Organic Chemistry

To answer the question asked on the previous blog post. In the base-catalyzed hydrolysis (saponification) of a triglyceride, each ester group reacts with hydroxide ions. The hydroxide attacks the carbonyl carbon, forming a tetrahedral intermediate that collapses to give a carboxylate ion (RCOO⁻) and a glyceroxide leaving group. The glyceroxide is then protonated by water, producing glycerol (HO–CH₂–CH(OH)–CH₂–OH). The overall reaction is: Triacylglycerol + 3 NaOH → Glycerol + 3 Sodium carboxylates (soap molecules). These sodium salts of fatty acids are the “soap” products, while glycerol remains as a neutral, water-soluble by-product. If the mixture is acidified afterward…

Cuando un triéster reacciona con tres equivalentes de hidróxido de sodio (NaOH), cada enlace éster se rompe por la acción del ion hidroxilo, que ataca al carbono del grupo carbonilo. Como resultado, se forman tres sales de carboxilato de sodio (que son los jabones) y glicerol como el otro producto. En el proceso, el ion hidroxilo rompe los enlaces éster, liberando el grupo alcoxi del glicerol, que luego se protona para formar el alcohol final. Después de todas las hidrólisis, los productos que se obtienen son glicerol y tres carboxilatos de sodio (R–COO⁻ Na⁺). Si la mezcla se acidifica al final, esos carboxilatos se convierten en ácidos grasos libres.

This reaction goes through an SN1 mechanism because when the bromine leaves, it forms a really stable benzylic carbocation. That positive charge can spread into the benzene ring through resonance, which makes the intermediate much more stable. An SN2 reaction would not work well here since the carbon attached to bromine is too crowded for a nucleophile to attack directly. Because of that, the reaction naturally follows the SN1 path, where the bond to bromine breaks first and the nucleophile comes in afterward to form the final product.

Este caso es una reacción SN1 y no SN2 por varias razones. Primero, el carbono donde está el bromo es bencílico, y eso hace que cuando el Br se va se forme un carbocatión bencílico muy estable gracias a la resonancia con el anillo aromático. Esa estabilidad es lo que más favorece el mecanismo SN1. Segundo, en un SN2 el nucleófilo tendría que atacar directamente ese carbono, pero como está justo al lado del anillo, hay mucho estorbo estérico y el ataque por la parte de atrás se hace difícil. Por eso el SN2 no es favorable aquí. Además, la reacción está en condiciones que también ayudan al SN1: un disolvente polar prótico como agua o alcohol estabiliza tanto el carbocatió…

Hi! I am trying to solve a process for isolating the product of a reaction from the reagents. Basically there's a salicylic acid derivative created, in the presence of nitromethane, ammonium acetate, in an ethanol solution. Removing the salicylic acid at the end is easy: add water, cool, the salicylic acid drops out of suspension and crystallizes, then either filter or decant + evaporate then wash a couple times in hot water and recrystallize / evaporate to purify. HOWEVER, I believe the ammonium acetate will also drop out of suspension and crystallize, and I need to remove that prior? Or I could try crystallizing the salicylic acid, probably get a bunch of ammonium a…

Hi, I am currently working on a project where I am filtering out small (<0.45 um) polymer microparticles that are slightly hydrophyllic because of the polyvinyl alcohol used as an emulsifier. I'm trying to find the best filter material to use so that if I passed water through the opposite side of the filter, I could recover the particles that were too big to pass through. My options are polyether sulfone, surfactant-free cellulose acetate, Nylon, and cellulose nitrate. Any suggestions?

I read two articles published in 2017 about how abietic acid in resins may react with oil acids in linseed oil to make varnish. Is anyone in this forum familiar with the chemical reactions and catalysts? Thank you.

Hi everyone, I'm working on the fluorination of sulfonamide-linked alcohols using reagents like DAST and Fluolead. My target product is the mono-fluorinated derivative (–CH₂F). smiles code: O=S(=O)(NCCCF)c2ccc(c1ccccc1)cc2 However, I also observe the trifluorinated byproduct (–CF₃). smiles code: O=S(=O)(NCCC(F)(F)F)c2ccc(c1ccccc1)cc2 I’ve been trying to separate the two using flash column chromatography on silica, but they are very close in polarity on TLC (Hexane/Ethyl Acetate) Has anyone had success separating –CH₂F vs. –CF₃ derivatives? Any tips on solvent systems or additives would be really appreciated! Thanks in advance!

Yes, the material is a triacylglycerol, a triglyceride, and the hydrolysis with NaOH gives three carboxylate salts soap and glycerol as the leaving group. Your product is correct glycerol is the expected alcohol after hydrolysis.

So i think this is a hydrolysis of an ester, but I'm not sure. If it is, do I need to add water as a solvent? Most of the examples I have seen with an ester under basic conditions is that there is H2O written alongside the anionic base. Thanks in advance

Es SN1 porque el carbono unido al bromo es terciario, lo que favorece la formación de un carbocatión estable, necesario para el mecanismo SN1.

I have recently started working on a research project related to Belunusov Zhabotinsky reaction by mathematical modeling. Which resources are best because it's details are less available.

