Steam distillation of essential oils - Carvone from caraway

Garin, David L.

doi:10.1021/ed053p105

Cited by 9 publications

(8 citation statements)

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“…Shortly after the publication of their work, Steven Murov and Miles Pickering (Murov and Pickering 1973) suggested that experiments using carvone could be of value in education, specifically in organic chemistry laboratories. The experiment has since become widely used and frequently cited (Garin 1976;Davis et al 2003;Kraft and Mannschreck 2010;O'Shea, Von Riesen, and Rossi 2012).…”

Section: The Nature Of Chirality (Chemistry)mentioning

confidence: 99%

“…These are often compared to the same tests performed for enantiomerically pure samples of (R)-(-)-Carvone and (S)-(+)-Carvone. Students are typically asked to notice, through comparison with a student who distilled the other enantiomer (or through comparison with their own results if they distilled both enantiomers), that there is no difference in mixed melting point, NMR, and infrared spectrometry for both of their distillates (barring the inevitable impurities which will typically remain) (Garin 1976). Thus, the standard presentation of the Carvone ELE includes a final step in which students measure the angle of rotation of polarized light through the use of a polarimeter.…”

Section: The Nature Of Chirality (Chemistry)mentioning

confidence: 99%

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Representing in the Student Laboratory

Boesch

2018

Transversal

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In this essay, I will expand the philosophical discussion about the representational practice in science to examine its role in science education through four case studies. The cases are of what I call ‘educational laboratory experiments’ (ELEs), performative models used representationally by students to come to a better understanding of theoretical knowledge of a scientific discipline. The studies help to demonstrate some idiosyncratic features of representational practices in science education, most importantly a lack of novelty and discovery built into the ELEs as their methodology is solidified when it becomes a widely spread educational tool within a discipline. There is thus an irreducible role for the historical development of ELEs in understanding their representational nature and use. The important role of the historical development of ELEs leads to an interesting way that educators can use ELEs as a means of connecting students to important historical developments within their disciplines.

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Section: The Nature Of Chirality (Chemistry)mentioning

confidence: 99%

Section: The Nature Of Chirality (Chemistry)mentioning

confidence: 99%

Representing in the Student Laboratory

Boesch

2018

Transversal

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“…S (+)-Carvone from caraway oil and R (−)-carvone from spearmint oil have been isolated using preparative gas chromatography, steam-distillation of caraway seeds, liquid chromatography, column chromatography, and vacuum distillation. − In this experiment, vacuum distillation is used to remove the major impurity R (+)-limonene (Figure ). Techniques are presented to eliminate the foaming problems reported by Murov et al The purities of the distillates were checked by gas chromatography and infrared spectrometry.…”

Section: Introductionmentioning

confidence: 99%

Combination of X-ray Diffraction and Specific Rotation to Unequivocally Characterize Carvone Semicarbazone Derivatives

Dolhun

Müller

2020

J. Chem. Educ.

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Single-crystal X-ray structures, melting points, and students’ specific rotation results on carvone semicarbazone derivatives are presented with experimental details. Critical parameters are identified to ensure the success of the experiment. Procedures developed here were tested in a laboratory course, consisting of approximately 70 students over three semesters. This experiment teaches undergraduate students important new instrumental methodology for characterizing a sample, allowing students to gain skills from hands-on experience using modern analytical instrumentation, and analyzing data to achieve a conclusion.

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“…Essential oils are an easily accessible class of such compounds. However, relatively few experiments involving these interesting molecules have appeared in this Journal (1)(2)(3)(4)(5)(6)(7)(8)(9)(10). Even fewer experiments have utilized NMR spectrometry to determine the structures of these compounds and their derivatives (3,(11)(12)(13)(14)(15).…”

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confidence: 99%