Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 25.17, Problem 28P
Propose mechanisms for the Claisen condensation and aldol addition that comprise the first two steps of the biosynthesis of isopentenyl pyrophosphate.
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Propose the synthesis for the following transformations.
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The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of
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hydrolysis of the enamine in dilute acid to regenerate the ketone.
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Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine.
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Chapter 25 Solutions
Organic Chemistry
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- Propose mechanisms for the Claisen condensation and aldol addition that comprise the first two steps of the biosynthesis of isopentenyl pyrophosphate.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forwardPredict the products of aldol condensation, followed by dehydration, of the followingketones and aldehydes. c) cyclohexanonearrow_forward
- Under normal mild conditions, ketones are quite resistant to oxidation. But when treated with peracids (such as peracitic acid), they undergo an oxidation reaction. Explain how this happens using the following reaction showing a mechanism for the reaction. Cyclopentanone + peracetic acidarrow_forwardAn α, β-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation–oxidation reaction. A selenoxide is formed as anintermediate. Propose a mechanism for the reaction.arrow_forwardComplete the following transformations by providing reagents or products:arrow_forward
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