14-1 Reactions Involving Gain or Loss of Ligands Reactions Involving Modification of Ligands
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1 Organometallic Reaction and Catalysis 14-1 Reactions Involving Gain or Loss of Ligands 14-2 Reactions Involving Modification of Ligands 14-3 Organometallic Catalysts 14-4 Heterogeneous Catalysts Inorganic Chemistry Third Ed. Gary L. Miessler, Donald A. Tarr, 2004, Pearson Prentice Ha
2 Chapter 14 Organometallic Reaction and Catalysis Organometallic reactions Loss or gain of ligands Molecular rearrangement Formation or breaking of metal-metal bonds Reactions at the ligands themselves
3 14-1 Reactions Involving Gain or Loss of Ligands Addition or dissociation vs oxidative addition or reductive elimination
4 14-1 Reactions Involving Gain or Loss of Ligands ; ligand dissociation and substitution CO dissociation Independent of the concentration of L???
5 14-1 Reactions Involving Gain or Loss of Ligands ; ligand dissociation and substitution CO dissociation Two pathways
6 14-1 Reactions Involving Gain or Loss of Ligands ; ligand dissociation and substitution Dissociation of phosphine Dissociation The strength of M-L bonding The degree of crowding of ligand around metal
7 14-1 Reactions Involving Gain or Loss of Ligands ; ligand dissociation and substitution
8 14-1 Reactions Involving Gain or Loss of Ligands ; oxidative addition An increase in both the formal oxidation state and the coordination #
9 14-1 Reactions Involving Gain or Loss of Ligands ; oxidative addition OA cyclometallations orthometallation
10 14-1 Reactions Involving Gain or Loss of Ligands ; reductive elimination A decrease in both the formal oxidation state and the coordination # Useful organic compounds The rates of RE reactions are also affected by ligand bulk
11 14-1 Reactions Involving Gain or Loss of Ligands ; nucleophilic displacement Nucleophilic anionic organometallic complexes Collman s reagent Acyl complex ester
12 14-2 Reactions Involving Modification of Ligands ; insertion 1,1 insertion 1,2 insertion
13 14-2 Reactions Involving Modification of Ligands ; carbonyl insertion (alkyl migration) 3 plausible mechanisms
14 3 plausible mechanisms 14-2 Reactions Involving Modification of Ligands ; carbonyl insertion (alkyl migration)
15 14-2 Reactions Involving Modification of Ligands ; carbonyl insertion (alkyl migration)
16 14-2 Reactions Involving Modification of Ligands ; carbonyl insertion (alkyl migration)
17 14-2 Reactions Involving Modification of Ligands ; 1,2 insertions Alkenes into M-R bonds polymerization
18 14-2 Reactions Involving Modification of Ligands ; hydride elimination The transfer of a hydrogen atom from a ligand to a metal Considered an oxidative addition The reverse of 1,2-insertion Lack of hydrogens??? Coordinatively saturated complexes???
19 14-2 Reactions Involving Modification of Ligands ; abstraction Elimination reactions in which the coordination # of the metal does not change (by the action of an external reagent) and Carbene
20 14-3 Organometallic Catalysts ; catalytic deuteration
21 14-3 Organometallic Catalysts ; hydroformylation
22 14-3 Organometallic Catalysts ; hydroformylation Reactivity and selectivity Linear and branched product HCo(CO) 3 (PBu 3 ), HRh(CO) 2 (PPh 3 ) 2
23 he ynthesis of cetic acid rom ethanol and O 14-3 Organometallic Catalysts ; monsanto acetic acid process
24 14-3 Organometallic Catalysts ; wacker (smidt) process The synthesis of acetaldehyde from ethylene Palladium modified the chemical behavior of ethylene to enable reactions to occur
25 14-3 Organometallic Catalysts ; hydrogenation by wilkinson s catalyst ulky phosphine ligands play n important role in making the omplex selective
26 14-3 Organometallic Catalysts ; hydrogenation by wilkinson s catalyst Selective hydrogenation by Wilkinson s catalyst
27 14-3 Organometallic Catalysts ; olefin methathesis Chauvin mechanism
28 14-3 Organometallic Catalysts ; olefin methathesis More active but more sensitive to oxygen and water Less expensive and less sensitive
29 14-3 Organometallic Catalysts ; olefin methathesis More active and less sensitive to oxygen and water
30 14-3 Organometallic Catalysts ; olefin methathesis More active and less sensitive to oxygen and water Ring-opening polymerization of norbornene Alkyne metathesis
31 14-4 Heterogeneous Catalysts The reactions occurring on the surface of the catalyst may be extremely difficult to ascertain Practically important
32 14-4 Heterogeneous Catalysts ; ziegler-natta polymerizations
33 14-4 Heterogeneous Catalysts ; water gas reaction This reaction occurs at elevated T and P between water and natural sources of carbon Synthesis gas or syn gas Fischer-Tropsch process produce hydrocarbons, alcohols, alkenes, and other products from syn gas Steam reforming natural gas + steam to CO + hydrogen Water gas shift reaction recycling the CO to react further with steam
34 14-4 Heterogeneous Catalysts ; water gas reaction Homogeneous catalysis of water gas shift reaction
35 Homework Exercise 14-1~14-6 Problem 1, 2, 3, 6, 8, 11, 21.!!!!
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