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Topic: potassium tert-butoxide  (Read 5556 times)

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Offline plu

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potassium tert-butoxide
« on: April 01, 2006, 12:41:08 PM »
Hello,

If I were to react 3-bromo-2-methylbutane with potassium tert-butoxide in tert-butanol, would the elimination product be predominantly 2-methylbut-2-ene or 3-methylbut-1-ene?  I am thinking the latter since tert-butoxide is such a bulky base but Zaitsev's rule says otherwise...
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Offline tamim83

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Re:potassium tert-butoxide
« Reply #1 on: April 01, 2006, 07:23:24 PM »
Yeah, I am thinking the first product since it is a more substituted alkene even though the base is pretty bulky.  
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Offline maidou13

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Re:potassium tert-butoxide
« Reply #2 on: April 06, 2006, 03:38:42 AM »
I think that the elimination product would be predominantly 2-methylbut-2-ene since 2°carbocation is more stable than 1°carbocation after the migration of one negative hydrogen.
« Last Edit: April 06, 2006, 04:03:58 AM by maidou13 »
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Offline Mitch

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Re:potassium tert-butoxide
« Reply #3 on: April 06, 2006, 08:23:50 PM »
I vote for maidou13's answer.
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