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Topic: They will react?{benzaldehyde reactions}  (Read 2144 times)

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Offline asd34

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They will react?{benzaldehyde reactions}
« on: October 08, 2012, 04:00:59 PM »
There is 3 reactions, the substrate is the same, benzaldehyde. The ractions is on the attached image. I didn't find anything about the reaction between ethers and aldehydes. I tried to write the mechanisms with the esters, but then realized that, the alcohol molecule can not eliminate as in the general Claisen condensation, because the deprotonated ester molecule attacks the benzaldehyde to form an alkoxide-ester? I'm not sure. Or it is possible to get a sodium-fenoxid and ester?
« Last Edit: October 08, 2012, 06:12:54 PM by Arkcon »

Offline discodermolide

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Re: They will react?{benzaldehyde reactions}
« Reply #1 on: October 08, 2012, 08:54:40 PM »
The reagent in the first reaction is acetophenone a ketone not an ether.
The are all aldol reactions. What you have to do is figure out if the aldol will eliminate to give the double bond.
I'll draw my products if you wish.
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Offline asd34

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Re: They will react?{benzaldehyde reactions}
« Reply #2 on: October 08, 2012, 09:53:14 PM »
The reagent in the first reaction is acetophenone a ketone not an ether.
The are all aldol reactions. What you have to do is figure out if the aldol will eliminate to give the double bond.
I'll draw my products if you wish.
Then the first will be chalcone and the others is on the picture, but I am not sure about the nomenclature. Is it correct?

Offline discodermolide

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Re: They will react?{benzaldehyde reactions}
« Reply #3 on: October 08, 2012, 09:58:37 PM »
The chalcone is OK
The second one is also OK
The third one you forgot the other aromatic ring.

The name of the top compound in your last drawing should be (E)-4-phenylbut-3-en-2-one.
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Offline asd34

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Re: They will react?{benzaldehyde reactions}
« Reply #4 on: October 08, 2012, 10:00:17 PM »
Thank you discodermolide!

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