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Topic: Side Products Grignard Reagant  (Read 13353 times)

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Offline Molossus

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Side Products Grignard Reagant
« on: February 10, 2008, 11:26:40 PM »
Anyone know any possible side products you could get from reacting 1) Bromobenzene and Magnesium to form phenylmagnesium bromide and 2) phenylmagnesium bromide and methyl benzoate to form triphenylmethanol . I can't think of any

Offline macman104

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Re: Side Products Grignard Reagant
« Reply #1 on: February 11, 2008, 04:42:24 AM »
I can't see any either, the only thing would be a possible steric factor, but CCl4 can go to triphenylchloride, so I don't think it will be an issue.

Offline AWK

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Re: Side Products Grignard Reagant
« Reply #2 on: February 11, 2008, 06:33:20 AM »
What about reaction of Grignard reagent with traces of water or carbon dioxide from air?
AWK

Offline Sev

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Re: Side Products Grignard Reagant
« Reply #3 on: February 11, 2008, 06:42:30 AM »
« Last Edit: February 11, 2008, 07:36:30 AM by Sev »

Offline macman104

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Re: Side Products Grignard Reagant
« Reply #4 on: February 11, 2008, 01:18:31 PM »
What about reaction of Grignard reagent with traces of water or carbon dioxide from air?
I didn't really count those, as those are sort of possible in any grignard reaction, I was thinking of things specific to the reaction itself.  But yea, biphenyl is a possible byproduct.

Offline jamaal

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Re: Side Products Grignard Reagant
« Reply #5 on: February 11, 2008, 01:33:54 PM »
Hmm..I don't understand how'd you get triphenylmenthanol when you are only reacting two molecules with benzene rings.  As for side products you'd probably get some other derivatives of the alcohol because reactions usuall do not have a 100% yield.  There will also be some sort of organometallic product from the use of the Grignard reagent.

Offline sjb

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Re: Side Products Grignard Reagant
« Reply #6 on: February 11, 2008, 02:36:21 PM »
Hmm..I don't understand how'd you get triphenylmenthanol when you are only reacting two molecules with benzene rings.

Consider what happens when you react a generic ester with a generic Grignard...

S

Offline Sev

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Re: Side Products Grignard Reagant
« Reply #7 on: February 11, 2008, 05:46:56 PM »
See mechanism I posted yesterday.
« Last Edit: February 11, 2008, 05:58:30 PM by Sev »

Offline azmanam

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Re: Side Products Grignard Reagant
« Reply #8 on: February 12, 2008, 08:57:06 AM »
You may also see another "byproduct" experimentally if you don't have a supersoichiometric amount of your nucleophile.
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