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Sia

青州's Question
Chemistry
Posted 7 months ago

Draw this reaction's mechanism.
(It is hydrolysis.)
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Answer from Sia
Posted 7 months ago
Solution
1
Protonation of the carbonyl oxygen: The first step in the hydrolysis mechanism involves the protonation of the carbonyl oxygen of the amide. This is facilitated by the acidic conditions provided by methanol. The protonation increases the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack
2
Nucleophilic attack by methanol: Methanol acts as a nucleophile and attacks the electrophilic carbonyl carbon, leading to the formation of a tetrahedral intermediate
3
Proton transfer: A proton is transferred from the methanol oxygen to the nitrogen atom, which helps to stabilize the tetrahedral intermediate
4
Collapse of the tetrahedral intermediate: The tetrahedral intermediate collapses, and the nitrogen-carbonyl bond is broken. This results in the formation of a carbamic acid intermediate and the expulsion of the "cbz" protected amine
5
Decomposition of carbamic acid: The carbamic acid intermediate decomposes to release carbon dioxide (CO2CO_2) and form the final product, which is the amine with a hydroxyl group attached to the nitrogen atom
Answer
The mechanism of the hydrolysis reaction involves protonation of the carbonyl oxygen, nucleophilic attack by methanol, proton transfer, collapse of the tetrahedral intermediate, and decomposition of carbamic acid to release CO2CO_2 and form the final product.
Key Concept
Hydrolysis of an amide under acidic conditions
Explanation
The reaction proceeds through a series of steps starting with protonation, followed by nucleophilic attack, proton transfer, intermediate collapse, and decomposition to yield the hydrolyzed product.

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