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Reaction of Dibenzoylethylene with Hydriodic Acid

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Fred H. Greenberg

Department of Chemistry, SUNY College at Buffalo, Buffalo, NY 14222

J. Chem. Educ., 2000, 77 (4), p 505

DOI: 10.1021/ed077p505

Publication Date (Web): April 1, 2000

Section:

History, Education, and Documentation

Abstract

An experiment for the sophomore organic course is described in which dibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Advantages are a short reaction time, 1-2 min, and a nearly quantitative yield before purification. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Microscale Lab

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown Substance
Timothy D. Shine and Neil M. Glagovich
Journal of Chemical Education2005 82 (9), 1382
- Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown Substance
  Timothy D. Shine and Neil M. Glagovich
  Journal of Chemical Education2005 82 (9), 1382
  An undergraduate organic laboratory designed to teach the use of IR and NMR spectra interpretation in the identification of an unknown substance has been developed. This laboratory requires the student to obtain the IR spectrum of an unknown substance and,...
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