Dolbier HW Solutions 502

Dolbier HW Solutions 502 - 2 CH 2 CCH 3 H 2 C 1 CHCH 2 X H...

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( c ) In this synthesis the desired 1,3-diol function can be derived by reduction of a malonic ester derivative. First propene must be converted to an allyl halide for use as an alkylating agent. ( d ) The desired primary alcohol may be prepared by reduction of the corresponding carboxylic acid, which in turn is available from the malonic ester synthesis using allyl chloride, includ- ing saponi f cation and decarboxylation of the diester [prepared in part ( c )]. The correct sequence of reactions is ( e ) The desired product is an alcohol. It can be prepared by reduction of a ketone, which in turn can be prepared by the acetoacetic ester synthesis. Therefore 1. HO 2 , H 2 O CH 2 O CH 3 CCH 2 CH 2 CH NaBH 4 CH 3 OH CH 2 OH CH 3 CHCH 2 CH 2 CH 5-Hexen-2-ol 1 CH 2 CH 2 CH CH 3 CCHCOCH 2 CH 3 O O NaOCH 2 CH 3 ethanol CHCH 2 Cl H 2 C Allyl chloride CH 3 CCH 2 COCH 2 CH 3 O O Ethyl acetoacetate 2. H 1 3. heat CHCH 2 CH 2 CHCH 3 OH H 2 C O CHCH
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Unformatted text preview: 2 CH 2 CCH 3 H 2 C 1 CHCH 2 X H 2 C O CH 2 CCH 3 2 CHCH 2 CH(COOCH 2 CH 3 ) 2 H 2 C Diethyl 2-allylmalonate [prepared as in part ( c )] CHCH 2 CH 2 COOH H 2 C 4-Pentenoic acid CHCH 2 CH 2 CH 2 OH H 2 C 4-Penten-1-ol 1. HO 2 , H 2 O 2. H 1 3. heat 1. LiAlH 4 2. H 2 O CHCH 2 CH 2 CH 2 OH H 2 C CHCH 2 CH 2 CO 2 H H 2 C CHCH 2 CH(CO 2 CH 2 CH 3 ) 2 H 2 C 4-Penten-1-ol NaOCH 2 CH 3 ethanol CHCH 2 Cl H 2 C Allyl chloride 1 CH 2 (COOCH 2 CH 3 ) 2 Diethyl malonate CHCH 2 CH(COOCH 2 CH 3 ) 2 H 2 C Diethyl 2-allylmalonate CHCH 2 CH(CH 2 OH) 2 H 2 C 2-Allyl-1,3-propanediol 1. LiAlH 4 2. H 2 O Cl 2 heat CHCH 3 H 2 C Propene CHCH 2 Cl H 2 C Allyl chloride CHCH 2 CH(CH 2 OH) 2 H 2 C CHCH 2 X H 2 C 1 CH(COOCH 2 CH 3 ) 2 2 596 ESTER ENOLATES...
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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