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Topic: 2-Bromopropanol  (Read 5457 times)

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Offline AlbertoA

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2-Bromopropanol
« on: May 24, 2011, 10:28:52 PM »
Hello everyone, new in the Forum, first of all, forgive me for my faults at English,  I learnt  it by myself.

My question is:

I star with Propene, and i must synthesize 2-Bromopropanol

What can I do?
I was thinking of adding HBrO but that would give me 1-Bromopropan-2-ol isn't it?


Offline Åke

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Re: 2-Bromopropanol
« Reply #1 on: May 24, 2011, 10:53:50 PM »
You're correct - halohydration will give wrong isomer:

http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch06halohydration.html

http://en.wikipedia.org/wiki/Halohydrin_formation_reaction

Questions to contemplate on:

What is an epoxidation?

What happens when epoxides are treated with HBr? Which carbocation is the most stable?

 ???

// VH

Offline AlbertoA

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Re: 2-Bromopropanol
« Reply #2 on: May 24, 2011, 11:08:22 PM »
perfect! then, 1) MPCBA 2) HBr (diluted) the 2 C will be the most stable carbocation

I've just read about β-Halocarbocations, in that case.. Br2/OH- ?

Offline Åke

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Re: 2-Bromopropanol
« Reply #3 on: May 24, 2011, 11:18:13 PM »
While we are at halohydrins - can a halohydrine serve as starting material? How can Baldwin rules help you?

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