1. Two Rh(1)-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 Ph2 Ph,P.. Rh Rh CI 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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Chapter1: Chemical Foundations
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1. Two Rh(1)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn
catalyst, are shown below. They are known to operate by different mechanisms.
Ph2
PF6
PPH3
Ph,P.,
Rh
PPH3
CI
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.
DELL
Transcribed Image Text:1. Two Rh(1)-phosphine catalysts for olefin hydrogenation, Wilkinson's catalyst and a Schrock-Osborn catalyst, are shown below. They are known to operate by different mechanisms. Ph2 PF6 PPH3 Ph,P., Rh PPH3 CI 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. DELL
2. Predict the major product of each reaction. Make sure to indicate the relative stereochemistry at each
site of hydrogenation, if applicable.
D2
RHCI(PPh,)3 cat.
(a)
(b)
H2
[(COD)Ir(PCY3)(py)][PF6] cat.
(c)
H2
RHCI(PPH3), cat.
"OBz
(d)
OH O
H2
[Rh(NBD)(dppb)[PFJ cat.
N.
***
****
Transcribed Image Text:2. Predict the major product of each reaction. Make sure to indicate the relative stereochemistry at each site of hydrogenation, if applicable. D2 RHCI(PPh,)3 cat. (a) (b) H2 [(COD)Ir(PCY3)(py)][PF6] cat. (c) H2 RHCI(PPH3), cat. "OBz (d) OH O H2 [Rh(NBD)(dppb)[PFJ cat. N. *** ****
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