Dolbier HW Solutions 494 - 3 CH 3 CH 2 CH 2 CH 2 CH 2...

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( f ) Treatment of the product of part ( e ) with sodium ethoxide gives an enolate ion that cyclizes by intramolecular nucleophilic substitution of chloride. ( g ) Cyclobutyl methyl ketone is formed by saponi fi cation and decarboxylation of the product in part ( f ). ( h ) Ethyl acetoacetate undergoes Michael addition to phenyl vinyl ketone in the presence of base. ( i ) A diketone results from saponi fi cation and decarboxylation of the Michael adduct. 21.19 Diethyl malonate reacts with the reagents given in the preceding problem in a manner analogous to that of ethyl acetoacetate. ( a ) ( b ) Heptanoic acid Diethyl 1,1-hexanedicarboxylate CH 3 CH 2 CH 2 CH 2 CH 2 CH(COOCH 2 CH 3 ) 2 1. HO , H 2 O 2. H 3. heat CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 COH O 1-Bromopentane Diethyl malonate CH 2 (COOCH 2 CH 3 ) 2 CH 3 CH 2 CH 2 CH 2 CH 2 Br Diethyl 1,1-hexanedicarboxylate (diethyl pentylmalonate) NaOCH
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Unformatted text preview: 3 CH 3 CH 2 CH 2 CH 2 CH 2 CH(COOCH 2 CH 3 ) 2 Ethyl 2-acetyl-5-oxo-5-phenylpentanoate CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CC 6 H 5 O O O 1-Phenyl-1,5-hexanedione CH 3 CCH 2 CH 2 CH 2 CC 6 H 5 O O 1. HO 2 , H 2 O 2. H 1 3. heat 1 Phenyl vinyl ketone Ethyl acetoacetate O CH 3 CCH 2 COCH 2 CH 3 O H 2 C CHCC 6 H 5 O NaOCH 2 CH 3 ethanol Ethyl 2-acetyl-5-oxo-5-phenylpentanoate CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CC 6 H 5 O O O Ethyl 1-acetylcyclobutanecarboxylate O CH 3 C O COCH 2 CH 3 Cyclobutyl methyl ketone O CH 3 C 1. HO 2 , H 2 O 2. H 1 3. heat Ethyl 1-acetylcyclobutanecarboxylate Ethyl 2-acetyl-5-chloropentanoate NaOCH 2 CH 3 CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CH 2 Cl O O O CH 3 C O COCH 2 CH 3 588 ESTER ENOLATES...
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