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Topic: Grignard reaction with 1,4-dichlorobuthane  (Read 1679 times)

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Offline eurych

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Grignard reaction with 1,4-dichlorobuthane
« on: November 24, 2015, 07:13:16 PM »
Greetings!
I'm having trouble deciding wether the Mg from the Grignard reactive would attach in-between



The problem reads as follows:
"Benzoic anhydride is reacted with Grignard's reactive wich is obtained from 1,4-dichlorobuthane, to finally acidify the medium. Show the mechanism involved".

So, first sorry if it's wrong translated, I'm spanish native though I suspect it is clear. I know the following steps of this reaction, but I don't know if both chlorides are attacked by Mg or just one on one end of the molecule

Cheers! And thank you very much!

Offline beardy

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Re: Grignard reaction with 1,4-dichlorobuthane
« Reply #1 on: November 24, 2015, 09:24:47 PM »
Grignards add twice to esters, acid halides, and anhydrides. This looks initial nucleophilic acyl substituion followed by intramolecular grignard reaction. I could be wrong.



The alcohol is tertiary and is adjacent to a phenyl group. Condensation may take place to allow conjugation.

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