(b)Carbon–carbon triple bonds are converted to trans alkenes by reduction with lithium andammonia.(c)The carbon–carbon double bond is hydrogenated readily over a platinum catalyst. Reductionof the ester function does not occur.(d)Lithium aluminum hydride reduces the ester function but leaves the carbon–carbon doublebond intact.(e)Epoxidation of the double bond occurs when an alkene is treated with a peroxy acid. Thereaction is stereospecifc; substituents that are cis to each other in the alkene remain cis in theepoxide.(f)Acid-catalyzed hydrolysis of the epoxide yields a diol; its stereochemistry corresponds to netanti hydroxylation of the double bond of the original alkene.The product is chiral but is formed as a racemic mixture containing equal amounts of the9R,10Rand 9S,10Sstereoisomers when the starting epoxide is racemic.9,10-Dihydroxyoctadecanoic acidC(CH2)7COOHHOHHCH3(CH2)7OHH3O1Ccis-9,10-Epoxyoctadecanoic acid
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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.