Alcohols as Acids

• Alcohols have acidities similar to that of water.
• Sterically hindered alcohols are less acidic, causing their conjugate bases to be highly basic.
  • With an unhindered alcohol, solvent molecules can easily surround, solvate and hence stabilize the alkoxide anion formed by the loss of alcohol proton to a base. Hence the acidity of unhindered alcohols increases as in this case the formation of conjugate base is easier.
  • With a hindered alcohol, the solvation of the alkoxide is hindered and consequently the hindered alcohol is a weaker acid. Also, the alkyl groups of a hindered alcohol increase the $e^{-}$-density making the formation of an alkoxide anion harder.
• (Acidic Strength) Alcohols >> (Terminal Alkynes, Hydrogen, Ammonia or Alkanes.)
• Conjugate bases of acids with higher $p{K}_a$ values than an alcohol can deprotonate that alcohol.