Multistep Synthesis of a Terphenyl Derivative Showcasing the Diels–Alder Reaction
An adaptable multistep synthesis project designed for the culmination of a second-year organic chemistry laboratory course is described. The target compound is a terphenyl derivative that is an intermediate in the synthesis of compounds used in organic light-emitting devices. Students react a conjug...
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| Veröffentlicht in: | Journal of chemical education 2015-07, Vol.92 (7), p.1209-1213 |
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| container_title | Journal of chemical education |
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| creator | Davie, Elizabeth A. Colby |
| description | An adaptable multistep synthesis project designed for the culmination of a second-year organic chemistry laboratory course is described. The target compound is a terphenyl derivative that is an intermediate in the synthesis of compounds used in organic light-emitting devices. Students react a conjugated diene with dimethylacetylene dicarboxylate in a Diels–Alder reaction, then use enolate chemistry to isomerize and aromatize the adduct. Analysis of the synthesized intermediates and final compound is accomplished by thin-layer chromatography, NMR, and melting point. The synthesis can be expanded to four or five steps by linking to a previously published preparation of the diene. In addition to gaining experience with classic reactions in undergraduate organic chemistry courses, students are exposed to the utility of NMR spectroscopy by tracking subtle changes in the NMR spectra of structurally similar species. |
| doi_str_mv | 10.1021/acs.jchemed.5b00318 |
| format | Article |
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Colby</creatorcontrib><collection>ERIC</collection><collection>ERIC (Ovid)</collection><collection>ERIC</collection><collection>ERIC</collection><collection>ERIC (Legacy Platform)</collection><collection>ERIC( SilverPlatter )</collection><collection>ERIC</collection><collection>ERIC PlusText (Legacy Platform)</collection><collection>Education Resources Information Center (ERIC)</collection><collection>ERIC</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Journal of chemical education</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Davie, Elizabeth A. Colby</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><ericid>EJ1068990</ericid><atitle>Multistep Synthesis of a Terphenyl Derivative Showcasing the Diels–Alder Reaction</atitle><jtitle>Journal of chemical education</jtitle><addtitle>J. Chem. Educ</addtitle><date>2015-07-14</date><risdate>2015</risdate><volume>92</volume><issue>7</issue><spage>1209</spage><epage>1213</epage><pages>1209-1213</pages><issn>0021-9584</issn><eissn>1938-1328</eissn><coden>JCEDA8</coden><abstract>An adaptable multistep synthesis project designed for the culmination of a second-year organic chemistry laboratory course is described. The target compound is a terphenyl derivative that is an intermediate in the synthesis of compounds used in organic light-emitting devices. Students react a conjugated diene with dimethylacetylene dicarboxylate in a Diels–Alder reaction, then use enolate chemistry to isomerize and aromatize the adduct. Analysis of the synthesized intermediates and final compound is accomplished by thin-layer chromatography, NMR, and melting point. The synthesis can be expanded to four or five steps by linking to a previously published preparation of the diene. 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| identifier | ISSN: 0021-9584 |
| ispartof | Journal of chemical education, 2015-07, Vol.92 (7), p.1209-1213 |
| issn | 0021-9584 1938-1328 |
| language | eng |
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| source | ACS Publications |
| subjects | Chemical reactions Chemical synthesis Chemistry College students Devices Diels-Alder reactions Instructional design Laboratory Experiments Light emission Melting point Melting points NMR NMR spectroscopy Nuclear magnetic resonance Organic Chemistry Science education Science Experiments Science Instruction Science Laboratories Scientific Concepts Spectroscopy Spectrum analysis Students Thin layer chromatography Undergraduate Study |
| title | Multistep Synthesis of a Terphenyl Derivative Showcasing the Diels–Alder Reaction |
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