O A successful Claisen condensation requires an ester starting material with at least one alpha hydrogen. O The keto tautomer is usually more stable than the enol tautomer. O In a Claisen condensation, you want to match the alkoxide base with the -OR of the ester in order to avoid unwanted transesterification. O An alpha hydrogen on an ester is less acidic than an alpha hydrogen on an aldehyde. O The base-promoted halogenation of a ketone replaces all of the alpha-hydrogen atoms.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 35CTQ
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Which of the following statements is FALSE?
O A successful Claisen condensation requires an ester starting material with at least
one alpha hydrogen.
O The keto tautomer is usually more stable than the enol tautomer.
O In a Claisen condensation, you want to match the alkoxide base with the -OR of
the ester in order to avoid unwanted transesterification.
O An alpha hydrogen on an ester is less acidic than an alpha hydrogen on an
aldehyde.
O The base-promoted halogenation of a ketone replaces all of the alpha-hydrogen
atoms.
Transcribed Image Text:Which of the following statements is FALSE? O A successful Claisen condensation requires an ester starting material with at least one alpha hydrogen. O The keto tautomer is usually more stable than the enol tautomer. O In a Claisen condensation, you want to match the alkoxide base with the -OR of the ester in order to avoid unwanted transesterification. O An alpha hydrogen on an ester is less acidic than an alpha hydrogen on an aldehyde. O The base-promoted halogenation of a ketone replaces all of the alpha-hydrogen atoms.
Expert Solution
Step 1

Ketone alpha hydrogen is slightly acidic in nature. This is due to the stabilization of the conjugate base with the carbonyl group. Halogenation of ketone can be promoted with the help of base. In a basic medium, halogenation is taken place. This is particularly a substitution reaction where alpha hydrogen is replaced with a halogen.

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