Ch_322b_19.01

Ch_322b_19.01 - of enolate anions in solution. -C-C-C-:O:...

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Chapter 19 Synthesis and Reactions of ! -Dicarbonyl Compounds: Enolate Ions This group of compounds includes: ! -Dicarbonyl Compounds: -C-CH 2 -C- O = O " ! RCCH 2 COR' O O ! -keto esters ROCCH 2 COR O O malonic esters
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These compounds are widely used in organic synthesis because of the stability of the anion formed by loss of the relatively acidic enolizable H : The synthetic importance of these enolate anions derives from the participation of the nucleophilic carbanion in a variety of carbon-carbon bond forming condensation reactions. -C-C-C- :O: = :O: H pK a 9-11 ~ ~ + B: - Bases such as alkoxides react completely with ! -dicarbonyl compounds to produce stoichiometric quantities
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Unformatted text preview: of enolate anions in solution. -C-C-C-:O: :O: :--C-C=C-:O: :O:--C=C-C-:O:-:O: resonance stabilized enolate anion-C C C-O O !" !" !" enolate anion hybrid Facile Decarboxylation of !-keto Acids A second feature built into many synthetic applications of !-keto esters is the facile decarboxylation of the corresponding !-keto acids:-C-C-CO 2 R O = !-keto ester hydrolysis-C-C-CO 2 H O !-keto acid heat-C-C-H O ketone + CO 2 Quiz 19.01 The acidity order (strongest to weakest) of the indicated H in the compounds below is CH 3 CH 2 O H EtOOCC H 2 COOEt C H 3 COOEt I II III > > II I III...
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Ch_322b_19.01 - of enolate anions in solution. -C-C-C-:O:...

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