Why Na/C2H5OH not preferred in the reduction of carboxylic acid, despite being used for the reduction of esters

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




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.


 7