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.

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.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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A1
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Which reaction sequence would be best for preparing 3,5-dibromoaniline from nitrobenzene? a. (i) excess Br2 + FeBr3 / heat (ii) 3 H₂ / Pt or Ni catalyst b. (i) H2SO4/heat (ii) excess Br2 + FeBr3 / heat (iii) 3 H₂/ Pt or Ni catalyst c. (i) 3 H₂/ Pt or Ni catalyst (ii) H2S04/heat (iii) excess HBr d. (i) 3 H2/Pt or Ni catalyst (ii) 2 Br2 in ether
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Previously (p. 1120) we mentioned that the formylation of benzene (i.e., the replacement of H by Hc=0) cannot be carried out through a standard Friedel-Crafts acylation because methanoyl chloride (formyl chloride) cannot be added directly. The Gattermann-Koch synthesis circumvents this problem by making methanoyl chloride in situ (shown at the right), using a gaseous mixture of carbon monoxide and hydrochloric acid at high pressures. With this in mind, draw the detailed mechanism for the Formyl chloride is unstable, so it is produced only temporarily. Colg) HCIG) + H CI Formyl chloride + HCIG) electrophilic aromatic substitution that takes place in the following reaction. + COg) AICI3