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Topic: Condensation reaction  (Read 4493 times)

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Offline Beatle

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Condensation reaction
« on: October 01, 2009, 04:58:21 AM »
Hi all, I am learning the reactions and have wondered whether or not the aldehyde such as Parformaldehde reacting with say phenylnitropropane, sorry about nomenclature-working on it- phenylnitropropane with Nitro group on the gamma carbon with respect to the aromatic ring of benzene.. Surely that or even a derivative that has 2,3 or4 carbons, is still going to produce an acidic proton apha to the nitro, hence go on attack a carbonal, and if say ammonium acetate would be used, then the OH groups would turn into a leaving group, thau fomring an alkene...
My curiosity is based on the fact, that yes, I have seen smaller nitro derivatives react with numerous aldehydes, but not much when the nitro is big and bulky like whats described, and of course with paraformaldehye..It seems like a useful way for carbon=carbon bonds, as the aldehyde doesn't have to just be formaldehyde, etc// Please take it easy, as I am learning, and perhaps this reaction is problematic be it with cyclic issues, perhaps polymerisaton issues..although if given a choice, between paraformaldehyde and self condensation ie, 1,3 diarylnitropropene, Id go with CHOH. Id imagine this is a DStrap reaction.. Come to think of this though, this potential for the 1,3 diarylnitropropene, is also very interesting.. Perhaps, when reduced, it could inhibit the biochemical respnse, and pathways of amphetamine, which could be good news for drug treatments.. Total guess, but interesting to say the least. HOpefully it is okay to discuus this type of chemistry..I am not at the stage of doing much practical chemistry, but very much into theorecical, and of course the pracs I do with EDU..

One more question, say if an alsdehyde react an amine, secondary, and eventrally results in an imine, or an aldime.. Is the proton of the original aldehyde, post imine formation able to be acidic.. I iknow it would leave charge on an sP2 hybridised Carbon. Yet the carbon double bond with nitrogen, is delta electrophilic, and the same carbon has an R grop plus the proton in question..Ive wondered this for a while, and considering the electorophilic carbon-allthough not as much as C=0, but c=N, and if the alkyl group wasn't donating, then the proton should be somewhat acidic...Perhaps I haven' explained that well, and the post was realy about the initial queerie...
..
« Last Edit: October 01, 2009, 05:11:23 AM by Beatle »

Offline Beatle

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Re: Condensation reaction
« Reply #1 on: October 02, 2009, 05:19:51 AM »
I just read, what I wrote last night, as it was pretty late, and my post has errors, so I just thought I should at least mention that if a Phenyl-2- nitroethane, base promoted condensation, then I think the product would yield 1,3-diaryl-2-nitropropene, and it was this molecule, allthough I am 99.9% confident that it is not going to be bioacive post reduction, in the line of other amphetermine reactions, and would NOT post, if I thought this the case.. Hopefully if the MODS are  more privy, and having a better understanding of this molecule, then I'd imagine this post would go up in flames, and quite rightly..sorry big time, if I am overstepping things here..I am into the chemistry, but there are those who are also, but motivated for BUCKS< and I do not support that cause, yet it is frustrating somewhat not being able to discuss the chem that edges in this direction.. Anyway, if Phenyl-3-nitropropane reacted under the same conditions, I think the product would also be a 1,3 diaryl-3-nitro-2-hexene.. As far as the 1,3-diaryl-2-nitropropene, and the latter, I dare say they could react in the Neff reaction, hence form a ketone, which is not the point of my post, which was primarily wondering if indeed a phenyl-2-nitropropane could react in a K-type condensation, with paraformaldehyde adding an extra carbon at the alpha position to the NO2, I dare say, one would need to consider the acidity of the alpha proton, and also neuclorphilicness of the resulting carbanion.. Anyway,just wanted to clear up a few mistakes I think I made, and perhaps hear about the other ones I have missed..

Offline Beatle

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Re: Condensation reaction
« Reply #2 on: October 02, 2009, 06:26:01 AM »
Woops, He thought the diaryl product was due to some form of rearrangement and selfcondensation, which he wasn't sure on the mechanism, but it would have to be another nitro-aldol type, but final product an alkene...Sorry about that..so it being the phenylnitroethane, reacting with benzaldehyde forming the 1,3-diaryl-2-nitropropene...I think it would form this, but cannot find much in the literature,, come to think of it, I haven't seen much with respect to a phenylnitroalkane type molecule reacting with LITTLE OLD paraformaldehyde, or Acetaldehyde with of course appropiate catalyst, and DS trap to go beyond the nitroaldol... Interesting that I haven't seen much about paraformadehyde as the aldehyde in a Henry or K-type condensation, other than 2-nitroethanol, formed by nitromethane and paraformaldehyde..Perhaps their is a good reason, and my inexperience is not seeing it..
« Last Edit: October 02, 2009, 06:36:21 AM by Beatle »

Offline Beatle

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Re: Condensation reaction
« Reply #3 on: October 02, 2009, 08:39:51 AM »
Double woops, I didn't realise, should of checked, that this particular forum is for graduates. Allthough close I have a few units to complete.. I wont post this elsewhere, due to the potential of Phenylnitroethane reacting with CH2O, hence on reduction a plausible amphetamine...It wasn't my interest, nor my target, just curious, as to the lack of information concerning this possible carbon-carbon reaction..with the bulky Nitroderivitive.. The last thing I want, is to present yet another possible route to that crap..So my bad,,

Att Mods, you probably will, but could you delete all this..Ill graduate, and then be in a position to discuss such chemistry

Beatle..

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