The Curiously Intertwined Histories of Benzene and Cyclohexane

E. W. Warnhoff
University of Western Ontario, London, Canada N6A 5B7
J. Chem. Educ., 1996, 73 (6), p 494
DOI: 10.1021/ed073p494
Publication Date (Web): June 1, 1996
History, Education, and Documentation

Abstract

The first reduction of benzene, which was done by means of hydrogen iodide in the middle of the 19th century, led to a saturated hydrocarbon initially thought to be hexane and later to be hexahydrobenzene (cyclohexane). However, when the synthesis of cyclohexane was accomplished in 1894, it was found to be different from the so-called hexahydrobenzene. Further work revealed that the hexahydrobenzene from the HI reaction was actually methylcyclopentane, the product of rearrangement.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

History / Philosophy

Keywords (Subject):

Alkanes / Cycloalkanes
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  • Received: August 03, 2009

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