What Problem Is Encountered in the Synthesis of Ethyl Acetoacetate

question 27

Multiple Choice

What problem is encountered in the synthesis of ethyl acetoacetate (shown below) if sodium methoxide is used rather than sodium ethoxide?

• A) Sodium methoxide is too weak a base to cause this reaction to occur.
• B) The condensation proceeds further to give tri-carbonyl products.
• C) The reaction would produce some of both the methyl ester and the ethyl ester.
• D) Sodium methoxide is too insoluble in methanol to promote the reaction.
• E) Sodium methoxide is not basic enough to drive the reaction to completion.

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