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Although the following compound is a substituted acetone

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 51P Chapter 22

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 51P

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 alternatives 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.

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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Although the following compound is a substituted acetone