why?

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