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N-Acetylazoles undergo hydrolysis more readily than
Chapter 21, Problem 21.82(choose chapter or problem)
QUESTION:
N-Acetylazoles undergo hydrolysis more readily than regular amides. Suggest a reason for the enhanced reactivity of N-acetylazoles toward nucleophilic acyl substitution:
Questions & Answers
QUESTION:
N-Acetylazoles undergo hydrolysis more readily than regular amides. Suggest a reason for the enhanced reactivity of N-acetylazoles toward nucleophilic acyl substitution:
ANSWER:Step 1 of 3
In normal amides, the lone pair of nitrogen atom connected to the carbonyl group can donate significant electrons density to the carbonyl carbon. This decreases the partial positive charge character on carbonyl carbons, which lowers the rate of hydrolysis as the water nucleophile is less attracted to that particular atom.