Carboxylic acid Puns

Thanks!

https://preview.redd.it/9jiljhtuth981.png?width=772&format=png&auto=webp&s=d384b9d9ab0ba1e03d5f3eb454a2cf987189030a

Ive noticed that a number of my Suzuki reactions when my aryl boronic acid species contains a carboxylic acid my reaction fails. I can usually get it to work either by swapping the catalyst (e.g (dppf)PdCl2 for Pd(PPh3)4) or putting it in the microwave but am unsure why they don't work initially.

My supervisor insists carboxylic acids are the devil and ruin lots of reactions but I'm struggling to find a publication which backs that theory. Ester hydrolysis is also common in my Suzuki's but don't find a problem with reactions going to completion in those cases.

Do carboxylic acids tend to interfere with Suzukis or is it just a coincidence with my reactions?

Edit: thanks for the help everyone :) I think the leading theory is an acetate binding to the Pd (II) complex, stabilising it and therefore deactivating it

Link bhi dal dena video ka

I just wasnt sure about the movement of the protons there to actually form the intermediate because usually the way I imagined it was that if it was a secondary carboxylic acid the Proton in alpha position from the keto group would move to form the enole while the hydrogen leftover from the carboxylic acid becoming co2 would simply take the place of the carboxylic acid group which well couldnt happen here because in the intermediate there aint to place for that so the hydrogen from the carboxylic acid would have to be the hydrogen forming the enole right ? I mean if it was COOD instead of COOH, would the alkohol part of the Enole be OD instead of OH ?

Oh also I mainly came to the question because all examples I could find online were secondary carboxylic acids

also forgive the shitty drawing pls lol

https://preview.redd.it/fb9jud2o6a981.jpg?width=451&format=pjpg&auto=webp&s=b5c457e3db8696079686288f36ef9db126956940

Edit: Ok I actually found an example confirming that its definitely possible - but what about the proton movement, the Idea mentioned above, is that true ? I mean ultimately that D would end up where the COOD was before anyways so one would have to check the intermediate in theory so who knows how possible that is but it would certainly be interesting to me - it seems correct..

Hi all,

I am wondering why we protonate the negatively charged oxygen (abbreviated as proton transfer in the photo below) before kicking out our Cl leaving group? Isn't a negatively charged oxygen better at kicking out our leaving group than a neutral oxygen? I have drawn the incomplete mechanism below, with my question in red. Thank you! :)

https://preview.redd.it/a4f5ecfcfr181.png?width=1536&format=png&auto=webp&s=09ab570d7910c75ae92956506140083bf56cb723

I read in a stack exchange (this one: https://chemistry.stackexchange.com/questions/144422/neutral-fecl3-test) about the importance of a neutral pH in a ferric chloride test for carboxylic acids. I understand why it can't be basic, as ferric hydroxide will instantly crash out. But I don't understand the person's argument if it's too acidic. They label the (RCOO)3Fe complex as both red in neutral conditions and colorless in acidic conditions. Their reaction isn't exactly balanced, so I'm having trouble seeing what's happening. So, what exactly goes wrong in acidic conditions?

Also, we're synthesizing aspirin in lab, and I was wondering if the carboxyl group on the aspirin molecule can complex at all with iron(III), even if it does not affect the color of the solution like salicylic acid does.

Isn't NH3 (no negative charge) more stable than a negative charge, even if it is spread over 2 oxygen atoms?

So if nh3 is more stable than coo-, wouldn't nh4+ be a stronger acid than cooh?

Need advice, please. Is it really necessary to know reac of ethers/epoxides or can I still understand the reactions of Aldehydes and other reactions?? Any 2021 person plz help?

I dont understand how PyBOP coupling works and how to do it on carboxylic acid. Cant find anything about it online. Plz help. And the halogen must be Cl.

I understand the mechanism:

1. deprotonation of COOH group (due to the base)
2. Sn2 reaction (oxygen of COO- attacks the carbon of the alkylhalide, I- leaves)

What i don't really understand is the choice of K2CO3 and DMF. I see this combination A LOT in literature.

K2CO3: I can see that K2CO3 works as a base, but why are these preferred in this kind of reactions? Perhaps because of the solubility of K2CO3 in organic solvents (DMF). After all, carbonates are weak organic bases.

DMF: why use this solvent? It doesnt feel wrong to use for exampleMeOH instead, for example.

https://preview.redd.it/fxo6kh22i2u71.png?width=1420&format=png&auto=webp&s=9ea456fda34c4482c4a1f2e54aecf16466366133

I came across a question where prop-2-en-oic acid(CH2=CH-COOH) was reduced by lialh4. As it is a strong reducing agent I thought the answer was CH3-CH2-CH2OH but the answer came to be CH2=CH-CH2OH. My question is why can't those double bonds be reduced. Thanks for any help.

Hi,
I am learning to navigate around the available databases, and wondering where I am likely to references to structures of small alcohols (glycerol specifically) and carboxylic acid groups (acetic acid). Are they likely to contain esterification reaction data as well? Is there a particular database suited to this type of reactions? Pretty new to using the databases so not sure how much information one can glean from them. Thanks in advance.

Hey all, I’m trying to activate the carboxylic acid on 4-carboxyphenyl boronic acid so I can then react it with an amine (https://www.sigmaaldrich.com/CH/en/product/aldrich/456772) but it’s not soluble in any of the solvents I’ve tried (DCM, EtOAc, ACN, Acetone, water, etc.)!

Do you have any suggestions as to how I could do it? It probably soluble in DMF/DMSO but with the system I’m using (EDC or DCC + NHS) the byproduct will be impossible to isolate/discard.

Any advice is super duper welcome!

Edit: typo

I’m looking at NMR rn and just trying to better understand the difference between electron widrawing groups and donating. I know like aldehydes and CN and COOH and rings are EWG, but I don’t get why. I always just kind of remembered them as such