Is 1.5M NaOH a strong enough base to deprotonate benzyl alcohol? Is 1.5M NaOH a strong enough base to deprotonate benzyl alcohol? I realize that NaOH generally does not deprotonate benzyl alcohol, but we performed an extraction in a Fischer esterification lab with benzyl alcohol an acetic acid to synthesize benzyl acetate. Acetic acid was added in excess, and the final ester product was purified with extraction techniques. I know that addition of NaOH removes acetic acid from the organic, diethyl ether layer, but would 1.5M NaOH also remove any remaining benzyl alcohol?
Only a very small fraction of the benzyl alcohol ($\mathrm{p}K_\mathrm{a} = 15.4$) would be removed by sodium hydroxide. Acetic acid is about 10 orders of magnitude more acidic than benzyl alcohol with a $\mathrm{p}K_\mathrm{a}$ of $4.8$, so it is completely deprotinated to form sodium acetate and water.  

For the purposes of your experiment you can assume that there is effectively no reaction between benzyl alcohol and sodium hydroxide.