Dolbier HW Solutions 493

Dolbier HW Solutions 493 - CH 3 CCCOOCH 2 CH 3 CH 2 CH 2 CH...

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21.18 ( a ) Ethyl acetoacetate is converted to its enolate ion with sodium ethoxide; this anion then acts as a nucleophile toward 1-bromopentane. ( b ) Saponi f cation and decarboxylation of the product in part ( a ) yields 2-octanone. ( c ) The product derived from the reaction in part ( a ) can be alkylated again: ( d ) The dialkylated derivative of acetoacetic ester formed in part ( c ) can be converted to a ketone by saponi f cation and decarboxylation. ( e ) The anion of ethyl acetoacetate acts as a nucleophile toward 1-bromo-3-chloropropane. Bromide is a better leaving group than chloride and is displaced preferentially. 1-Bromo-3- chloropropane Ethyl acetoacetate 1 BrCH 2 CH 2 CH 2 Cl Ethyl 2-acetyl-5-chloropentanoate O CH 3 CCH 2 COCH 2 CH 3 O NaOCH 2 CH 3 CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CH 2 Cl O O Ethyl 2-acetyl-2-methylheptanoate
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Unformatted text preview: CH 3 CCCOOCH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 OCH 3 3-Methyl-2-octanone CH 3 CCHCH 3 CH 2 CH 2 CH 2 CH 2 CH 3 O 1. HO 2 , H 2 O 2. H 1 3. heat Ethyl 2-acetyl-2-methylheptanoate NaOCH 2 CH 3 CH 3 CCCOOCH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 OCH 3 Ethyl 2-acetylheptanoate CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 O O 1 CH 3 I Ethyl 2-acetylheptanoate 2-Octanone CH 3 CCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 O O CH 3 CCHCOCH 2 CH 3 O (CH 2 ) 4 CH 3 1. HO 2 , H 2 O 2. H 1 3. heat O 1-Bromopentane Ethyl acetoacetate 1 CH 3 CCH 2 COCH 2 CH 3 CH 3 CH 2 CH 2 CH 2 CH 2 Br Ethyl 2-acetylheptanoate O NaOCH 2 CH 3 CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 O O ESTER ENOLATES 587...
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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