Question

Tony was working in a laboratory. He needed to work up a reaction that used concnetrated sulfuric acid. Tony's boss told him to use diethyl ether but he mistakenly used ethyl acetate. Tony mixed the ethyl acetate and the acid/aqueous layer and was waiting for the two to separate but they never did. What happened to the ethyl acetate under the strongly acidic conditions? Why would diethyl ether have been a better solvent?

Answer 1

Under strongly acidic conditions, ethyl acetate will hydrolyze to form ethanol and acetic acid. both the products are soluble in water. Thus we will not observe a separate layer corresponding to the organic layer in the separating funnel.

C2H5-COO-CH3 will give CH3COOH + C2H5OH (under acidic conditions)

At the same time, ether reaction with acid is very slow (it will take place only in the presence of strong nucleophile). Thus it will give 2 separate layers and one can easily separate them.