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Unformatted text preview: The end result is the same with formation of more enolate anion of the diethyl malonate to drive along the conjugate addition reaction. conjugate addition of enolate anion + :CH(COOEt) 2 CH 3 C=CH-COEt CH 3 O =-CH 3 C-CH CH 3 CH(COOEt) 2 COEt O-enolate anion of ester proton transfer and trapping of enolate anion CH 3 C-CH CH 3 CH(COOEt) 2 COEt O-+ EtOH CH 3 C-CH 2-COEt CH 3 CH(COOEt) 2-O + EtO base is reformed. Further Synthetic Modifications Alkaline hydrolysis and heating to induce decarboxylation of the malonic acid subunit yields 3,3-dimethylglutaric acid . CH 3 C-CH 2-COEt CH 3 CH(COOEt) 2 O = (i) dil NaOH, heat (ii) H 3 O + CHCCH 2 COOH CH 3 CH 3 HOOC HOOC CH CCH 2 COOH CH 3 CH 3 HOOC HOOC heat &gt;100 o C (-CO 2 ) HOOCCH 2 CCH 2 COOH CH 3 CH 3 3,3-dimethylglutaric acid...
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- Organic chemistry