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Which statements are true for the mechanism for hydrolysis of an amide? * tthe reaction is a nucleophilic acyl addition. Water acts as the nucleophile in hydrolysis. The mechanism involves six steps. Protonating the carbonyl oxygen speeds up hydrolysis. Protonating the amino group creates a better leaving group by weakening the carbon-nitrogen bond.
Accepted Answer
The following statements are true for the mechanism of amide hydrolysis:
The reaction is a nucleophilic acyl addition. This is correct. The nucleophile attacks the carbonyl carbon of the amide, leading to the formation of a tetrahedral intermediate.
Water acts as the nucleophile in hydrolysis. This is also correct. Water is the nucleophile that attacks the carbonyl carbon.
Protonating the carbonyl oxygen speeds up hydrolysis. This is true. Protonating the carbonyl oxygen makes the carbonyl carbon more electrophilic, increasing the rate of nucleophilic attack.
Protonating the amino group creates a better leaving group by weakening the carbon-nitrogen bond. This is correct. Protonation of the amino group makes it a better leaving group, facilitating the breaking of the carbon-nitrogen bond in the final step.
The statement about the mechanism involving six steps is incorrect. Amide hydrolysis typically involves a four-step mechanism: nucleophilic attack, tetrahedral intermediate formation, proton transfer, and leaving group departure.
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