question archive Ethanol CH3CH2OH is not considered an acid or base, even though there is an H+ and two lone pairs on the oxygen atom

Ethanol CH3CH2OH is not considered an acid or base, even though there is an H+ and two lone pairs on the oxygen atom

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Ethanol CH3CH2OH is not considered an acid or base, even though there is an H+ and two lone pairs on the oxygen atom. What atoms could be changed on this molecule other than the OH to create a compound that would be more acidic? (Hint: there are many correct answers)

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Molecules that are more acidic than ethanol by replacing atoms other that OH.

  1. CF3CH2OH
  2. CHF2CH2OH
  3. CH2FCH2OH
  4. CCl3CH2OH
  5. CHCl2CH2OH

Higher the stability of conjugate base higher is the acidity. the conjugate base of ethanol is the weakest because the + I effect of the ethyl group increases electron density upon oxygen atom which is already having an extra electron thus destabilizing it the most.

-I effect on the resonance hybrid group stabilizing it by withdrawing electron density due to higher electronegativity of hybridised carbon. here atoms F, Cl have high -I effect which makes these compounds are more acidic then ethanol.