Organometallic Reaction Mechanisms
I have attached two questions involving mechanisms. I am confused on how to approach these problems. Please include explanation and work.
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1. The decomposition of compound A can be accounted by the following mechanisms:
Major products: The bulky Rh-moiety is a good leaving group (show by arrow), which makes the carbonyl carbon quite electron deficient. To compensate that, the double bond comes close to carbonyl carbon and forms a bond (show by arrow). In this way, by metal catalyzed intra-molecular cyclization the pentanone compound is formed, the other product being Rh(PMe3)3Cl.
Minor products: On the other hand, one Me3P group can leave (show by ...
Solution Summary
Logical prediction of reaction mechanisms involving organometallic compounds.
Organometallic Chemistry and Reaction Types
Hi, I need some help with these questions:
5. In the experiment, ligroin may be used as a solvent for the separation of
the product from biphenyl.
a. What is ligroin?
b. Can you suggest an alternative solvent that might be used in
this step?
9. Consider the same reaction as in the previous question (#8) except that in
this case it is carried out with ethyl benzoate. What product would be i
expected in this case?
10. Grignard reagents may be used to prepare other organometallic reagents,
for example, ethylmagnesium bromide reacts with cadmium chloride to
yield diethylcadmium.
2 CH3CH2MgCI + CdCI2 (CH3CH2)2Cd + 2 MgCI2
Indicate the product of the following reactions and name the
organometallic product.
4 CH3MgCI + SiCI4 2 C6HsMgCI + HgCI2 11. para-Nitrobenzaldehyde reacts at a faster rate than benzaldehyde in the
Perkin reaction while p-N,N-dimethylaminobenzaldehyde is much less
reactive toward the same nucleophile. Explain.
18. It is likely that the amount of Grignard reagent your analysis indicates was
formed is greater than the amount of Grignard reagent actually present
just before you added water. Explain.