1. Two Rh(I)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn catalyst, are shown below. They are known to operate by different mechanisms. PF6 Ph;P., RhPPha 'PPH3 Ph2 „P Rh Ph2 Wilkinson Schrock-Osborn 5-hexene-2-one (a) For each catalyst, give the mechanism for hydrogenation of 5-hexene-2-one. Please name each elementary step (e.g. oxidative addition, migratory insertion, dissociation, etc.).

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
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1. Two Rh(I)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn
catalyst, are shown below. They are known to operate by different mechanisms.
PF6
Ph;P.,
RhPPha
'PPH3
Ph2
„P
Rh
Ph2
Wilkinson
Schrock-Osborn
5-hexene-2-one
(a) For each catalyst, give the mechanism for hydrogenation of 5-hexene-2-one. Please name each
elementary step (e.g. oxidative addition, migratory insertion, dissociation, etc.).
(b) Discuss several factors that contribute to the catalysts operating by different mechanisms.
Transcribed Image Text:1. Two Rh(I)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn catalyst, are shown below. They are known to operate by different mechanisms. PF6 Ph;P., RhPPha 'PPH3 Ph2 „P Rh Ph2 Wilkinson Schrock-Osborn 5-hexene-2-one (a) For each catalyst, give the mechanism for hydrogenation of 5-hexene-2-one. Please name each elementary step (e.g. oxidative addition, migratory insertion, dissociation, etc.). (b) Discuss several factors that contribute to the catalysts operating by different mechanisms.
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