Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds that have one alcohol-like oxygen and one ether-like oxygen bonded to the same carbon. Further reaction of a hemiacetal with alcohol then yields an acetal, a compound that has two ether-like oxygen?s bonded to the same carbon.

(a) Show the structures of the hemiacetal and acetal you would obtain by reaction of Cyclohexanone with ethanol.

(b) Propose a mechanism for the conversion of a hemiacetal into an acetal.

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OR OR н* catalyst ROH ROн H20 н* OR но, A hemiacetal An acetal