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Topic: Reaction mechanism  (Read 7998 times)

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Offline Butyllithium

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Reaction mechanism
« on: November 29, 2007, 01:42:19 PM »
What's mechanism of this reaction?What about side reactions?

Butyl.
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Offline ultrashogun

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Re: Reaction mechanism
« Reply #1 on: November 29, 2007, 04:33:49 PM »
First thing is Sn2 of the Br(alpha carbonyl), then MeOH forms an acetal on the carbonyl).
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Offline agrobert

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Re: Reaction mechanism
« Reply #2 on: November 29, 2007, 07:52:28 PM »
Side reactions could involve various Favorskii rearrangements.
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In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline puppy8800

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Re: Reaction mechanism
« Reply #3 on: November 30, 2007, 03:46:18 AM »
« Last Edit: November 30, 2007, 03:58:56 AM by puppy8800 »
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Offline AWK

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Re: Reaction mechanism
« Reply #4 on: November 30, 2007, 03:55:04 AM »
Try and draw mechanism. note - because of geometrical reason SN2 is unfavored
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Offline Dan

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Re: Reaction mechanism
« Reply #5 on: November 30, 2007, 04:12:13 AM »
What about this?

Sorry if it's the same as puppy8800, but I cant view the picture in that link.
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Offline Butyllithium

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Re: Reaction mechanism
« Reply #6 on: November 30, 2007, 04:24:43 AM »
Quote from: Dan on November 30, 2007, 04:12:13 AM
What about this?

Sorry if it's the same as puppy8800, but I cant view the picture in that link.
Yeah,You are right,Dan.Thanks a lot. In this reaction it was proposed that neighboring group participation was favored. And side reaction should be Favorskii rearrangement, to yield pyrrolidine-3-carboxylic acid.

Butyllithium
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Offline puppy8800

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Re: Reaction mechanism
« Reply #7 on: November 30, 2007, 04:32:40 AM »
um..open a new browser and paste that link
mine is a little different
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Offline AWK

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Re: Reaction mechanism
« Reply #8 on: November 30, 2007, 05:00:41 AM »
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Offline ultrashogun

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Re: Reaction mechanism
« Reply #9 on: November 30, 2007, 03:09:13 PM »
Quote from: AWK on November 30, 2007, 03:55:04 AM
Try and draw mechanism. note - because of geometrical reason SN2 is unfavored

Can you please explain why Sn2 is unfavored?
Did you draw scheme? In SN2 nucleophile should attack exactly from back side . Is it possible in this case?
« Last Edit: December 03, 2007, 01:10:30 AM by AWK »
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Offline agrobert

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Re: Reaction mechanism
« Reply #10 on: December 01, 2007, 07:04:33 PM »
It is possible but unlikely with the cyclohexanone conformation and the availability/preference of attack at the carbonyl carbon which has increased delta (+) due to the alpha bromine.  Also this is a classic example for Favorskii type rearrangments.
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In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur
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