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ERIC Number: EJ1173142
Record Type: Journal
Publication Date: 2018-Mar
Pages: 7
Abstractor: As Provided
ISSN: ISSN-0021-9584
Exploiting Carvone to Demonstrate Both Stereocontrol and Regiocontrol: 1,2- vs 1,4-Addition of Grignard Reagents and Organocuprates
Truong, Thai Phat; Bailey, Sophia J.; Golliher, Alexandra E.; Monroy, Erika Y.; Shrestha, Uttar K.; Maio, William A.
Journal of Chemical Education, v95 n3 p438-444 Mar 2018
The ability of certain organometallic reagents to react via 1,2- or 1,4-addition to an a,ß-unsaturated ketone is a fundamental example of regioselectivity at the second-year undergraduate organic level. The following two experiments were designed to demonstrate this preference by exploiting carvone as an inexpensive chiral, nonracemic substrate. The first, intended for a typical undergraduate audience, makes use of phenylmagnesium bromide; the second calls for the manufacture of lithium dimethylcuprate from a stock solution of methyl lithium and copper(I) iodide and is envisioned to be carried out by upper-division students. Importantly, due to the chiral nature of carvone, these addition reactions are highly stereoselective and will provide an opportunity for students to revisit stereochemistry. Also discussed are several thoughts on assessment of student learning as well as an easy to adopt protocol that details reaction setup, aqueous workup, purification, waste management, and the analysis of products using [superscript 1]H NMR spectroscopy.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: National Science Foundation (NSF)
Authoring Institution: N/A
Identifiers - Location: New Mexico
Grant or Contract Numbers: 1452489