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Question

What is the most suitable catalyst for reducing vinyl cyanide (CH=CHCN) to propanenitrile?

A
H2/Ni
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B
H2/Pt
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C
(Ph3P)3RhCl (Wilkinson's catalyst)
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D
LiAlH4
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Solution

The correct option is C (Ph3P)3RhCl (Wilkinson's catalyst)
Wilkinson's catalyst catalyzes the hydrogenation of alkenes.
The mechanism of this reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14 or 12electron complexes, respectively, followed by oxidative addition of H2 to the metal. Subsequent π-complexation of an alkene, intramolecular hydride transfer (olefin insertion), and reductive elimination results in extrusion of the alkane product.
Here vinyl cyanide undergoes hydrogenation to form propanenitrile using Wilkinson' catalyst.

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