In 1887, the Russian chemist Sergei Reformatsky at the University of Kiev dis-covered that treatment of an a-haloester with zinc metal in the presence of analdehyde or a ketone followed by hydrolysis in aqueous acid results in formation ofa B-hydroxyester. This reaction is similar to a Grignard reaction in that a key inter-mediate is an organometallic compound, in this case, a zinc salt of an ester enolate anion.Grignard reagents, however, are so reactive that they undergo self-condensationwith the ester.O [ZnBr]+ОНZn1. PHCHOBRCH,COE.CH=COELPHCHCH,COEtbenzene2. Н,О, НСZinc salt of anenolate anionA B-hydroxyester(rácemic)Show how a Reformatsky reaction can be used to synthesize these compounds from analdehyde or a ketone and an a-haloester. ОН(four stereoisomers:two racemic mixtures)as

The given reaction is represented as follows:

Answered: In 1887, the Russian chemist Sergei…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.37P

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The mechanism of the Fischer esterification was controversial until 1938, when IrvingRoberts and Harold Urey of Columbia University used isotopic labeling to follow thealcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was addedto a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,and the components of the mixture were separated.H2SO4OCH3 C O H CH3 O H CH3 C O CH3 H2OO18 + +(a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it is found inthe products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determinethe amounts of 18O in the separated components of the mixture
Compound A was prepared by sequential Suzuki cross-coupling reactions.First, compound 1 was treated with an aryl iodide to give compound 2, which was then treated with an aryl boronic acid to produce compound A. How wood the structures for the aryl iodide, boronic acid, and compound 2 look like.
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Given this retrosynthetic analysis, propose a synthesis for labetalol from salicylic acid and benzyl chloride. [Note: The conversion of salicylic acid to (E) involves a Friedel-Crafts acylation in which the phenolic -OH must be protected by treatment with acetic anhydride to prevent the acylation of the -OH group. The protecting group is later removed by treatment with KOH followed by acidification.]
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