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On the Disproportionations of Cyclohexene and Related Compounds

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Alex Bunjes , Ingo Eilks , Manfred Pahlke and Bernd Ralle

Universität Dormund, FB Chemie, Didaktik der Chemie 1, Otto-Han-Strasse 6, 44227, Dortmund, Germany

J. Chem. Educ., 1997, 74 (11), p 1323

DOI: 10.1021/ed074p1323

Publication Date (Web): November 1, 1997

Section:

History, Education, and Documentation

Abstract

The catalytic hydrogenation of liquid hydrocarbons is easy to realize in a simple laboratory experiment using a palladium catalyst. In the case of hydrogenation cyclohexen or cyclohexadiene in addition to the expected finding of cyclohexane among the hydrogenation products, the formation of benzene can be observed. In absence of hydrogen, the disproportionation of both starting materials to cyclohexane and benzene takes place. In chemical education these experiments can be used for an experimental introduction of the benzene molecule. They also give the rare opportunity to discuss processes happening on the surface of a catalyst during catalysis. A two-step-mechanism is worked out with the pupils as a hypothesis which than is successfully checked by an experiment and the analysis by GC.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alkanes / Cycloalkanes

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Hydrogenation of Arenes over Silica-Supported Catalysts That Combine a Grafted Rhodium Complex and Palladium Nanoparticles: Evidence for Substrate Activation on Rh_s_ingle_-_s_ite−Pd_m_etal Moieties
Pierluigi Barbaro, Claudio Bianchini, Vladimiro Dal Santo, Andrea Meli, Simonetta Moneti, Rinaldo Psaro, Adriana Scaffidi, Laura Sordelli, and Francesco Vizza
Journal of the American Chemical Society2006 128 (21), 7065-7076
- Hydrogenation of Arenes over Silica-Supported Catalysts That Combine a Grafted Rhodium Complex and Palladium Nanoparticles: Evidence for Substrate Activation on Rh_s_ingle_-_s_ite−Pd_m_etal Moieties
  Pierluigi Barbaro, Claudio Bianchini, Vladimiro Dal Santo, Andrea Meli, Simonetta Moneti, Rinaldo Psaro, Adriana Scaffidi, Laura Sordelli, and Francesco Vizza
  Journal of the American Chemical Society2006 128 (21), 7065-7076
  The complex Rh(cod)(sulfos) (RhI; sulfos = -O3S(C6H4)CH2C(CH2PPh2)3; cod = cycloocta-1,5-diene), either free or supported on silica, does not catalyze the hydrogenation of benzene in either homogeneous or heterogeneous phase. However, when silica contains ...
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Received: August 03, 2009

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On the Disproportionations of Cyclohexene and Related Compounds