1.) Chlorotrimethylsilane reacts with enolate anions to form stable
ethers. For example (see reaction below) 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? Whould 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?
CH3
:O:
(CH3)3SiCl
(C2H5)3N:
HCON(CH3)2
CH3
:O:
:O:
CH3
+
Double Bond Here
Double Bond Here
Chemistry Homework Solutions
#43804
Chlorotrimethylsilane reacts with enolate anions...
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? Whould 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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