Dolbier HW Solutions 503

Dolbier HW Solutions 503 - 2 , H 2 O 2. H 1 3. heat HOCCH 2...

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( f ) Cyclopropanecarboxylic acid may be prepared by a malonic ester synthesis, as retrosynthetic analysis shows. The desired reaction sequence is ( g ) Treatment of the diester formed in part ( f ) with ammonia gives a diamide. ( h ) We need to extend the carbon chain of the starting material by four carbons. One way to accomplish this is by way of a malonic ester synthesis at each end of the chain. 21.26 The problem states that diphenadione is prepared from 1,1-diphenylacetone and dimethyl 1,2- benzenedicarboxylate. Therefore, disconnect the molecule in a way that reveals the two reactants. and CH 3 CCH(C 6 H 5 ) 2 O CX CX O O CCH(C 6 H 5 ) 2 O O O Diphenadione 1 NaOCH 2 CH 3 2CH 2 (COOCH 2 CH 3 ) 2 Diethyl malonate Br(CH 2 ) 8 Br 1,8-Dibromooctane (CH 3 CH 2 OOC) 2 CH(CH 2 ) 8 CH(COOCH 2 CH 3 ) 2 1. HO
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Unformatted text preview: 2 , H 2 O 2. H 1 3. heat HOCCH 2 (CH 2 ) 8 CH 2 COH O O Dodecanedioic acid 1. LiAlH 4 2. H 2 O Octanedioic acid HOC(CH 2 ) 6 COH O O HOCH 2 (CH 2 ) 6 CH 2 OH 1,8-Dibromooctane BrCH 2 (CH 2 ) 6 CH 2 Br HBr or PBr 3 NH 3 COCH 2 CH 3 COCH 2 CH 3 O O Diethyl cyclopropane-1,1-dicarboxylate [prepared as in part ( f )] CNH 2 CNH 2 O O Cyclopropane-1,1-dicarboxamide 1 COOCH 2 CH 3 COOCH 2 CH 3 NaOCH 2 CH 3 ethanol 1. HO 2 , H 2 O 2. H 1 3. heat CH 2 (COOCH 2 CH 3 ) 2 Diethyl malonate BrCH 2 CH 2 Br 1,2-Dibromoethane COH O Cyclopropane-carboxylic acid CH 2 (CO 2 CH 2 CH 3 ) 2 1 CH 2 X CH 2 X CO 2 H CO 2 CH 2 CH 3 CO 2 CH 2 CH 3 ESTER ENOLATES 597...
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