More stable conjugate base of a phenol?

[Addallat]

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Which winds up with a more stable conjugate base of a phenol:

a phenol with a ortho substituted electron withdrawing group

or


a phenol with a para substituted electron withdrawing group?


Please explain your logic

 

[Addallat]

answering my own question

it would depend on what the withdrawing group is

logic is resonance before induction


e.g

CBr3 ortho phenol makes for the more acidic phenol than CBr3 para phenol due to induction

NO2 para phenol makes for the more acidic phenol over NO2 ortho phenol due to resonance


Please confirm or debate my logic thanks

 

[gwjib04]

Makes perfect sense to me

Stronger acids are better bases therefore they stabilize negative charges better. EWG's decrease the electron density of the aromatic ring and spead it out further which is more favorable.