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Dolbier HW Solutions 311

Dolbier HW Solutions 311 - 405 ETHERS EPOXIDES AND SULFIDES...

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substitution with retention of con f guration, which is not the normal mode of epoxide ring opening. 16.14 Acid-catalyzed nucleophilic ring opening proceeds by attack of methanol at the more substituted carbon of the protonated epoxide. Inversion of con f guration is observed at the site of attack. The correct product is compound A. The nucleophilic ring openings in both this problem and Problem 16.13 occur by inversion of con f guration. Attack under basic conditions by methoxide ion, however, occurs at the less hindered carbon of the epoxide ring, whereas attack by methanol under acid-catalyzed conditions occurs at the more substituted carbon. 16.15 Begin by drawing meso -2,3-butanediol, recalling that a meso form is achiral. The eclipsed confor- mation has a plane of symmetry. Epoxidation followed by acid-catalyzed hydrolysis results in anti addition of hydroxyl groups to the double bond. trans -2-Butene is the required starting material.
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