(a)
Interpretation:
The complete and detailed mechanism of the given reaction is to be drawn, and the product is to be predicted.
Concept introduction:
There are two locations in an
Answer to Problem 18.6P
The product of given reaction is
The mechanism is drawn as
Explanation of Solution
Even though
The negatively charged oxygen extracts a proton from the solvent molecule (
The enol form being relatively unstable rapidly tautomerizes to the more stable keto form of the product.
Thus, the final product of the reaction is
And the complete mechanism can be drawn as
The mechanism and the product of the given reaction were determined on the basis of reversible addition of cyanide ion to the
(b)
Interpretation:
The complete and detailed mechanism of the given reaction is to be drawn, and the product is to be predicted.
Concept introduction:
There are two locations in an
Answer to Problem 18.6P
The product of the given reaction is
The mechanism is drawn as
Explanation of Solution
Two proton transfer steps follow and produce an uncharged enol. The enol form is relatively unstable and rapidly tautomerizes to the more stable keto form.
Thus, the final product of the reaction is
And the complete mechanism can be drawn as
The mechanism and the product of the given reaction were determined on the basis of reversible addition of the uncharged nucleophile to the
(c)
Interpretation:
The complete and detailed mechanism of the given reaction is to be drawn and the product is to be predicted.
Concept introduction:
There are two locations in an
Answer to Problem 18.6P
The product of given reaction is
The mechanism of the reaction is
Explanation of Solution
Pyrrolidine is uncharged nucleophile and favors conjugate addition to an
After the nucleophilic addition, two proton transfer steps occur to produce an uncharged enol. The enol form is relatively unstable and rapidly tautomerizes to the more stable keto form.
Thus, the final product of the reaction is
And the complete mechanism of the reaction can be drawn as
The mechanism and the product of the given reaction were determined on the basis of reversible addition of the uncharged nucleophile to the
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Chapter 18 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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