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Topic: alkyne question  (Read 4254 times)

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Offline USC organic

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alkyne question
« on: November 09, 2007, 01:20:08 AM »
Is it possible to have a rearrangement (hydride shift specifically) when doing an electrophillic addition like HBr to an alkyne?  If no, why not?
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Offline AWK

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Re: alkyne question
« Reply #1 on: November 09, 2007, 04:10:01 AM »
Quote from: USC organic on November 09, 2007, 01:20:08 AM
Is it possible to have a rearrangement (hydride shift specifically) when doing an electrophillic addition like HBr to an alkyne?  If no, why not?
Did you try to draw a scheme of such shift?
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Offline USC organic

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Re: alkyne question
« Reply #2 on: November 12, 2007, 04:26:25 PM »
yes...i'm not breaking any rules i'm aware of.  Take 4-Methyl-pent-2-yne reacting with HBr for example.  as you protonate the alkyne you can get a carbocation next to the tertiary carbon, could you then get a hydride shift resulting in 4-Bromo-4-methyl-pent-2-ene?  As one example.
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Offline AWK

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Re: alkyne question
« Reply #3 on: November 13, 2007, 01:33:13 AM »
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