Are there any known variations in the chemical composition of formic acid between Oecophylla longinoda and Oecophylla smaragdina? If so, what are the differences, and how might these variations influence their interspecific interactions with other ants in their respective environments?

Hi I am interested in organic chemistry Can someone tell me if https://en.m.wikipedia.org/wiki/Cytosine is a ketone between the N and NH I thought to be a ketone the connected substituents had to be carbon containing as per https://en.m.wikipedia.org/wiki/Ketone

hey, not sure if this belongs in organic chemistry or biochemistry, but I'm researching into whether smells affect a certain species. I need a chemical that is safe to eat and has no taste, but has an odd/bad smell. I know this is kind of difficult due to biology but wondering if it does exist at all. Thanks!

shirts with armpit smell that does not want to leave even after several wash. I experience a weird thing . some of my shirts even after they are washed quickly smell bad even after 1 hour as soon as there is heat i guess. I read a lot about it and figured out this text below that seems to identify the cause . So yes good hygiene, yes keep hair shorts ok but what to do with those shirts. I read on reddit a lot of produc suggested but it is hard to pick the right one since they contain different product i m not familiar with. i want a non toxic product that is not putting my skin in geopardy and that does not contain nanotechnologies…

Hi, I am afraid i am a bit of a chemistry dimwit, but i will ask anyway: I am attempting to dissolve a water soluble compound into an ethanol / propylene glycol solution. The problem is the compound is insoluble in ethanol / glycol, but fully soluble in water. My first attempt was to create a solution in water (successful) then add the ethanol / glycol afterwards....problem is the compound then seems to precipitate out (seems to collect at the bottom of the flask). Is there a way to do this? i thought maybe heat the solution to try and break the bonds? Is there an additive i can add (bearing in mind this is for applying to skin). Sorry if this …

Hi everibody, I need to optimize an extraction procedure for vitamin K1 and vitamins D2 and D3. The results I am obtaining suggest that the addition of a very small amount of water (1% in a mixture composed of 9% EtOH and 90% CO2) improves significally the recovery for vitamins D but not for vitamin K. I am trying to explain that. Both are fat-soluble vitamins so this improvement should not be observed. Is it possible that water can idrolize the double bonds of vitamins D increasing the solubility in ethanol? I believe this is more difficult to happen for vitamin K1 because the double bond included in the aromatic system if very stable becouse of the cheto-enol t…

Hello For further research I need mesoxalate (as acid or salt). It is quite expensive in stores, so I decided to synthesize it in the lab. I tried to hydrolyze alloxan with alkali (NaOH or Ba(OH)2), but I only got alloxanate of the corresponding salt. I also tried to oxidize diethyl malonate with NO2 and NaClO2, but the oxidation did not work at all. Does anyone have a working synthesis method? Or can anyone help me figure out what went wrong?

Hi Everyone Been A while since i have been on this forum. I have been looking at a new starship simulator game upcoming and that has got me thinking about oxygen reclamation in a space scenario. in enclosed spaces like on the ISS they use Lithium Hydroxide to capture and remove co2 while using electrolysis to generate more oxygen. Now I understand that power consumption is an issue with thinking about this, however If you where to capture and separate the C02 from the air then compress it to a liquid under cryogenic temperatures then as a liquid use electrolysis to break it down to Oxygen and carbon monoxide and oxygen then using Cryogenic Distillation…

Hello everyone, We are excited to propose a collaborative effort to validate a groundbreaking bio-chemical process inspired by nature’s efficient hydrogen production mechanisms. Our aim is to test this process within a thermo-chemical system, offering a faster and more efficient alternative to current methane combustion methods. Current hydrogen production techniques, such as steam reforming and electrolysis, face significant challenges due to high energy requirements and environmental concerns. Our innovative approach seeks to overcome these obstacles by leveraging bio-chemical processes for efficient and sustainable hydrogen production. We invite collabor…

Given is the NMR spectrum and molecule. Could you please help me explain the peaks? I am specially confused because it seems the peaks have merged so I am not sure what peaks to count together. On top of that there are multiple secondary alkanes, and I am not sure about their downshift order. Here's what I am thinking so far: 1: triplet - not sure of the chemical shift value 2: doublet of triplet - between 1.2 - 1.7 3: triplet of triplet - between 1.2 - 1.7 4: triplet of triplet - between 1.2 - 1.7 5: triplet - 4 6: Singlet - (11-12) 7: Triplet - (1-5)

The reaction is correct! This is an hydrolysis of ester in basic medium. In a basic medium, the hydrolysis of an ester follows a slightly different mechanism compared to hydrolysis in an acidic medium. In basic hydrolysis, the ester reacts with hydroxide ions (OH−OH−) instead of water molecules. The reaction proceeds through a mechanism called saponification, resulting in the formation of a carboxylate ion and an alcohol. This process is commonly referred to as saponification, and it's often utilized in the production of soaps and detergents, where esters (such as triglycerides) react with strong bases (such as sodium hydroxide) to produce carboxylate ions (soap) and glyc…