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ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > UMM chemwiki project > Alkenes and alkynes > Hydrogenation of Alkenes

Hydrogenation of Alkenes

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Addition of hydrogen to a carbon-carbon double bond is called hydrogenation. The overall effect of such an addition is the reductive removal of the double bond functional group. Regioselectivity is not an issue, since the same group (a hydrogen atom) is bonded to each of the double bond carbons. The simplest source of two hydrogen atoms is molecular hydrogen (H2), but mixing alkenes with hydrogen does not result in any discernible reaction. Although the overall hydrogenation reaction is exothermic, a high activation energy prevents it from taking place under normal conditions. This restriction may be circumvented by the use of a catalyst, as shown in the following diagram.

Recall that catalysts are substances that changes the rate (velocity) of a chemical reaction without being consumed or appearing as part of the product. Catalysts act by lowering the activation energy of reactions, but they do not change the relative potential energy of the reactants and products. Finely divided metals, such as platinum, palladium and nickel, are among the most widely used hydrogenation catalysts. Catalytic hydrogenation takes place in at least two stages, as depicted in the diagram. First, the alkene must be adsorbed on the surface of the catalyst along with some of the hydrogen. Next, two hydrogens shift from the metal surface to the carbons of the double bond, and the resulting saturated hydrocarbon, which is more weakly adsorbed, leaves the catalyst surface. The exact nature and timing of the last events is not well understood.

As shown in the energy diagram part of the figure above, the hydrogenation of alkenes is exothermic, and heat is released corresponding to the ΔE (colored green) in the diagram.

 

Because catalytic hydrogenation takes place on a planar surface, addition of hydrogen occurs on the same face of the double bond - a syn addition, in other words.  The catalytic hydrogenation of 1,2-dimethylcyclopentane will yield, for example, the cis dimethylcycloalkane product, with little or no formation of a trans product.

 

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Last Modified
09:31, 28 Feb 2014

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