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In the Laboratory
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Reactivity of the Monoterpenoid Nerol with p-Toluenesulfonic and Chlorosulfonic Acids: Selective Syntheses of α-Terpineol and α-Cyclogeraniol. An Activity for the Undergraduate Organic Lab
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Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez
Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
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July 2006
Vol. 83 No. 7
p. 1052
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| Abstract |
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The selective syntheses of the cyclic monoterpenoids α-terpineol or α-cyclogeraniol from the acyclic monoterpenoid nerol using p-toluenesulfonic acid or chlorosulfonic acid as cyclizing agents, respectively, are described. The different behavior of nerol under diverse experimental conditions such as nature of the acid agents, solvents, and reaction temperatures is analyzed. The didactic usefulness of these experiments has been rationalized.
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| Supplement |
The full description of these experiments with materials and reagents required, detailed experimental procedures, spectra and assignments, further explanations on biomimetic cyclizations and carbocation chemistry, more experimental tasks to supplement the described procedures, notes and tips for the instructor and questions for students, among other helpful material, are available.
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JCE2006p1052W.doc (Microsoft Word)
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| More Information |
Citation |
Linares-Palomino, Pablo J.; Salido, Sofía; Altarejos, Joaquín; Nogueras, Manuel; Sánchez, Adolfo. J. Chem. Educ. 2006 83 1052.
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Keywords |
Alcohols; Alkenes; Carbocations; Gas Chromatography; Hands-On Learning / Manipulatives; Laboratory Instruction; Mechanisms of Reactions; Microscale Lab; Natural Products; Organic Chemistry; Synthesis; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
5/26/2006
5/31/2006
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