In the previous section, we learned how to use malonic ester as a starting material in the

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In the previous section, we learned how to use malonic ester as a starting material in the preparation of substituted carboxylic acids (the malonic ester synthesis). That method employed a step in which the enolate of malonic ester attacked an alkyl halide to give an alkylation product. In this section, we saw that the enolate of malonic ester can attack many electrophilic reagents other than simple alkyl halides. Specifically, the enolate of malonic ester can attack any of the Michael acceptors in the following table. Using malonic ester as your starting material and any other reagents of your choice, show how you would prepare each of the following compounds.

MICHAEL DONORS MICHAEL ACCEPTORS EtO &+ OEt `H &+ CEN OEt OEt `NH2 R. NO2 R2CuLi &+ CEN NO2

(a)

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(b)

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Organic Chemistry

ISBN: 978-0470917800

1st edition

Authors: David R. Klein

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