The necessary carbon–carbon bonds can be assembled by the reaction of an ester with twomoles of a Grignard reagent.With the correct carbon skeleton in place, all that is needed is to convert the alcohol to thealkene. 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.CH3(CH2)16CH2BrCH3(CH2)16CH2CH(CO2CH2CH3)2CH2(CO2CH2CH3)21NaOCH2CH31-Bromooctadecane[prepared as in part (a)]Diethyl malonateDiethyl 2-octadecylmalonateCH3(CH2)16CH2CH2CO2HIcosanoic acid1. HO2, H2O2. H13. heatCH3(CH2)18
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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.