Dolbier HW Solutions 325

Dolbier HW Solutions 325 - 419 ETHERS, EPOXIDES, AND...

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( d ) Because it gives an epoxide on treatment with a peroxy acid, compound I must be an alkene; more speci f cally, it is 1,2-dimethylcyclopentene. Compounds J and L have the same molecular formula, C 7 H 14 O 2 , but J is a liquid and L is a crys- talline solid. Their molecular formulas correspond to the addition of two OH groups to compound I. Osmium tetraoxide brings about syn hydroxylation of an alkene; therefore com- pound J must be the cis diol. Acid-catalyzed hydrolysis of an epoxide yields a trans diol (compound L): 16.34 Cineole contains no double or triple bonds and therefore must be bicyclic, on the basis of its molecu- lar formula (C 10 H 18 O, index of hydrogen de f ciency 5 2). When cineole reacts with hydrogen chloride, one of the rings is broken and water is formed. The reaction that takes place is hydrogen halide-promoted ether cleavage. In such a reaction with
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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