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Chapter 23: Q59E (page 783)

In the mixed Claisen reaction of cyclopentanone with ethyl format, a much higher yield of the desired product is obtained by first mixing the two carbonyl components and then adding a base, rather than by first mixing base with cyclopentanone and then adding ethyl format. Explain.

Short Answer

Expert verified

Claisen condensation reaction occurs at a much faster rate without any competition with the self-aldol reaction when we add ethyl format first.

Step by step solution

01

Claisen condensation

Claisen condensationoccurs between two ester compounds in the presence of a strong base which gives 𝛃- keto ester product and alcohol generally.

02

The reason for the above case:

If we add base first then cyclopentanone can undergo self-aldol condensation and does not give desired product but when we add ethyl format first then the self-aldol condensation does not occur and it gives a mixed Claisen condensation reaction with a much faster rate without any competition with self-aldol reaction.

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Most popular questions from this chapter

How might the following compounds be prepared using Michael reactions? Show the nucleophilic donor and the electrophilic acceptor in each case.

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