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PROBLEM 22.29 Complete the following reactions. Assume that one equivalent of NaOEt is present in each case. (a) 3D НС—С—СМes + EtO-С-ОEt NaOEt H,O+ (excess)

PROBLEM 22.29 Complete the following reactions. Assume that one equivalent of NaOEt is present in each case. (a) 3D НС—С—СМes + EtO-С-ОEt NaOEt H,O+ (excess)

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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29(a)
ester ethyl acetate. In fact do not interfere. The analysis of these cases agar carbonyl-compound reactivity. In Eq. 22.66, a possible side reaction is the aldol addition of cyclohera. However, the equilibrium for the aldol addition of two ketones favors the rec the Claisen condensation is irreversible because one equivalent of base is enolate ion of the product, Because the ester has no a-hydrogens, it canne itself. The ester in Eg, 22.67, however, does have a-hydrogens and is known itself (Eq. 22.58, p. 1133). Why is such a condensation not an interfering s answer is that ketones are far more acidic than esters (by about 5–7 pK. uni 22.4 on p. 1104). Thus, the enolate ion of the ketone is formed in much gres than the enolate ion of the ester. The ketone enolate ion can react with an ketone-an unfavorable equilibrium-or it can be intercepted by the exce to give the observed product, which is a B-diketone. Even though ester than ketones, a B-diketone is especially acidic (like a ß-keto ester) and is by the one equivalent of NaOEt. (Be sure to identify the acidic hydrogen Eq. 22.67.) Hence, B-diketone formation is observed because ionization versible reaction. These examples illustrate that the crossed Claisen condensation synthesis of a wide variety of B-dicarbonyl compounds. 2olide PROBLEM 22.29 Complete the following reactions, Assume that one equivalent of NaOEt is present in each case. (а) H3C-C-CMe, + EtO-C: H3O+ NaOEt OEt (еxcess) (b) O Ph-C-CH, + Ph-C- OEt NaOEt H;o+ (excess) (c) O Me Me CO,Et Nall (CH16O4) CO,EL D. Synthesis with the Claisen Condensation As the examples in the previous sections have shown, the Claisen reactions can be used for the synthesis of B-dicarbonyl compounds: E and the like. Compare these types of compounds with those prepar tion, and notice carefully the differences. In planning the synthesis of a B-dicarbonyl compound, we strategy: examine the target molecule and work backward to rea:
Transcribed Image Text:ester ethyl acetate. In fact do not interfere. The analysis of these cases agar carbonyl-compound reactivity. In Eq. 22.66, a possible side reaction is the aldol addition of cyclohera. However, the equilibrium for the aldol addition of two ketones favors the rec the Claisen condensation is irreversible because one equivalent of base is enolate ion of the product, Because the ester has no a-hydrogens, it canne itself. The ester in Eg, 22.67, however, does have a-hydrogens and is known itself (Eq. 22.58, p. 1133). Why is such a condensation not an interfering s answer is that ketones are far more acidic than esters (by about 5–7 pK. uni 22.4 on p. 1104). Thus, the enolate ion of the ketone is formed in much gres than the enolate ion of the ester. The ketone enolate ion can react with an ketone-an unfavorable equilibrium-or it can be intercepted by the exce to give the observed product, which is a B-diketone. Even though ester than ketones, a B-diketone is especially acidic (like a ß-keto ester) and is by the one equivalent of NaOEt. (Be sure to identify the acidic hydrogen Eq. 22.67.) Hence, B-diketone formation is observed because ionization versible reaction. These examples illustrate that the crossed Claisen condensation synthesis of a wide variety of B-dicarbonyl compounds. 2olide PROBLEM 22.29 Complete the following reactions, Assume that one equivalent of NaOEt is present in each case. (а) H3C-C-CMe, + EtO-C: H3O+ NaOEt OEt (еxcess) (b) O Ph-C-CH, + Ph-C- OEt NaOEt H;o+ (excess) (c) O Me Me CO,Et Nall (CH16O4) CO,EL D. Synthesis with the Claisen Condensation As the examples in the previous sections have shown, the Claisen reactions can be used for the synthesis of B-dicarbonyl compounds: E and the like. Compare these types of compounds with those prepar tion, and notice carefully the differences. In planning the synthesis of a B-dicarbonyl compound, we strategy: examine the target molecule and work backward to rea:
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