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 an aldehyde or a ketone followed by hydrolysis in aqueous acid results in formation of a 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-condensation with the ester. O [ZnBr]+ ОН Zn 1. PHCHO BRCH,COE. CH=COEL PHCHCH,COEt benzene 2. Н,О, НС Zinc salt of an enolate anion A B-hydroxyester (rácemic) Show how a Reformatsky reaction can be used to synthesize these compounds from an aldehyde or a ketone and an a-haloester. НО OEt (racemic)

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 an aldehyde or a ketone followed by hydrolysis in aqueous acid results in formation of a 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-condensation with the ester. O [ZnBr]+ ОН Zn 1. PHCHO BRCH,COE. CH=COEL PHCHCH,COEt benzene 2. Н,О, НС Zinc salt of an enolate anion A B-hydroxyester (rácemic) Show how a Reformatsky reaction can be used to synthesize these compounds from an aldehyde or a ketone and an a-haloester. НО OEt (racemic)

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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