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Topic: What's the product of these two reactions?  (Read 4717 times)

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Offline kanonsviel

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What's the product of these two reactions?
« on: November 18, 2010, 11:26:28 PM »
For the first one, I have no clue at all...
The second seems like a Darzens reaction, I am not quite sure though.  Should the product be the one I showed in the picture below it? ???

Offline orgopete

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Re: What's the product of these two reactions?
« Reply #1 on: November 19, 2010, 10:51:34 PM »
The first looks like a benzylic acid rearrangement.

Could you please draw the curved arrows showing the formation of the product you are suggesting for the second reaction?
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Offline kanonsviel

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Re: What's the product of these two reactions?
« Reply #2 on: November 20, 2010, 04:30:04 AM »
The first looks like a benzylic acid rearrangement.

Could you please draw the curved arrows showing the formation of the product you are suggesting for the second reaction?

Your suggestion to the first one is most likely the right answer.
For the second one I reconsidered my original thoughts, feeling that it's quite unreasonable for it to go a Darzens mechanism. And maybe I bethought myself too deeper than the problem's intention, for I noticed this reaction might be just a simple SN2... :-[
So, could you please tell me whether the SN2 mechanism giving an ether is reasonable? ???

Offline Rory

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Re: What's the product of these two reactions?
« Reply #3 on: November 20, 2010, 06:23:11 AM »
It's much more simple than you thought. A SN2 product is of course reasonable.

Offline orgopete

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Re: What's the product of these two reactions?
« Reply #4 on: November 20, 2010, 12:51:24 PM »
I suggest learning reaction mechanisms. I can understand how you might have thought the chloroacetate was similar to a an ethyl bromoacetate (or similar reagent) in a Darzens reaction, but the product drawn possessed no chemical logic to its formation. For that reason, it told me that you did not derive that product by application of the reaction mechanism.

If you are having difficulty in learning reaction mechanisms, I suggest you might print out the some example problems posted here:
http://www.curvedarrowpress.com/agocm/inside/sampler/sampler.html

The same problems are repeated at different levels of difficulty so I can assure you that you will be able to solve them. At their most difficult, they are similar to problems in a textbook. There is a benzylic acid rearrangement in the book also.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline kanonsviel

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Re: What's the product of these two reactions?
« Reply #5 on: November 20, 2010, 11:16:06 PM »
I got it, and that's a very good source, thanks very much for your helps :)

Offline SVXX

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Re: What's the product of these two reactions?
« Reply #6 on: November 22, 2010, 01:23:57 PM »

Pardon the non-existent usage of curved arrow notation.
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