Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield

Chapter 18, Problem 18.59

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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 oxygens bonded to the same carbon. catalyst H+ A hemiacetal An acetal C O OR C ROH + + H2O OH OR C OR H+ ROH (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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