Dolbier HW Solutions 648

Dolbier HW Solutions 648 - 742 LIPIDS(b Carboncarbon triple...

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( b ) Carbon carbon triple bonds are converted to trans alkenes by reduction with lithium and ammonia. ( c ) The carbon carbon double bond is hydrogenated readily over a platinum catalyst. Reduction of the ester function does not occur. ( d ) Lithium aluminum hydride reduces the ester function but leaves the carbon carbon double bond intact. ( e ) Epoxidation of the double bond occurs when an alkene is treated with a peroxy acid. The reaction is stereospeci f c; substituents that are cis to each other in the alkene remain cis in the epoxide. ( f ) Acid-catalyzed hydrolysis of the epoxide yields a diol; its stereochemistry corresponds to net anti hydroxylation of the double bond of the original alkene. The product is chiral but is formed as a racemic mixture containing equal amounts of the 9 R ,10 R and 9 S ,10 S stereoisomers when the starting epoxide is racemic. 9,10-Dihydroxyoctadecanoic acid C (CH 2 ) 7 COOH HO H H CH 3 (CH 2 ) 7 OH H 3 O 1 C cis -9,10-Epoxyoctadecanoic acid
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