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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: HP on July 31, 2005, 01:57:06 AM

Title: Grignard product
Post by: HP on July 31, 2005, 01:57:06 AM

Hi
I am interesting the properties of the product formed by the reaction of Grignard's reagents with alcochols for example:
Me-MgI + C2H5OH = CH4 + C2H5-OMgI
1.Do C2H5OMgI has basic character and how strong base it is?
2.Can it react further with bromoethyl acetate to form C2H5-OCH2COOEt
In this case if this reaction is possible how could i identify the inorganic salt MgBrI as its mixed salt of magnesium?
Thank you :D

Title: Re:Grignard product
Post by: movies on August 01, 2005, 02:06:08 PM

Yes, Grignards with alcohols would react just the way you showed.  There basicity isn't any greater than a "regular" alkoxide.  alpha-halo carbonyl compounds like bromo ethyl acetate are excellent alkylating agents, although they are a little nasty to work with.

Title: Re:Grignard product
Post by: HP on August 03, 2005, 11:43:04 AM

Yes i alredy know how nasty bromoethylacetate is :'(:)..
The reaction seems really work and i am encouraged.
I have some more questions like: Is the reaction between ROMgI and BrCH2COOEt similar like the Williamson ether formation synthesis like RONa+ R-X...
Thank you for the help.

Title: Re:Grignard product
Post by: movies on August 03, 2005, 12:04:36 PM

Yes, this is very similar to a Williamson ether synthesis.  I think it might have a different name, but I can't remember what it might be.