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Chapter 23: Q15P (page 770)

Dieckmann cyclization of diethyl 3-methylheptanedioate gives a mixture of two𝛃-keto ester products. What are their structures, and why is a mixture formed?

Short Answer

Expert verified

WhenDieckmann cyclizationof diethyl 3-methylheptanedioate occurs, it forms a mixture of two 𝛃-keto ester products because it is an unsymmetrical diester compound.

Step by step solution

01

Mechanism of Dieckmann cyclization of diethyl 3-methylheptanedioate

02

Conclusion

Since diethyl 3-methylheptanedioate is an unsymmetrical diester compoundso it can form two enolates compounds and each can cyclize to give two 𝛃-keto ester products.

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