Dolbier HW Solutions 498

Dolbier HW Solutions 498 - 2 O 2. H 1 3. heat O C CH 2...

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( e ) An alkylated derivative of ethyl acetoacetate is capable of being alkylated a second time. ( f ) The dialkylated derivative of acetoacetic ester formed in part ( e ) is converted to a ketone by saponi f cation and decarboxylation. ( g ) The enolate of acetophenone attacks the carbonyl group of diethyl carbonate. ( h ) Diethyl oxalate acts as an acylating agent toward the enolate of acetone. ( i ) The f rst stage of the malonic ester synthesis is the alkylation of diethyl malonate with an alkyl halide. ( j ) Alkylation of diethyl malonate is followed by saponi f cation and decarboxylation to give a carboxylic acid. ( k ) The anion of diethyl malonate undergoes Michael addition to 6-methyl-2-cyclohexenone. CH 2 (COOCH 2 CH 3 ) 2 NaOCH 2 CH 3 ethanol 1 O H 3 C O H 3 C CH(COOCH 2 CH 3 ) 2 Diethyl malonate 6-Methyl-2- cyclohexenone Diethyl 2-(4-methyl-3-oxocyclohexyl)malonate (isolated yield, 50%) CH 3 CH 2 CHCH 2 CH(COOCH 2 CH 3 ) 2 Diethyl 3-methylpentane-1,1-dicarboxylate 4-Methylhexanoic acid (57% yield from 1-bromo-2-methylbutane) CH 3 CH 3 CH 2 CHCH 2 CH 2 COH CH 3 1. NaOH, H
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Unformatted text preview: 2 O 2. H 1 3. heat O C CH 2 (COOCH 2 CH 3 ) 2 CH 3 CH 2 CHCH 2 CH(COOCH 2 CH 3 ) 2 BrCH 2 CHCH 2 CH 3 1 NaOCH 2 CH 3 ethanol Diethyl malonate 1-Bromo-2-methylbutane Diethyl 3-methylpentane-1,1-dicarboxylate CH 3 CH 3 Ethyl 2,4-dioxopentanoate CH 3 CCH 2 CCOCH 2 CH 3 O O O Diethyl oxalate CH 3 CH 2 OCCOCH 2 CH 3 O O Acetone CH 3 CCH 3 O 1 1. NaOCH 2 CH 3 2. H 1 3-Oxo-3-phenylpropanoate C 6 H 5 CCH 2 COCH 2 CH 3 O O Diethyl carbonate CH 3 CH 2 OCOCH 2 CH 3 O Acetophenone C 6 H 5 CCH 3 O 1 1. NaOCH 2 CH 3 2. H 1 3-Butyl-2-heptanone CH 3 CCH(CH 2 CH 2 CH 2 CH 3 ) 2 O Ethyl 2-acetyl-2-butylhexanoate CH 3 CC(CH 2 CH 2 CH 2 CH 3 ) 2 COOCH 2 CH 3 O 1. NaOH 2. H 1 3. heat 1-Iodobutane CH 3 CH 2 CH 2 CH 2 I 1 NaOCH 2 CH 3 ethanol Ethyl 2-acetylhexanoate CH 3 CCHCOCH 2 CH 3 CH 2 CH 2 CH 2 CH 3 O O Ethyl 2-acetyl-2-butylhexanoate CH 3 CC(CH 2 CH 2 CH 2 CH 3 ) 2 COOCH 2 CH 3 O 592 ESTER ENOLATES...
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