(a)
Interpretation:
The complete and detailed mechanism for the given reaction is to be drawn, and the overall product of the reaction is to be predicted.
Concept introduction:
This is saponifiaction reaction. A
The irreversible deprotonation in Step 3 makes the overall saponification reaction irreversible. The initial carboxylic acid is produced reversibly, but it is continually removed via Step 3, which helps drive the reaction to completion.
(b)
Interpretation:
The complete and detailed mechanism for the given reaction is to be drawn, and the overall product of the reaction is to be predicted.
Concept introduction:
This is saponifiaction reaction. A carboxylic acid is produced when an ester undergoes saponification, followed by acid workup. Steps 1 and 2 are identical to the nucleophilic addition and elimination steps. Step 3 is the rapid, irreversible deprotonation of the newly formed carboxylic acid. Finally, the proton is replenished by adding a strong acid.
The irreversible deprotonation in Step 3 makes the overall saponification reaction irreversible. The initial carboxylic acid is produced reversibly, but it is continually removed via Step 3, which helps drive the reaction to completion.
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Chapter 20 Solutions
ORGANIC CHEMISTRY:PRINCIPLES...(PB)
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