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Topic: Unsure of what is occuring in this reaction.  (Read 4686 times)

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Offline Twickel

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Unsure of what is occuring in this reaction.
« on: May 04, 2012, 10:38:27 AM »
page 22 of the attached file,  with the beta-di ester.. bit confused.
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Offline discodermolide

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Re: Unsure of what is occuring in this reaction.
« Reply #1 on: May 04, 2012, 10:41:13 AM »
Quote from: Twickel on May 04, 2012, 10:38:27 AM
page 22 of the attached file,  with the beta-di ester.. bit confused.


So what exactly is your question?
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Offline Doc Oc

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Re: Unsure of what is occuring in this reaction.
« Reply #2 on: May 04, 2012, 11:25:09 AM »
Look up malonic ester.  That should point you in the right direction.
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Offline Twickel

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Re: Unsure of what is occuring in this reaction.
« Reply #3 on: May 04, 2012, 11:32:20 AM »
What mechanism is going on? What is the final product ? For the top most reaction.

I thought the acid hydrolysis forms a product were OH replaces both EtO groups...

Also, in carbonyl chemistry if the reagents are as follows 1)NaOCH3CH2/dry ethanol/heat 2)H30+ what reaction is happening?

« Last Edit: May 04, 2012, 12:10:38 PM by Twickel »
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Offline Babcock_Hall

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Re: Unsure of what is occuring in this reaction.
« Reply #4 on: May 04, 2012, 05:08:29 PM »
Do you mean NaOCH2CH3 (sodium ethoxide)?  Does your compound have any acidic hydrogen atoms?
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Offline Twickel

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Re: Unsure of what is occuring in this reaction.
« Reply #5 on: May 04, 2012, 09:29:48 PM »
Yes, Sodium ethoxide, the structure is Ph-Ch2-CO2CH2CH3

I drew the structures so it makes more sense.. having trouble visualising carbonyl chem reactions

With regards to the condensation reaction, I thought the ketone/aldehyde being added was just a mirror image of the starting product.. what s going on?

« Last Edit: May 04, 2012, 10:30:13 PM by Twickel »
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Offline Twickel

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Re: Unsure of what is occuring in this reaction.
« Reply #6 on: May 04, 2012, 11:09:19 PM »
Sorry for flooding, I tried to edit my last post to change the picture but it would not let me.

i think i figured it out check the bottom mechanism
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Offline orgopete

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Re: Unsure of what is occuring in this reaction.
« Reply #7 on: May 05, 2012, 12:22:58 AM »
Are you trying to do a Claisen?
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Offline Twickel

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Re: Unsure of what is occuring in this reaction.
« Reply #8 on: May 06, 2012, 04:32:33 AM »
In regards to the hydrolyis, I only know how to do base catalysed. Can someone show me hydrolysis via these as the reagents H2O/H+.

Its on page 22 of the attached file

Have they just rotated the bond?
« Last Edit: May 06, 2012, 04:48:16 AM by Twickel »
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