(a)
Interpretation:
The complete, detailed mechanism for the given reaction is to be drawn. The major product is to be predicted.
Concept introduction:
Phosphorus tribromide (
Answer to Problem 17.67P
The complete, detailed mechanism and the major product for the given reaction is drawn as shown below:
Explanation of Solution
The given starting material and reagents are as shown below:
The reagent used for the first step of this reaction is Phosphorus tribromide (
The above formed alkyl bromide further undergoes an
The above Wittig reagent undergoes Wittig reaction with acetone. In a Wittig reaction, the
The overall mechanism and the major product of the given reaction is as shown below:
The product of the given reaction and complete mechanism is drawn on the basis of the given reagents.
(b)
Interpretation:
The complete, detailed mechanism for the given reaction is to be drawn. The major product is to be predicted.
Concept introduction:
The
Answer to Problem 17.67P
The complete, detailed mechanism and the major product for the given reaction is drawn as shown below:
Explanation of Solution
The given starting material and reagents are as shown below:
In the first reaction, a new C-C bond is formed and a phenyl group is added to the carbonyl carbon. Grignard reagents can react rapidly with
Further, this alcohol undergoes deprotonation by NaH to form negatively charged alkoxide. This alkoxide acts as a strong nucleophile and attacks ethyl bromide via
The overall mechanism and the major product of the given reaction are as shown below:
The product of the given reaction and complete mechanism is drawn on the basis of the mechanism for Grignard reagent and Williamson ether synthesis.
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Chapter 17 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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