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Which of the following statements does NOT correctly describe a keto-enol tautomerism?A.The reaction results in a pi bond migration, forming a C=C double bond.B.The reaction can be acid-catalyzed by protonating an enol oxygen atom.C.The reaction involves removal of a proton from an α-carbon.D.The reaction results in an equilibrium mixture of keto and enol tautomers, which are constitutional isomers.

Question

Which of the following statements does NOT correctly describe a keto-enol tautomerism?A.The reaction results in a pi bond migration, forming a C=C double bond.B.The reaction can be acid-catalyzed by protonating an enol oxygen atom.C.The reaction involves removal of a proton from an α-carbon.D.The reaction results in an equilibrium mixture of keto and enol tautomers, which are constitutional isomers.

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Solution

The statement C does NOT correctly describe a keto-enol tautomerism. In keto-enol tautomerism, a proton is not removed from an α-carbon. Instead, a proton is transferred from an α-carbon to a carbonyl oxygen in the keto form to form the enol form.

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