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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 饾泝- 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

In contrast to the rapid reaction shown in Problem 23-60, ethyl acetoacetate requires a temperature over 150 掳C to undergo the same kind of cleavage reaction. How can you explain the difference in reactivity?

The Darzens reaction involves a two-step, base-catalyzed condensation of ethyl chloroacetate with a ketone to yield an epoxy ester. The first step is a carbonyl condensation reaction, and the second step is an SN2 reaction. Write both steps, and show their mechanisms.

Predict the product(s) and provide the mechanism for each reaction below.

Show how you would synthesize the following compound using an aldol reaction:

The aldol reaction is catalyzed by acid as well as the base. What is the reactive nucleophile in the acid-catalyzed aldol reaction? Propose a mechanism.
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