
(a)
Interpretation:
The structures of the
Concept introduction:
The Wilkinson’s Catalyst is a common name of coordination compound

Answer to Problem 18.15P
The structures of the transition-metal complexes involved in each of the given mechanistic step are shown below.
1. The oxidative addition reaction is shown below.
2. The ligand substitution of one
3. 1, 2-insertion of alkene into a
4. Reductive elimination of the
Explanation of Solution
The general formula for the calculation of electron count in a given formula is shown below.
The number of valence electrons present in rhodium is
1. In oxidative addition reaction, the central metal atom gets oxidized with the addition of two ligands and there is an increase in electron count at the central metal atom.
The oxidative addition reaction is shown below.
Figure 1
The electron count in
The electron count in
2. The ligand substitution reaction of one
Figure 2
The electron count in
The electron count in
3. 1, 2-insertion of alkene into a
Figure 3
The electron count in
The electron count in
The electron count in
4. Reductive elimination of the alkane product to generate the catalyst is shown below.
Figure 4
The electron count in
The electron count in
The catalytic hydrogenation of alkene by wilkinson’s catalyst and electron count is shown in Figure 1, 2, 3 and 4.
(b)
Interpretation:
The stereochemistry of the product if
Concept introduction:
The complex that follows

Answer to Problem 18.15P
The reaction between cis-alkene with the deuterium substituted wilkinson’s catalyst is shown below.
This shows syn-addition of deuterium on alkene.
Explanation of Solution
Reduction of cis-alkene with the deuterium substituted Wilkinson’s catalyst.
Figure 5
In the reduction of cis-alkene with the deuterium substituted Wilkinson’s catalyst. Hydrogen added on Wilkinson’s catalyst for hydrogenation of alkene is replaced by deuterium. The alkene is present in the plane of the paper, the deuterium can attack the alkene either from below the plane or above the plane.
Therefore, this shows that syn-addition of deuterium also takes place.
The reaction in Figure 5 shows that syn addition of hydrogen takes place even when it is substituted by deuterium.
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Chapter 18 Solutions
Organic Chemistry
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
