What is Wilkinson Catalyst?
Wilkinson’s catalyst is a coordinate compound of rhodium. It enables the reaction to proceed in a faster manner. It is used in the hydrogenation reaction of the unsaturated organic compound. In this article, we have covered the IUPAC name of the Wilkinson catalyst, its uses, its structure, and its mechanism.
Wilkinson Catalyst Formula
The Wilkinson catalyst formula is [RhCl(PPh3)3]. The Wilkinson Catalyst Formula represents the coordinate compound of rhodium. Its formula is made up of one rhodium, one chloride, and three PPh3 units.
IUPAC Name of Wilkinson Catalyst
The IUPAC name of the Wilkinson catalyst is Chloridotris (triphenylphosphine) rhodium(I)].
Wilkinson's Catalyst Structure
In Wilkinson’s catalyst structure the rhodium is bonded with three triphenylphosphine units by three single covalent bonds and one chlorine element is bonded with rhodium by a single covalent bond. Wilkinson catalyst hybridisation is dsp2. The dsp2 hybridisation represents the square planar shape. It is an inner complex molecule because the orbital involved in this compound is inner 3d.
Properties of Wilkinson Catalyst
Physical Properties of Wilkinson Catalyst
The Wilkinson catalyst exists in the solid-state.
The Wilkinson catalyst is red-brown.
The Wilkinson catalyst is not soluble in polar compounds such as water and it is soluble in nonpolar compounds such as benzene, dichloromethane, and tetrahydrofuran.
The molecular mass of the Wilkinson catalyst is 925.22 grams/mole.
The melting point of the Wilkinson catalyst is around 520 K.
Chemical Properties of Wilkinson Catalyst
The chemical properties shown by the Wilkinson catalyst are the result of the electronic configuration and the shape attained by the catalyst.
The hybridisation of the Wilkinson catalyst is dsp2 and its shape is a square planner.
Wilkinson catalyst RhCl(PP3)3 reacts with the carbon monoxide and forms bis (triphenylphosphine) rhodium carbonyl chloride RhCl(CO)(PPh3)2 as a product. This formed product compound can also be formed by the reaction with the aldehydes.
RhCl(PPh3)3 + RCHO → RhCl(CO)(PPh3)2 + RH + PPh3
Wilkinson catalysts can form a dimer when mixed in the benzene solution. This formed dimer [RhCl(PPh3)3 is poorly soluble and red.
The Wilkinson catalyst can be converted into the hydridotetrakis (triphenylphosphine) rhodium (I) HRh (PPh3)4 on reacting it with the alkali, hydrogen, and excess triphenylphosphine.
RhCl(PP3)3 + H2 + base → HRh (PPh3)4
Wilkinson Catalyst Uses
The Wilkinson catalyst is widely used for the hydrogenation reaction of unsaturated hydrocarbons (olefins). It adds the molecular hydrogen at an unsaturated carbon position in the compound.
The Wilkinson catalyst can be used in the addition of a hydrogen-acyl group to the alkenes.
It plays a major role in the hydroboration reaction of the alkenes.
The Wilkinson catalyst is used in the selective hydrogenation of the alkenes. It preferably adds the hydrogen at the least hindered unsaturated carbon position.
Catalytic Hydrogenation of Alkenes
The Wilkinson catalyst is widely used in the hydrogenation process. It adds molecular hydrogen to the unsaturated carbon in the compound. It preferably adds hydrogen to the less hindered carbon.
Catalytic Hydrogenation Mechanism
The first step involved in the hydrogenation mechanism is the dissociation of the triphenylphosphine ligands, which results in the formation of a 14 or 12 electron complex.
Then it undergoes oxidative hydrogenation.
The pi complex with the alkene is formed.
Migratory insertion and reductive elimination complete the alkane formation step.
Preparation of the Wilkinson Catalyst
Wilkinson catalysts can be prepared from the hydrated form of rhodium(III) chloride. Rhodium (III) chloride undergoes the reaction with excess triphenylphosphine with ethanol. Here, ethanol acts as a refluxing agent. Triphenylphosphine is a good reducing agent and is represented as P(C6H5)3. In the preparation reaction of the Wilkinson catalyst, triphenylphosphine reacts with the rhodium chloride and reduces it from the +3 oxidation state to the +1 oxidation state.
