Ch_322b_19.06

Ch_322b_19.06 - Chapter 19.6 lecture note

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The Malonic Ester Synthesis of Substituted Acetic Acids By a similar sequence of alkylation, hydrolysis, and decarboxylation, substituted acetic acids may be prepared from diethyl malonate . EtOCCH 2 COEt O = O R- CH 2 COOH diethyl malonate alkylated acetic acid malonic ester synthesis
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The Malonic Ester Synthesis EtOCCH 2 COEt O = O diethyl malonate (pK a = 12.9) + NaOEt EtOCCHCOEt O O - Na + + EtOH pK a = 16 enolate anion (stoichiometric amount) formation of enolate anion alkylation EtOCCHCOEt O O - Na + + R-X EtOCCHCOEt O O R + NaX alkylated malonic ester EtOCCHCOEt O O R hydrolysis (i) dil. NaOH, heat (ii) H 3 O + HOCCHCOH O O R alkylated malonic acid HOCCHCOH O O R decarboxylation heat (-CO 2 ) R- CH 2 COOH "alkylated acetic acid"
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Decarboxylation of the malonic acid proceeds via a cyclic transition state that initially produces the enol of the carboxylic acid. C
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Ch_322b_19.06 - Chapter 19.6 lecture note

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