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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: xoggyux on April 26, 2009, 07:54:17 PM

Title: a-Phenylethylamine + CO2
Post by: xoggyux on April 26, 2009, 07:54:17 PM
What is the white compound obtained when a-phenylthylamine reacts with co2.
I think co2 reacts as nucleotide (lone pairs in O) and reacts with phenylthylamine acting as an electrophile. but what I cant figure out is where it reacts? will it substitue the amino group? if so what will be the products.
Title: Re: a-Phenylethylamine + CO2
Post by: ufalynn88 on April 26, 2009, 08:48:22 PM
I think it is more likely for benzene to act as the nucleophile and attack CO2. The resonance structure that illustrates the nucleophilicity of carbon dioxide leaves carbon with a positive charge....I would probably add CO2 para to the other substituent....
Title: Re: a-Phenylethylamine + CO2
Post by: xoggyux on April 26, 2009, 09:44:52 PM
I was checking at my lecture's book and I am trying to do a Diel's-Alder reaction?
Is that the correct approach?
Title: Re: a-Phenylethylamine + CO2
Post by: aldoxime_amine on April 27, 2009, 12:39:01 AM
I was checking at my lecture's book and I am trying to do a Diel's-Alder reaction?
Is that the correct approach?

No, I don't think so. Maybe you would like to see http://en.wikipedia.org/wiki/Kolbe-Schmitt_reaction (http://en.wikipedia.org/wiki/Kolbe-Schmitt_reaction)
Title: Re: a-Phenylethylamine + CO2
Post by: xoggyux on April 27, 2009, 12:47:42 AM
I was checking at my lecture's book and I am trying to do a Diel's-Alder reaction?
Is that the correct approach?

No, I don't think so. Maybe you would like to see http://en.wikipedia.org/wiki/Kolbe-Schmitt_reaction (http://en.wikipedia.org/wiki/Kolbe-Schmitt_reaction)

When I opened the link I was like GREAT THIS IS IT, however the book does say it reacts readily with CO2 from the atmosphere, so there is no basic solution available. Is there any alternate mechanism?
Title: Re: a-Phenylethylamine + CO2
Post by: AWK on April 27, 2009, 01:06:37 AM
CO2 reacts with water to form a weak acid, which with amine can form a salt - carbonate (eg. (NH4)2CO3 is known). At a proper conditions (but not in the air) you can obtain urea of this type RNHCONHR