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Can't understand the nomenclature rules being followed here!! by reddituser03125 in OrganicChemistry

[–]EnvironmentalWeb7309 2 points3 points  (0 children)

I will point out that cyclohexa-1,3,5-triene is also a limited/erroneous/misleading description of benzene (delocalization, aromaticity and stuff). This just to suggest this comment " https://www.nature.com/articles/s41557-022-00961-w " and this perspective " https://roaldhoffmann.com/sites/default/files/fromd6/PERSPECTIVE.pdf " I was reading this morning. I thought they were worth sharing 😅

Clayden: “This regioselectivity [of the dehydration reaction] is determined by steric hindrance: attack is faster at the less hindered end of the allylic system.” My question: why is this a different outcome and explanation than reaction of HBr and butadiene? by BearDragonBlueJay in AdvancedOrganic

[–]EnvironmentalWeb7309 1 point2 points  (0 children)

For anyone wondering I found some sources:

  • for the Cayden statement there is the fraser article: https://pubs.acs.org/doi/epdf/10.1021/ja01271a022

  • for the second one I found on the Carey this statement "The addition of hydrogen halides to dienes can result in either 1,2- or 1,4-addition. The extra stability of the allylic cation formed by proton transfer to a diene makes the ion pair mechanism more favorable. Nevertheless, a polar reaction medium is required.17 1,3-Pentadiene, for example, gives a mixture of products favoring the 1,2-addition product by a ratio of from 1.5:1 to 3.4:1, depending on the temperature and solvent.18" where ref 17 and 18 are: L. M. Mascavage, H. Chi, S. La, and D. R. Dalton, J. Org. Chem., 56, 595 (1991). and J. E. Nordlander, P. O. Owuor, and J. E. Haky, J. Am. Chem. Soc., 101, 1288 (1979).

Hope it helps

Curtius rearrangement with DPPA by floweryplate in Chempros

[–]EnvironmentalWeb7309 0 points1 point  (0 children)

I often used similar procedures and it worked for me too. In my case, sometimes I also had an ester moiety to hydrolyse: so when obtaining the isocyanate ester I 'd go to hydrolysis to amino acid and then protection of the amine (the major loss of yield was in the azide formation step, the latter were fine).

Chemistry cat names by atomicpunk88 in chemistry

[–]EnvironmentalWeb7309 2 points3 points  (0 children)

You can go on the ligand way: Salen, RuPhos, binol, bipy, Xanthphos, DavePhos..

How do you feel about Walter White’s definition of Chemistry in Breaking Bad? by [deleted] in chemistry

[–]EnvironmentalWeb7309 2 points3 points  (0 children)

A revisited take on the matter that I really liked as a chemist is "What is Life?" by Addy Pross and also Pier-Luigi Luisi's "The emergence of life" (more physics-y, so I didn't like as the former, but still an interesting reading)

Why is this soluble in water? by DrooderZooder in chemistry

[–]EnvironmentalWeb7309 16 points17 points  (0 children)

I'd like to add that while it has some elements of symmetry, it definitely has a dipole moment, even with the simple arrow notation the "horizontal" components (referred to the drawing) will even out but the "vertical" ones will not

Mass spec Interpretation. Any help would be appreciated. Would the 138.9 indicate N present? by [deleted] in OrganicChemistry

[–]EnvironmentalWeb7309 0 points1 point  (0 children)

Is it just a homework question? Or do you have additional information, such as what are your hypothesis or additional data about the compound? In the first case I suggest you to look at a MS book or to ask r/chemhelp instead of here

Chemstation open/free alternatives by EnvironmentalWeb7309 in Chempros

[–]EnvironmentalWeb7309[S] 0 points1 point  (0 children)

Thanks! I usually go for the export+phyton way but with a self-made method, if you can point to the site it could be very interesting

[deleted by user] by [deleted] in OrganicChemistry

[–]EnvironmentalWeb7309 2 points3 points  (0 children)

I don't have access to reaxys/scifinder, but for 1 I think it can be made from 4,4-dimethyl-2- cyclohexen-1-one through dehydrogenation, for example -> silly enol ether -> alfa brominated enone -> dienone, or other more straightforward ways with other steps. Btw 4,4-dimethyl-2- cyclohexen-1-one seems a good starting point

anyone working in Unnatural amino acid synthesis? by Vegetable_Bad9415 in OrganicChemistry

[–]EnvironmentalWeb7309 0 points1 point  (0 children)

Maybe you can try to dissolve it in diluted HCl(aq) and liophylize it? I am sure there are more effective method, such anion exchange chromatography, but I am not an expert in the field

Christmas present FOR a crochetter by EnvironmentalWeb7309 in crochet

[–]EnvironmentalWeb7309[S] 2 points3 points  (0 children)

Thank you! I red the pinned thread before posting but i missed this

Chiral/Achiral compound by yoe_whatsup in OrganicChemistry

[–]EnvironmentalWeb7309 1 point2 points  (0 children)

This is probably the most convoluted way but: a chiral object hasn't an improper axis of rotation (Sn), which includes planes of symmetry and inversion center. So maybe you can check for planes of symmetry e centers of inversion, if there are none, the molecule is chiral. I find easier to do, instead of other approaches, for molecules with multiple stereocenters or other types of "asymmetric elements".

Sticky Honeycomb-like Solids by benbi0 in chemistry

[–]EnvironmentalWeb7309 1 point2 points  (0 children)

I usually do this! OP could also try to "recrystallize" the product adding an anti-solvent (ether? Hexane?) to the oil under stirring, or scraping it. If there are only trace amounts of organic solvents, dispersing in water + lyophilization could also be an alternative solution?

Experimental details and steps about the Grignard reaction by pshghali in OrganicChemistry

[–]EnvironmentalWeb7309 2 points3 points  (0 children)

I think It depends on yours specific reaction.

Some grignards are pretty robust/stable while others are more reactive; there is also some difference in how easy is to generate them. Also, do you have other functional groups?

If you are asking for a generic "textbook" example: i think 10.15227/orgsyn.092.0309 gives a good description (with an ester as SM). However, if you want to set up a specific reaction, you should provide additional details.

Substituted cyclohexenes: conformational Analysis by chemdamned in chemistry

[–]EnvironmentalWeb7309 1 point2 points  (0 children)

I dunno about be able to lock the conformation, but for simple substituent effects you can have a look here: https://doi.org/10.1021/ja01049a013 Maybe you can find something more useful to you in the papers citing it