An Engaging Illustration of the Physical Differences among Menthol Stereoisomers

Autor:	Edward M. Treadwell, T. Howard Black
Rok vydání:	2005
Předmět:	chemistry.chemical_compound Chemistry Melting point Diastereomer Organic chemistry General Chemistry Enantiomer Menthol Melting-point depression Education
Zdroj:	Journal of Chemical Education. 82:1046
ISSN:	1938-1328 0021-9584
DOI:	10.1021/ed082p1046
Popis:	The differences and similarities in the physical behavior of enantiomers and diastereomers can easily be demonstrated using the commercial stereoisomers (?)-menthol, (+)-menthol, (+)-isomenthol, and (+)-neomenthol. Thin-layer chromatography and melting point determinations clearly show that diastereomers have different physical properties from enantiomers and each other, but that enantiomers have identical physical properties in achiral environments. By obtaining a mixed melting point and optical rotations the difference in enantiomers can be observed. The exercise serves to reinforce the consequences of stereochemistry in terms of physical properties, as well as relating the differences in structure that lead to different types of stereoisomers. An attention-getting demonstration, suitable for the classroom or laboratory, of the melting point depression of a mixture of two enantiomers is also featured.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dc0a1944fc2cce85f2de29b6492fce44 https://doi.org/10.1021/ed082p1046 Zobrazit plný text záznamu