Dolbier HW Solutions 651

Dolbier HW Solutions 651 - 745 LIPIDS The necessary carbon...

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The necessary carbon carbon bonds can be assembled by the reaction of an ester with two moles of a Grignard reagent. With the correct carbon skeleton in place, all that is needed is to convert the alcohol to the alkene. This can be accomplished by dehydration and reduction. ( d ) Icosanoic acid contains two more carbon atoms than octadecanoic acid. A reasonable approach utilizes a malonic ester synthesis. CH 3 (CH 2 ) 16 CH 2 Br CH 3 (CH 2 ) 16 CH 2 CH(CO 2 CH 2 CH 3 ) 2 CH 2 (CO 2 CH 2 CH 3 ) 2 1 NaOCH 2 CH 3 1-Bromooctadecane [prepared as in part ( a )] Diethyl malonate Diethyl 2-octadecylmalonate CH 3 (CH 2 ) 16 CH 2 CH 2 CO 2 H Icosanoic acid 1. HO 2 , H 2 O 2. H 1 3. heat CH 3 (CH 2 ) 18
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