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by: Carmela Kilback


Carmela Kilback
GPA 3.92

Tomikazu Sasaki

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Tomikazu Sasaki
Class Notes
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This 13 page Class Notes was uploaded by Carmela Kilback on Wednesday September 9, 2015. The Class Notes belongs to CHEM 239 at University of Washington taught by Tomikazu Sasaki in Fall. Since its upload, it has received 23 views. For similar materials see /class/192561/chem-239-university-of-washington in Chemistry at University of Washington.




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Date Created: 09/09/15
Chem 239 ESTER ENOLATES The nature of BKeto esters Importance of BKeto esters Claisen condensation Reaction Mechanism Intramolecular The Dieckmann Reaction Mixed substrates Acylation of ketones with esters Ketone synthesis Via BKeto esters Acetoacetic ester synthesis to Ketones Malonic ester synthesis to Carboxylic acids Barbiturates Michael additions of anions ocDeprotonation of carbonyl compounds Reading Pg 886905 Problems 2116 2117 2122 2130 Claisen condensation O O R C C OR C H 2 esters ocsubstituted Intramolecular Mixed esters O 0 CH3 C CH3 C 0 CH2 CH3 0 CH2 CH3 1 NaOCH2CH3 0 CH3 c 0 CH2 CH3 O CmC 0 CH2 CH3 2 H3O 0 0 CH3 C CH3 C 0 CH2 CH3 ocsubstituted O esters CH32CH C O 0 CH2 CH3 CH32CH C 0 CH2 CH3 1 NaOCH2CH3 0 CH32CH C Q 0 CH2 CH3 O Gw C O CHZ CH3 2 H3O 0 0 CH32CH c CH3CH3 0 CH2 CH3 Intramolecular Claisen Condensation Dieckmann cyclization O CHZ C CH2 0 CH2 CH3 CH 2 0 0 CH2 CH3 Diethylhexanedioate O H 0 O C 0 CH2 CH3 Mixed Claisen condensation 0 O CH32CHC 0 CH2 CH3 H C 0 CH2 CH3 1 NaOCH2CH3 0 H C Q 0 CH2 CH3 O CH32C C O CHZ CH3 2 H3O 0 O H C CH3CH3 0 CH2 CH3 Innert esters for mixed condensations 0 H C O R Formate esters Carbonate esters Oxalate esters Benzoate esters R C C R C R H Acylation of ketones 1 Diones 2 Bketo esters 3 Monoketones Acylation of ketones with esters 0 0 R C CH3 RO C Esters R O 0 R C CH3 R Acylation of ketones with esters O 0 R C CHZR RO C Carbonate O R esters O 0 R C CH O R Ra Ketone synthesis via 3 keto esters O O C k H RC CH OR B eto esters R 1 KOH H20 70800C v 2 H3O 1 70800C 2 39C02 0 R 393 CH monoketone 2 Ketone synthesis via 3 keto esters Alkylation of acetoacetic esters O O R c C OCHZCH3 R X CH sN2 O I 1 KOH H20 70800C R C CH2 2 H 0 R9 3 1 70800C 2 39C02


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