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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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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Consider the Stork reaction between acetophenone and 3-buten-2-one.
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Draw the structure of the final product.
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The following molecule can undergo keto–enol tautomerization upon addition of hydroxide. Draw the structure of the enol form and the mechanism by which it forms.
Chapter 25 Solutions
Organic Chemistry
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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 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_forwardPropose mechanisms for the Claisen condensation and aldol addition that comprise the first two steps of the biosynthesis of isopentenyl pyrophosphate.arrow_forwardUnder 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_forward
- Predict the products of aldol condensation, followed by dehydration, of the followingketones and aldehydes. c) cyclohexanonearrow_forwardComplete the following transformations by providing reagents or products:arrow_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_forward
- Propose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forward2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)arrow_forwardGive the product of the following transformation:arrow_forward
- 2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis. Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)arrow_forwardThe reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.arrow_forwardProvide a chemical reaction on how the following compounds can be synthesized via aldol condensation. note that the starting reactants should be benzaldehyde and a ketonearrow_forward
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