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What will be the product of a nucleophilic
Chapter 16, Problem 15P(choose chapter or problem)
Problem 15P
What will be the product of a nucleophilic addition–elimination reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following?
a. a stronger base than the substituent that was attached to the acyl group
b. a weaker base than the substituent that was attached to the acyl group
c. similar in basicity to the substituent that was attached to the acyl group
Questions & Answers
QUESTION:
Problem 15P
What will be the product of a nucleophilic addition–elimination reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following?
a. a stronger base than the substituent that was attached to the acyl group
b. a weaker base than the substituent that was attached to the acyl group
c. similar in basicity to the substituent that was attached to the acyl group
ANSWER:
Solution 15P
(a)
The mechanism for the nucleophilic addition-elimination reactions involves the formation of a tetrahedral intermediate.
In the intermediate, the weaker of the two bases is eliminated. Because a stronger base is added, the group attached to the acyl group in the reactant is eliminated.
This results in the formation of a carboxylic acid derivative.