Help with Keto-Enol Tautomerization - Organic Chemistry
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Which of the following results in a single ketone product following acid catalyzed hydration?
Which of the following results in a single ketone product following acid catalyzed hydration?
During acid catalyzed hydration, a hydroxy group replaces one of the bonds in the triple bond and a double bond is formed. This is called an enol. The enol naturally turns into a ketone in a process called tautomerization. The hydroxy group can attach to either carbon across the double bond, and naming is done so that substituents have the lowest numbers. Only on 5-decyne will result in a single product, as no matter which carbon the hydroxy group bonds to, it is still on carbon 5. Thus, the only final product is 5-decone.
The other answer options will still react, but will form multiple products due to lack of symmetry.
During acid catalyzed hydration, a hydroxy group replaces one of the bonds in the triple bond and a double bond is formed. This is called an enol. The enol naturally turns into a ketone in a process called tautomerization. The hydroxy group can attach to either carbon across the double bond, and naming is done so that substituents have the lowest numbers. Only on 5-decyne will result in a single product, as no matter which carbon the hydroxy group bonds to, it is still on carbon 5. Thus, the only final product is 5-decone.
The other answer options will still react, but will form multiple products due to lack of symmetry.
Compare your answer with the correct one above
What is the product of the reaction shown?
What is the product of the reaction shown?
First step: bromination across the double bond
Second step: double dehydrohalogenation and removal of terminal alkyne hydrogen
Third step: neutralization of the molecule
Fourth/fifth step: hydroboration/oxidation, followed by keto/enol tautomerization
First step: bromination across the double bond
Second step: double dehydrohalogenation and removal of terminal alkyne hydrogen
Third step: neutralization of the molecule
Fourth/fifth step: hydroboration/oxidation, followed by keto/enol tautomerization
Compare your answer with the correct one above