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Unformatted text preview: a ~ 11) are produced in stoichiometric amounts by reaction with alkoxide bases. C O = CH 2 O C pK a ~ ~ 11 + NaOEt C O CH O C :-Na + + EtO H pK a = 16 stoichiometric concentration essentially complete reaction Alkylation of the Enolate Anion After formation of one full equivalent of the enolate anion, one equivalent of an alkylating agent (RX) is added: C O CH O C-Na + + R-X S N 2 C O C O C H R + NaX alkylated product Two 1,3-dicarbonyl compounds that are classic examples of the synthetic applications of this chemistry are: Two standard syntheses developed many years ago that exploit the extraordinary stability of enolate anions derived from 1,3-dicarbonyl compounds are: C O = CH 2 O C CH 3 C 2 H 5 O ethyl acetoacetate (pK a = 10.7) C O CH 2 O C C 2 H 5 O C 2 H 5 O diethyl malonate (pK a = 12.9) (1) The acetoacetic ester synthesis of substituted acetones (2) The malonic ester synthesis of substituted acetic acids...
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.
- Organic chemistry