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Topic: Trouble with mechanism?  (Read 1591 times)

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Offline Starksays

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Trouble with mechanism?
« on: April 01, 2013, 07:14:19 PM »
How would the mechanism of chlorobenzene to a phenol with the dow process work? I understand that somehow the chlorobenzene would become sodium phenoxide and then a phenol but can't seem to find an example of the arrow pushing?

Offline discodermolide

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Re: Trouble with mechanism?
« Reply #1 on: April 02, 2013, 02:55:10 AM »
This process uses high temperatures and very high pressure, I might suggest that under these extreme conditions it is a straight displacement of Cl with hydroxide.
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Offline orgopete

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Re: Trouble with mechanism?
« Reply #2 on: April 02, 2013, 09:07:03 AM »
This process uses high temperatures and very high pressure, I might suggest that under these extreme conditions it is a straight displacement of Cl with hydroxide.

Because other examples undergo an benzyne intermediate, I'd also consider this as a possibility. I don't expect chlorobenzene to undergo an addition-elimination. Perhaps someone could cite an example.
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