why is Na/C2H5OH not preferred in the reduction of carboxylic acid to alcohols, despite being used for esters?

  • $\begingroup$ You could get deprotonation as a side reaction, because the reagent generates a strong protic base (ethoxide ion). $\endgroup$ Dec 1, 2018 at 10:04
  • $\begingroup$ Correct. You get the sodium carboxylate which does not reduce. $\endgroup$
    – Waylander
    Dec 1, 2018 at 10:19

1 Answer 1


As the comments point out: the sodium in ethanol generates sodium ethoxide, just as sodium in water generates the hydroxide. The ethoxide ion, acting as a strong base, deprotonates the acid to a salt and thwarts the reduction. Get rid of the easily removed proton by using an ester and you unleash the reduction reaction you want.


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