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Dolbier HW Solutions 649 - 743 LIPIDS(g Hydroxylation of...

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( g ) Hydroxylation of carbon carbon double bonds with osmium tetraoxide proceeds with syn ad- dition of hydroxyl groups. The product is chiral but is formed as a racemic mixture containing equal amounts of the 9 R ,10 S and 9 S ,10 R stereoisomers. ( h ) Hydroboration oxidation gives syn hydration of carbon carbon double bonds with a regio- selectivity contrary to Markovnikov s rule. The reagent attacks the less hindered face of the double bond of -pinene. ( i ) The starting alkene in this case is -pinene. As in the preceding exercise with -pinene, diborane adds to the bottom face of the double bond. ( j ) The starting material is an acetal. It undergoes hydrolysis in dilute aqueous acid to give a
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