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Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry Experiment

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Carlos F. Marcos

Departamento de Química Orgánica, Facultad de Veterinaria, Universidad deExtremadura, Avenida de la Universidad s/n, E-10071 Caceres, Spain

Ricardo Bossio , Stefano Marcaccini and Roberto Pepino

CNR, Dipartimento di Chimica Organica Ugo Schiff, Univerità di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

J. Chem. Educ., 2000, 77 (3), p 382

DOI: 10.1021/ed077p382

Publication Date (Web): March 1, 2000

Abstract

We present two experiments for the synthesis of, respectively, a ß-lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group. Analysis of the reaction mechanisms exemplifies the importance of electronics in the pathway the reaction takes and, therefore, in the nature of the products.

All the reactions involved are high yielding and easy to carry out, and the products can be directly isolated with a good degree of purity with no need of further manipulation.¹H NMR and IR spectra show characteristic signals of the products, and their study constitutes an interesting problem of structural elucidation.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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