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Topic: Mechanism Trouble  (Read 3445 times)

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Offline Cheemistree8889

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Mechanism Trouble
« on: April 22, 2007, 06:22:19 PM »
Well here it is...I know it's not right.  My problem is the 2nd to last step, i know I cannot form an epoxide like that... any ideas?  It's also done really fast in chemdraw so i would normally shw nonboding electrons and such.
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Offline PRIYA1022

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Re: Mechanism Trouble
« Reply #1 on: April 22, 2007, 06:43:22 PM »
your epoxide looks highly strained....Is that reaction given to you?
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Offline PRIYA1022

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Re: Mechanism Trouble
« Reply #2 on: April 22, 2007, 06:57:18 PM »
Hold on...You have a seven membered ring after the carbocation rearrangement.So I think your mechanism is quite reasonable
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Offline miraculix

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Re: Mechanism Trouble
« Reply #3 on: April 23, 2007, 03:37:25 PM »
As  PRIYA already said, it looks quite okay.
But, I can't see any epoxides somewhere. You're forming a tetrahydrofurane (an epoxide is an three-membered oxygen containing ring. The four-membered analogue is called oxetane). This reaction shouldn't be problematic, eventhough you have many fused rings.


cheers

miraculix
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