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Dolbier HW Solutions 468 - 562 CARBOXYLIC ACID DERIVATIVES...

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( j ) A Hofmann rearrangement of benzamide affords aniline. 20.30 The problem speci fi es that is to be prepared from 18 O-labeled ethyl alcohol . Thus, we need to prepare 18 O-labeled ethyl alcohol from the other designated starting materials, acetaldehyde and 18 O-enriched water. First, replace the oxygen of acetaldehyde with 18 O by the hydration dehydration equilibrium in the presence of 18 O-enriched water. Once 18 O-enriched acetaldehyde has been obtained, it can be reduced to 18 O-enriched ethanol. 20.31 ( a ) The rate-determining step in basic ester hydrolysis is nucleophilic addition of hydroxide ion to the carbonyl group. The intermediate formed in this step is negatively charged. The electron-withdrawing effect of a CF 3 group stabilizes the intermediate formed in the rate- determining step of ethyl tri fl uoroacetate saponi fi cation. Because the intermediate is more stable, it is formed faster than the one from ethyl acetate.
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