Figure 23.4 - Mechanism of the Claisen Condensation Reaction. 3 The tetrahedral intermediate expels ethoxide ion to yield a new carbonyl compound, ethyl acetoacetate. 4 But ethoxide ion is a strong enough base to deprotonate ethyl acetoacetate, shift- ing the equilibrium and driving the overall reaction to completion. 5 Protonation of the enolate ion by addition of aqueous acid in a separate step yields the final 3-keto ester product. H3C H3C 17 H3C O=U O=C HH 4 1:CIH O=C Η Η OEt OEt 5 H30+ OEt + EtO™ + EtOH

Figure 23.4 - Mechanism of the Claisen Condensation Reaction. 3 The tetrahedral intermediate expels ethoxide ion to yield a new carbonyl compound, ethyl acetoacetate. 4 But ethoxide ion is a strong enough base to deprotonate ethyl acetoacetate, shift- ing the equilibrium and driving the overall reaction to completion. 5 Protonation of the enolate ion by addition of aqueous acid in a separate step yields the final 3-keto ester product. H3C H3C 17 H3C O=U O=C HH 4 1:CIH O=C Η Η OEt OEt 5 H30+ OEt + EtO™ + EtOH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 81AP

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Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occurs by initial protonation of the nitrogen atom, followed by nucleophilic addition of water. Review the mechanism of base-catalyzed nitrile hydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzed reaction, using curved arrows to represent electron flow in each step.
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich WĂ¶hler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
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Please help with question 38
Complete the reaction and write the products
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The question is attached below
13
Provide a synthetic route for the following compound using the indicated starting material