As mentioned on page \(1047,\) transition metal organometallic compounds have
found use as catalysts. One example is Wilkinson's catalyst, a rhodium
compound \(\left[\mathrm{RhCl}\left(\mathrm{PR}_{3}\right)_{3}\right]\) used in
the hydrogenation of alkenes. The steps involved in the catalytic process are
outlined below. Indicate whether the rhodium compounds in each step have 18 -
or 16 -valence electrons. (See Study Question \(34 .)\)
Step \(1 .\) Addition of \(\mathrm{H}_{2}\) to the rhodium center of Wilkinson's
catalyst. (For electron-counting purposes \(\mathrm{H}\) is considered a hydride
ion, \(\left.\mathrm{H}^{-}, \text {a two-electron donor. }\right)\)
Step \(2 .\) Loss of a PR \(_{3}\) ligand (a two-electron donor) to open a
coordination site. (PR \(_{3}\) is a phosphine such as
\(\mathrm{P}\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3},\)
triphenylphosphine.)
Step \(3 .\) Addition of the alkene to the open site.
Step 4. Rearrangement to add H to the double bond. (Here the \(-\mathrm{CH}_{2}
\mathrm{CH}_{3}\) group is a two-electron donor and can be thought of as a
\(\left[\mathrm{CH}_{2} \mathrm{CH}_{3}\right]^{-}\) anion for electron counting
purposes.)
Step \(5 .\) Loss of the alkane.
Step \(6 .\) Regeneration of the catalyst.
$$\text { Net reaction: } \mathrm{CH}_{2}=\mathrm{CH}_{2}+\mathrm{H}_{2}
\longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{3}$$