Dolbier HW Solutions 357

Dolbier HW Solutions 357 - 451 ALDEHYDES AND KETONES...

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17.33 ( a ) The bacterial enzyme cyclohexanone monooxygenase was described in Section 17.16 as able to catalyze a biological Baeyer Villiger reaction. Compound A is 4-methylcyclohexanone. ( b ) The product of Baeyer Villiger oxidation of 4-methylcyclohexanone with peroxyacetic acid would be the racemic cyclic ester (lactone), not the single enantiomer shown in part ( a ) from the enzyme-catalyzed oxidation. 17.34 ( a ) Nucleophilic ring opening of the epoxide occurs by attack of methoxide at the less hindered carbon. The anion formed in this step loses a chloride ion to form the carbon oxygen double bond of the product. ( b ) Nucleophilic addition of methoxide ion to the aldehyde carbonyl generates an oxyanion, which can close to an epoxide by an intramolecular nucleophilic substitution reaction. The epoxide formed in this process then undergoes nucleophilic ring opening on attack by a
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