4P(C6H5)3 + RhCl3(H2O)3 → RhCl(P(C6H5)3)3 + OP(C6H5)3 + 2HCl + 2H2O
Did You Know?
Wilkinson catalyst represents the name of chemist and Nobel laureate Sir Geoffrey Wilkinson. He first popularized its use.
The oxidation state of rhodium is +4 to -3. In the Wilkinson catalyst, the oxidation state of the rhodium is +1.
Wilkinson catalysts have the ability to reduce double bonds or alkenes. It is a red-brown colored solid. The Wilkinson catalyst is soluble in hydrocarbon solvents such as dichloromethane tetrahydrofuran and Benzene. This is a widely used compound in the halogenation of alkenes.
Formula of Wilkinson Catalyst
The formula of the Wilkinson catalyst is RhCl(PPh3)3.
The scientific name that describes its structure as well is chlorotris(triphenylphosphine)rhodium(I) in which rhodium is +1 in an Oxidation State.
Rhodium in Wilkinson's catalyst has four complexes that allow Rhodium to reduce the double bond. to form a complex.
The large size of the molecule allows it to reduce the least hindered double bond. Wilkinson's catalyst will only reduce the least hindered double bond, even when there is more than one double bond on the molecule because that is where the catalyst is able to fit.
Melting point - 518 - 523k
Molar mass - 925.22gms/mole
Soluble in - hydrocarbon solvents
It has a square planar coordination geometry.
The compound when stirred into a solution of benzene undergoes dimerization.
Yields (RhCl(CO)(PPh3)2) when it reacts with carbon monoxide.
Extensively used for halogenation of alkenes.
Selectively reduces double bonds or alkenes which makes it useful in the reduction of a specific double bond in a molecule.
The catalyst can be obtained by treating an excess of triphenylphosphine in reflecting ethanol with rhodium(|||) chloride hydrate. Triphenylphosphine oxidizes itself from the oxidation state by serving as a two-electron reducing agent.
FAQs on Wilkinson Catalyst
1. Why is the Wilkinson catalyst an organometallic compound?
It is an organometallic compound extensively used for the halogenation of alkenes which also develops Rh-C bond during its mechanism. Organometallic chemistry contains the chemistry of metal-carbon bonds. Chemical formula of Wilkinson catalyst shows that it contains carbon and also metal rhodium. So, it is a metallic organ compound.
2. How does a catalyst work?
Catalysts generally involve themselves directly as intermediaries with their substrates in the process of reaction. By the end of a reaction, the catalysts are regenerated to their original state and as a result, no net change takes place so they can again involve themselves in a new reaction. Catalysts are widely known for accelerating a chemical reaction so that an amount of product can be acquired in a limited time.
3. What are a few examples of catalysts?
Examples of Catalysts: Zinc oxide which is consumed in the reaction between Sulphur and natural rubber concentrated sulphuric acid used in the esterification of carboxylic acid and alcohol, and phosphoric acid which is used in the hydration of alkenes.
4. Why do transition metals and their compounds act as a good catalysts?
This can be explained by giving two facts:
Transition metals do give a suitable surface for reactions to occur.
Transition metals also provide a new path for the reaction with lower activation energy.
5. Where can I find concept pages of my syllabus topics?
You can find concept pages of a syllabus topic on the official website of Vedantu and can also download the app from the Play Store. The Experts on Vedantu also provide a detailed explanation as per your topics, subjects, and chapters. It also provides a number of learning aids for you to choose from, that can help in the preparation of your competitive as well as the academic exam.
6. What is Wilkinson Catalyst?
Wilkinson catalyst is the coordinate compound of the rhodium with triphenylphosphine and chloride. The hybridization possessed by the catalyst is dsp2 and the shape is a square planner.
7. Write the Properties of the Wilkinson Catalyst.
The properties of Wilkinson catalyst are:
Wilkinson catalyst is a solid compound.
It exists in the red-brown colour compound.
Wilkinson catalyst is sparingly soluble in the polar compound. These are soluble in non-polar organic compounds.
Wilkinson catalyst RhCl(PP3)3 gives a reaction with the carbon monoxide (CO) and forms bis (triphenylphosphine) rhodium carbonyl chloride RhCl(CO)(PPh3)2 as a reaction product. This compound can also be formed by the reaction with aldehydes.
RhCl(PPh3)3 + RCHO → RhCl(CO)(PPh3)2 + RH + PPh3