Topic: Problem of the Week - 6/22/09 (Read 2694 times)

azmanam · « **on:** June 21, 2009, 05:26:00 PM »

The other question is still up if anyone wants to take a crack at part 2

http://www.chemicalforums.com/index.php?topic=33985.0

But we'll move on, since I think people are tired of that one

QUESTION: The following reaction is an example of an 'abnormal Michael addition.' Provide a mechanism for this reaction that is consistent with the isotope labeling pattern shown.

Again, watch out for that ¹⁴C. It'll throw you.

orgopete · « **Reply #1 on:** June 22, 2009, 05:59:04 PM »

How about a Michael, intramolecular Claisen, and retro-Claisen?

azmanam · « **Reply #2 on:** June 24, 2009, 01:35:21 AM »

yup, that'll do it. Anyone want to draw up an arrow pushing mechanism? The intermediate after the intramolecular Claisen is pretty neat looking.

plankk · « **Reply #3 on:** June 24, 2009, 04:04:46 AM »

Neat looking? Maybe you have thought about such product

azmanam · « **Reply #4 on:** June 24, 2009, 04:16:10 AM »

no... that's not what the product of the intramolecular Claisen looks like. Try again. The intramolecular Claisen may not be as straightforward as it first seems...

correction:That is the product of an intramolecular Claisen... just not one that gets to the product drawn.

plankk · « **Reply #5 on:** June 24, 2009, 05:47:01 AM »

So maybe this is the interesting us product of the intramolecular Claisen.

azmanam · « **Reply #6 on:** June 24, 2009, 05:50:16 AM »

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Author Topic: Problem of the Week - 6/22/09 (Read 2694 times)

azmanam

Problem of the Week - 6/22/09

orgopete

Re: Problem of the Week - 6/22/09

azmanam

Re: Problem of the Week - 6/22/09

plankk

Re: Problem of the Week - 6/22/09

azmanam

Re: Problem of the Week - 6/22/09

plankk

Re: Problem of the Week - 6/22/09

azmanam

Re: Problem of the Week - 6/22/09