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    stability of enols of beta-dicarbonyl compounds

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    1.) Chlorotrimethylsilane reacts with enolate anions to form stable ethers. For example (see reaction attached) Assuming that the reaction is run under equilibrium conditions predict which of the silyl enol ethers below is formed in the largest amount and why?

    2.) There are two reasons why the enols of beta-dicarbonyl compounds such as pentane-2,4-dione are relatively stable. One is that they are conjugated and pi-electron overlap due to the conjugation provides additional stability. What is the other reason that these species are relatively stable? Would you expect the enol of cyclohexane-1,3-dione to be as stable as the enol of pentane-2,4-dione? Why or why not?

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    Solution Summary

    The stability of enols of beta-dicarbonyl compounds is discussed.