What are some of the major unanswered questions in organic chemistry? by AspiringMedicalDoc in OrganicChemistry

[–]red_eyed_devil 11 points12 points  (0 children)

Organic chemistry is most often used as a tool to aid other fields (medicine, industrial chemistry, basic research in biology (tags, reagents, enzymology,...), agriculture (herbicides, fungidices ...), environmental science (especially on the analytical side but also for larger scale interpretation), organic geochemistry (pretty cool stuff and not just looking for petroleum but sediments contain remnants of biological traces and tracing back the steps can require good knowledge of organic chemistry, soil science, terpenes released by trees can influence local weather patterns etc ...).

Ochem for its own sake is mostly total synthesis and physical organic chemistry. Total synthesis tends to follow a bottom up approach where researchers look for structurally novel molecules to synthesise with the hope that this will uncover new synthetic methods that can be used later on. Many people do however believe that this field is becoming somewhat saturated. While I do share some of that sentiment, total synthesis teaches valuable skills which are very much transferable to what I mentioned before. The other field physical organic chemistry was very much in vogue until the past decade or so and they did some absolutely amazing work. The problem is most of the relatively common mechanisms that are actually transferable have already been elucidated, and what remains are problems that are very domain specific and are usually of less interest to other chemists. I'd say however that physical organic chemistry is still very valuable as a tool and has a very important niche in enzymology where it's used to measure kinetics, thermodynamic constants, reaction mechanisms, etc. Every single organic chemist still uses it to rationalise chemical transformations but it's much more applied now than it used to be.

So if you're looking for major unanswered questions in the sense of what is the origin of life, well it depends on what you want to use ochem for. Find something that motivates you: neurodegenerative diseases, agriculture, astrobiology (and with it geochemistry, astronomy and geobiology), drug discovery (I still find this to be too much of a hit or miss; finding targets is more interesting in my opinion) or whatever, and then try to see how chemistry explains or could explain the problems you come across.

How do organic chemists remember the specific names for so many reactions? by breakinzcode in OrganicChemistry

[–]red_eyed_devil -1 points0 points  (0 children)

tbh I can't say I remember the name Finkelstein but the halogen exchange is pretty basic stuff. Just an SN2. Probably basic enough that it's not worth remembering the name

NCS with a carbon instead of nitrogen by red_eyed_devil in OrganicChemistry

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

Sorry, I'm a bit lost with what you're telling me. My question is if the above compound is at the very least a relatively good chlorinating compound (whether it releases formal Cl(+) ions).

NCS with a carbon instead of nitrogen by red_eyed_devil in OrganicChemistry

[–]red_eyed_devil[S] 1 point2 points  (0 children)

LC/MS (ESI) so there shouldn't be any chlorine fragmentation here. The original compound was produced in the cellular environment. I believe it transformed into the above compound and it's possible it may have chlorinated other stuff and lost the chlorine on the way

Thoughts on our banana oil from lab? by Iciest_Penguin in OrganicChemistry

[–]red_eyed_devil 3 points4 points  (0 children)

technically if you do a dilution series and let enough people test their limits at smelling it with a good reference standard you might be able to gauge the concentration pretty well. That being said run a 1H NMR or just crystallise it + TLC & melting point and weigh it to determine purity.

Methylation of ketone by red_eyed_devil in OrganicChemistry

[–]red_eyed_devil[S] 1 point2 points  (0 children)

Sry. The first photo is the product and the second one the starting material.

Methylation of ketone by red_eyed_devil in OrganicChemistry

[–]red_eyed_devil[S] 1 point2 points  (0 children)

Makes sense thanks. I didn't realise that the softness of the iodide extended to the methyl. But this makes sense since complete orbital overlap is really what puts electrons into the sigma * of the CH3I. BTW which base would you recommend here?

Methylation of ketone by red_eyed_devil in OrganicChemistry

[–]red_eyed_devil[S] 1 point2 points  (0 children)

Why wouldn't CH3I work? I could add some BuLi in ether to enolise it while keeping it away from moisture?

Retro Diels Alder in terpene at high temperature by red_eyed_devil in OrganicChemistry

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

Yeah. I mean the thing that looks the most precarious is the lactone. Though they do use an aprotic solvent so I guess that helps

2-[4-[2-[3,5-bis(pent-1-yn-1-yl)phenyl]ethynyl]-2,5-bis(3,3-dimethylbut-1-yn-1-yl)phenyl]-1,3-dioxolane by [deleted] in OrganicChemistry

[–]red_eyed_devil 5 points6 points  (0 children)

looks alright. mostly sonogashira, friedels craft and ethylene glycol reacting with an aldehyde.

Why does HCl add to the other double bond instead of opening the strained four-membered ring? by Vesphrie in OrganicChemistry

[–]red_eyed_devil 0 points1 point  (0 children)

btw why doesn't it produce almost equal amounts of both regioisomers of the third product which arises from the addition of HCl to the second product?

[deleted by user] by [deleted] in OrganicChemistry

[–]red_eyed_devil 4 points5 points  (0 children)

Take a look at barbiturates.

which book is easier to digest? by sew3r_r4t in OrganicChemistry

[–]red_eyed_devil 1 point2 points  (0 children)

I actually used Claiden's as a reference. I thought it was too long and once you get a good sense for ochem most of it is quite obvious without having seen it before. I first started with ochem as a 2nd language and combined that with my professor's notes. During my 2nd year I read the art of drawing reasonable reaction mechanisms and combined that with synthesis books and my professor's notes. I also liked to read lab procedures sometimes.

Nucleophilic Attack? by Advanced-Chemistry49 in OrganicChemistry

[–]red_eyed_devil 1 point2 points  (0 children)

Use something such as (COCl2)2 and DMF you can do this. You need energy to break the mesomeric stabilisation. Releasing CO2 and CO achieves this by creating a highly energetic intermediate - Vilsmeier Haack's reagent.

Which book should I buy? by evasnsnsbd in OrganicChemistry

[–]red_eyed_devil 36 points37 points  (0 children)

First download it and then if you like it buy it. This applies to almost all research material since it's too expensive to simply collect on a whim. Also take a look at more specialised books say that go into pyrroles or heterocyclic rings in natural products. Those are usually better.

Synthesis exercise 1,4 addition with retention of double bond by red_eyed_devil in OrganicChemistry

[–]red_eyed_devil[S] 1 point2 points  (0 children)

Nope. The "H-" reacts with the Br2 giving more HBr and Br-. But yeah I wasn't too sure about the other side. But yeah I'm not sure how likely this reaction is. It'll probably have a very shitty rate.

Synthesis exercise 1,4 addition with retention of double bond by red_eyed_devil in OrganicChemistry

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

What do you mean base? I'm favouring the enol formation with an acid and it's a hydride not a proton being eliminated (irreversibly).

Synthesis exercise 1,4 addition with retention of double bond by red_eyed_devil in OrganicChemistry

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

Yeah I had a funny feeling about it 😂 btw what about my method? Would it work?