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Everything is simple!First, bromine is added on double bond, second nucleophilic substitution of the corresponding bromine anion by the hydroxygroup
Are you sure about the substitution?
Quote from: Nick.Sparrow on November 22, 2007, 05:04:37 PMthat is!I don't agree with this mechanism, I'm with ultrashogun (see below). I think that ring closure occurs by intramolecular attack of the hydroxyl on the bromonium ion. The intramolecular opening of the bromonium ion should be faster than the intermolecular opening with bromide. Unless you are in base and can deprotonate your alcohol I expect the Sn2 on the dibromoalkane will be very, very slow.I realise it's just a typo, but you're missing a carbon in your starting material
The mechanism Dan drew is with a bromonium ion intermediate and than the hydroxyl group attacks to form the ring. What program are you using to draw these mechanisms? I do it by hand and scan them, which can be a PITA.
What program are you using to draw these mechanisms? I do it by hand and scan them, which can be sloppy.
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