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Although the following compound is a substituted acetone

Chapter 16, Problem 51P

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QUESTION:

(a) Although the following compound is a substituted acetone derivative, it cannot be made by the acetoacetic ester synthesis. Explain why (two reasons).

                                     

(b) The use of LDA to make enolate ions (Sections 22-2B and 22-3) has provided alterna-

tives to the acetoacetic ester synthesis. Show how you might make the compound shown

in part (a), beginning with 1,3-diphenylacetone.

(c) Enamine reactions (Section 22-4) occur under relatively mild conditions, and they often

give excellent yields of compounds like the one shown in part (a). Show how you might

use an enamine reaction for this synthesis, beginning with 1,3-diphenylacetone.

Questions & Answers

QUESTION:

(a) Although the following compound is a substituted acetone derivative, it cannot be made by the acetoacetic ester synthesis. Explain why (two reasons).

                                     

(b) The use of LDA to make enolate ions (Sections 22-2B and 22-3) has provided alterna-

tives to the acetoacetic ester synthesis. Show how you might make the compound shown

in part (a), beginning with 1,3-diphenylacetone.

(c) Enamine reactions (Section 22-4) occur under relatively mild conditions, and they often

give excellent yields of compounds like the one shown in part (a). Show how you might

use an enamine reaction for this synthesis, beginning with 1,3-diphenylacetone.

ANSWER:

Solution 51P

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