276 PRACTICAL ORGANIC CHEMISTRY It follows therefore that ethyl malonate can be used (just as ethyl aceto-acetate) to prepare any mono- or di-substituted acetic acid: the limitations are identical, namely the substituents must necessarily be alkyl groups (or aryl-alkyl groups such as C 6 H 6 CH 2 ), and tri-substituted acetic acids cannot be prepared. Ethyl malonate undergoes no reaction equivalent to the ketonic hydrolysis of ethyl acetoacetate, and the concentration of the alkali used for the hydrolysis is therefore not important. Ethane Tetracarboxylic Ethyl Ester. (C 2 H 5 OOC) 2 CH-CH(COOC 2 H 5 ) 2 . When an ethanolic solution of the sodium derivative of ethyl malonate is shaken with a solution of iodine, the latter withdraws the sodium, and the ethyl malonate residues link together in pairs to give the tetra-ethyl ester of XaCH(COOC 2 HJ 2 CH(COOC 2 H 6 ) 2 I, r""'" I + 2NaI NaCH(COOC 2 H-,), CH(COOC 2 H 6 ) 2 syw-ethane tetracarboxylic acid. Required:
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.